fix(auth): store bearer tokens in native credentials

Cargo.lock

@@ -162,6 +162,12 @@ dependencies = [
  "serde",
 ]
 
+[[package]]
+name = "ambient-authority"
+version = "0.0.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e9d4ee0d472d1cd2e28c97dfa124b3d8d992e10eb0a035f33f5d12e3a177ba3b"
+
 [[package]]
 name = "android_system_properties"
 version = "0.1.5"
@@ -1146,6 +1152,48 @@ dependencies = [
  "wayland-client",
 ]
 
+[[package]]
+name = "cap-fs-ext"
+version = "4.0.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d78e5a3368ae89b7cb68186411452b4b9fac8b41be9c19bf3f47c2d2c8e36e6b"
+dependencies = [
+ "cap-primitives",
+ "cap-std",
+ "io-lifetimes 3.0.1",
+ "windows-sys 0.61.2",
+]
+
+[[package]]
+name = "cap-primitives"
+version = "4.0.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "cdadbd7c002d3a484b35243669abdae85a0ebaded5a61117169dc3400f9a7ff0"
+dependencies = [
+ "ambient-authority",
+ "fs-set-times",
+ "io-extras",
+ "io-lifetimes 3.0.1",
+ "ipnet",
+ "maybe-owned",
+ "rustix 1.1.4",
+ "rustix-linux-procfs",
+ "windows-sys 0.61.2",
+ "winx",
+]
+
+[[package]]
+name = "cap-std"
+version = "4.0.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7281235d6e96d3544ca18bba9049be92f4190f8d923e3caef1b5f66cfa752608"
+dependencies = [
+ "cap-primitives",
+ "io-extras",
+ "io-lifetimes 3.0.1",
+ "rustix 1.1.4",
+]
+
 [[package]]
 name = "cbc"
 version = "0.1.2"
@@ -2445,6 +2493,8 @@ name = "ely_app"
 version = "0.1.0"
 dependencies = [
  "ahash",
+ "cap-fs-ext",
+ "cap-std",
  "core-foundation 0.10.0",
  "core-video",
  "directories",
@@ -2454,6 +2504,7 @@ dependencies = [
  "ely_domain",
  "ely_servo_host",
  "ely_sync_client",
+ "fs2",
  "gpui",
  "gpui-component",
  "gpui-component-assets",
@@ -2532,7 +2583,10 @@ dependencies = [
 name = "ely_sync_client"
 version = "0.1.0"
 dependencies = [
+ "apple-native-keyring-store",
  "base64",
+ "cap-fs-ext",
+ "cap-std",
  "chacha20poly1305",
  "ed25519-dalek 2.2.0",
  "ely_domain",
@@ -2541,13 +2595,17 @@ dependencies = [
  "hkdf 0.12.4",
  "hmac 0.12.1",
  "hpke",
- "keyring",
+ "keyring-core",
+ "rustix 1.1.4",
  "serde",
  "serde_json",
  "sha2 0.10.9",
+ "tempfile",
  "thiserror 2.0.18",
  "ureq",
  "uuid",
+ "windows-native-keyring-store",
+ "zbus-secret-service-keyring-store",
  "zeroize",
 ]
 
@@ -3108,6 +3166,17 @@ dependencies = [
  "pkg-config",
 ]
 
+[[package]]
+name = "fs-set-times"
+version = "0.20.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "94e7099f6313ecacbe1256e8ff9d617b75d1bcb16a6fddef94866d225a01a14a"
+dependencies = [
+ "io-lifetimes 2.0.4",
+ "rustix 1.1.4",
+ "windows-sys 0.59.0",
+]
+
 [[package]]
 name = "fs2"
 version = "0.4.3"
@@ -4999,6 +5068,28 @@ dependencies = [
  "rustversion",
 ]
 
+[[package]]
+name = "io-extras"
+version = "0.19.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "20fd6de4ccfcc187e38bc21cfa543cb5a302cb86a8b114eb7f0bf0dc9f8ac00f"
+dependencies = [
+ "io-lifetimes 3.0.1",
+ "windows-sys 0.59.0",
+]
+
+[[package]]
+name = "io-lifetimes"
+version = "2.0.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "06432fb54d3be7964ecd3649233cddf80db2832f47fec34c01f65b3d9d774983"
+
+[[package]]
+name = "io-lifetimes"
+version = "3.0.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2f0fb0570afe1fed943c5c3d4102d5358592d8625fda6a0007fdbe65a92fba96"
+
 [[package]]
 name = "io-surface"
 version = "0.16.1"
@@ -5241,18 +5332,6 @@ dependencies = [
  "unicode-segmentation",
 ]
 
-[[package]]
-name = "keyring"
-version = "4.1.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f6ee8d4dae108d4177d0a0ce241f98acc1ef28e20837bdef43cff4d160cf70fe"
-dependencies = [
- "apple-native-keyring-store",
- "keyring-core",
- "windows-native-keyring-store",
- "zbus-secret-service-keyring-store",
-]
-
 [[package]]
 name = "keyring-core"
 version = "1.0.0"
@@ -5662,6 +5741,12 @@ dependencies = [
  "regex-automata 0.4.14",
 ]
 
+[[package]]
+name = "maybe-owned"
+version = "0.3.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "4facc753ae494aeb6e3c22f839b158aebd4f9270f55cd3c79906c45476c47ab4"
+
 [[package]]
 name = "maybe-rayon"
 version = "0.1.1"
@@ -7872,6 +7957,16 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "rustix-linux-procfs"
+version = "0.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2fc84bf7e9aa16c4f2c758f27412dc9841341e16aa682d9c7ac308fe3ee12056"
+dependencies = [
+ "once_cell",
+ "rustix 1.1.4",
+]
+
 [[package]]
 name = "rustls"
 version = "0.23.40"
@@ -12608,6 +12703,16 @@ version = "0.0.19"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "d135d17ab770252ad95e9a872d365cf3090e3be864a34ab46f48555993efc904"
 
+[[package]]
+name = "winx"
+version = "0.36.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3f3fd376f71958b862e7afb20cfe5a22830e1963462f3a17f49d82a6c1d1f42d"
+dependencies = [
+ "bitflags 2.11.1",
+ "windows-sys 0.59.0",
+]
+
 [[package]]
 name = "wio"
 version = "0.2.2"

Cargo.toml

@@ -19,6 +19,8 @@ rust-version = "1.95"
 
 [workspace.dependencies]
 base64 = "0.22.1"
+cap-fs-ext = "4.0.2"
+cap-std = "4.0.2"
 chacha20poly1305 = "0.11.0"
 directories = "6.0.0"
 dpi = "0.1"
@@ -32,7 +34,8 @@ hkdf = "0.12.4"
 hmac = "0.12.1"
 hpke = { version = "0.14.0", default-features = false, features = ["alloc", "chacha", "getrandom", "x25519"] }
 image = "0.25.10"
-keyring = "4.1.4"
+keyring-core = "1.0.0"
+rustix = "1.1.4"
 servo = { version = "0.4.0", git = "https://github.com/servo/servo.git", rev = "c983c232385edf1170118b24637d2eb2564674d7" }
 sha2 = "0.10.9"
 semver = "1.0.28"

PRD.md

@@ -960,6 +960,7 @@ Better Auth 在 Cloudflare Workers 中初始化，D1 binding 作为 database 传
 - Google/GitHub OAuth 按环境启用。
 - D1 session validation 与自定义 device/session binding。
 - Bearer logout 精确删除当前 D1 session，并级联清理 session device context 与 rebind challenge。
+- Desktop bearer 以 stable `ProfileId` 作为系统凭据 account，Windows 使用 Local persistence；旧明文文件在 credential read-back 与 durable marker 提交后清理，系统凭据不可用时阻断设备加载与 Sync upload。
 - 设备注册、rebind、批准、撤销与 Vault rotation。
 - Signed Sync reset 和 signed account deletion。
 - 管理所有 `/api/auth/*` 路由。
@@ -1571,7 +1572,7 @@ Servo Host 需要实现：
 | ID | 模块 | 验收标准 |
 |---|---|---|
 | S-001 | Sync encryption | 服务端无法解密 Sync payload |
-| S-002 | Keychain | session token 和本地数据库密钥存入系统钥匙串 |
+| S-002 | Keychain | session token 按 stable ProfileId 隔离存入原生系统凭据；明文 legacy token 完成可恢复的一次迁移后删除；凭据不可用时进入独立错误状态并暂停云端动作 |
 | S-003 | Device revoke | 撤销设备后目标 sessions 失效、后续 Sync API 被拒绝、approved revoke 原子轮换 Vault generation |
 | S-004 | Plugin sandbox | 插件无声明权限时无法访问 tabs/bookmarks/history/page |
 | S-005 | Plugin signature | 市场插件必须签名验证通过 |

cloudflare/src/auth.ts

@@ -3,7 +3,7 @@ import { primaryD1Session } from "./bindings.js";
 import { prefixedKvKey } from "./kv_keys.js";
 
 const AUTH_SESSION_CACHE_NAMESPACE = "auth_session_cache";
-const BEARER_TOKEN_PATTERN = /^[A-Za-z0-9._~+/=-]{32,4096}$/;
+const BEARER_TOKEN_PATTERN = /^[A-Za-z0-9._~+/=-]{32,2560}$/;
 const SUBJECT_ID_PATTERN = /^[a-zA-Z0-9._:-]{3,128}$/;
 const DEVICE_ID_PATTERN = /^[a-zA-Z0-9._:-]{3,128}$/;
 const BETTER_AUTH_SESSION_QUERY = `

cloudflare/tests/api_controls.test.ts

@@ -149,6 +149,23 @@ describe("api controls", () => {
     ]);
   });
 
+  it("rejects bearer tokens larger than the native credential contract", async () => {
+    const d1Queries: string[] = [];
+    const response = await withAuthenticatedApiControls(
+      new Request("https://elydora.test/api/devices", {
+        headers: { authorization: `Bearer ${"A".repeat(2561)}` },
+      }),
+      testEnv({ d1: testD1Database({ queries: d1Queries }) }),
+      "devices.list",
+      ["GET"],
+      () => Promise.resolve(jsonResponse({ ok: true }, 200)),
+    );
+
+    assert.equal(response.status, 401);
+    assert.deepEqual(await response.json(), { error: "authorization_invalid" });
+    assert.deepEqual(d1Queries, []);
+  });
+
   it("passes authenticated session context and records subject audit fields", async () => {
     const tokenHash = await authTokenHash(ACCESS_TOKEN);
     const auditEvents: ElyAnalyticsDataPoint[] = [];

crates/ely_app/Cargo.toml

@@ -10,12 +10,15 @@ live-site-smoke = []
 
 [dependencies]
 ahash = "0.8"
+cap-fs-ext.workspace = true
+cap-std.workspace = true
 directories.workspace = true
 ed25519-dalek.workspace = true
 ely_browser_core = { path = "../ely_browser_core" }
 ely_design_system = { path = "../ely_design_system" }
 ely_domain = { path = "../ely_domain" }
 ely_sync_client = { path = "../ely_sync_client" }
+fs2.workspace = true
 gpui.workspace = true
 gpui-component.workspace = true
 gpui-component-assets.workspace = true
@@ -29,6 +32,7 @@ tracing.workspace = true
 tracing-subscriber.workspace = true
 ureq.workspace = true
 url.workspace = true
+uuid.workspace = true
 
 [target.'cfg(target_os = "macos")'.dependencies]
 core-foundation = "0.10"
@@ -37,7 +41,6 @@ io-surface = "0.16"
 mach2 = "0.6"
 objc2-core-foundation = { version = "0.3.2", features = ["CFBase", "CFDictionary", "CFNumber", "CFString"] }
 objc2-io-surface = "0.3.2"
-uuid.workspace = true
 
 [dev-dependencies]
 ely_servo_host = { path = "../ely_servo_host" }

crates/ely_app/src/shell/auth.rs

@@ -139,29 +139,54 @@ impl ElyShell {
     }
 
     /// Drop the persisted bearer token and reset the local form.
-    /// The bearer file is removed synchronously — there is no network
-    /// call to make, the token is the only artefact we own.
     pub(crate) fn submit_sign_out(&mut self, _cx: &mut Context<Self>) {
-        self.auth_flow_phase = AuthFlowPhase::Idle;
-        self.sync_devices.reset();
-        self.sync_retry_at = None;
-        self.clear_pending_cloud_sync_upload();
         let active_profile_id = match active_profile_id_for(&self.state) {
             Some(profile_id) => profile_id,
             None => return,
         };
+        self.auth_flow_phase = AuthFlowPhase::Idle;
+        self.sync_devices.reset();
+        self.sync_upload_scheduled = false;
+        self.sync_retry_at = None;
+        self.clear_pending_cloud_sync_upload();
         let Some(profile_root) = default_profile_data_root() else {
+            self.set_sign_out_error(
+                active_profile_id,
+                "Profile data root is unavailable. Retry sign out.",
+            );
             return;
         };
         let profile_dir = sync_profile_data_dir(&profile_root, &active_profile_id);
-        if let Err(error) = clear_persisted_bearer(&profile_dir) {
+        if let Err(error) = clear_persisted_bearer(
+            &active_profile_id,
+            &profile_dir,
+            &profile_root,
+            self.default_profile_id.as_ref(),
+        ) {
             tracing::warn!(target: "ely::sync", error = %error, "sign-out failed to clear bearer");
+            self.set_sign_out_error(
+                active_profile_id,
+                "System credential access failed. Retry sign out.",
+            );
+            return;
         }
         if let ShellState::Ready(core) = &mut self.state {
             core.set_sync_connection_state(ely_domain::SyncConnectionState::SignedOut);
         }
     }
 
+    fn set_sign_out_error(&mut self, profile_id: ProfileId, message: &str) {
+        self.auth_flow_phase =
+            AuthFlowPhase::Error { profile_id, email: String::new(), message: message.to_string() };
+        if let ShellState::Ready(core) = &mut self.state {
+            core.set_sync_connection_state(
+                ely_domain::SyncConnectionState::CredentialUnavailable {
+                    message: message.to_string(),
+                },
+            );
+        }
+    }
+
     fn read_auth_email_input(&self, cx: &Context<Self>) -> String {
         self.auth_email_input.read(cx).value().to_string()
     }
@@ -201,8 +226,28 @@ fn active_profile_id_for(state: &ShellState) -> Option<ProfileId> {
     core.snapshot().ok().map(|snapshot| snapshot.active_profile_id)
 }
 
-pub(super) fn clear_persisted_bearer(profile_dir: &Path) -> Result<(), SyncClientError> {
+pub(super) fn clear_persisted_bearer(
-    BearerTokenStore::new(profile_dir.join("sync").join("bearer.token")).clear()
+    profile_id: &ProfileId,
+    profile_dir: &Path,
+    profile_root: &Path,
+    default_profile_id: Option<&ProfileId>,
+) -> Result<(), SyncClientError> {
+    bearer_store_for_profile(profile_id, profile_dir, profile_root, default_profile_id).clear()
+}
+
+pub(super) fn bearer_store_for_profile(
+    profile_id: &ProfileId,
+    profile_dir: &Path,
+    profile_root: &Path,
+    default_profile_id: Option<&ProfileId>,
+) -> BearerTokenStore {
+    let store = BearerTokenStore::new(profile_id, profile_dir);
+    if default_profile_id != Some(profile_id) {
+        return store;
+    }
+    store.with_legacy_path(
+        profile_root.join("default").join("servo").join("sync").join("bearer.token"),
+    )
 }
 
 fn spawn_send_otp(profile_id: ProfileId, email: String, tx: Sender<SyncStateUpdate>) {
@@ -252,7 +297,12 @@ fn spawn_verify_otp(
                 }
             };
             let mut engine =
-                match SyncEngine::for_profile_dir(&profile_dir, "ELY", sync_platform_label()) {
+                match SyncEngine::for_profile_dir(
+                    &profile_id,
+                    &profile_dir,
+                    "ELY",
+                    sync_platform_label(),
+                ) {
                     Ok(engine) => engine,
                     Err(error) => {
                         let _ = tx.send(SyncStateUpdate::AuthError {
@@ -284,7 +334,9 @@ mod tests {
     use ely_browser_core::{BrowserCore, InitialBrowserConfig};
     use ely_domain::ProfileId;
 
-    use super::{AuthFlowPhase, active_profile_sync_context_for, normalize_email};
+    use super::{
+        AuthFlowPhase, active_profile_sync_context_for, bearer_store_for_profile, normalize_email,
+    };
     use crate::shell::ShellState;
 
     #[test]
@@ -334,4 +386,57 @@ mod tests {
 
         Ok(())
     }
+
+    #[test]
+    fn default_profile_store_cleans_stable_and_old_legacy_paths()
+    -> Result<(), Box<dyn std::error::Error>> {
+        let directory = tempfile::tempdir()?;
+        let profile_id = ProfileId::new();
+        let profile_dir = directory.path().join(profile_id.as_str()).join("servo");
+        let stable = profile_dir.join("sync/bearer.token");
+        let old = directory.path().join("default/servo/sync/bearer.token");
+        std::fs::create_dir_all(stable.parent().ok_or("missing stable parent")?)?;
+        std::fs::create_dir_all(old.parent().ok_or("missing old parent")?)?;
+        std::fs::write(&stable, "a".repeat(64))?;
+        std::fs::write(&old, "b".repeat(64))?;
+        let store = bearer_store_for_profile(
+            &profile_id,
+            &profile_dir,
+            directory.path(),
+            Some(&profile_id),
+        );
+
+        store.clear_legacy_files()?;
+
+        assert!(!stable.exists());
+        assert!(!old.exists());
+        Ok(())
+    }
+
+    #[test]
+    fn custom_profile_store_leaves_default_legacy_credentials_untouched()
+    -> Result<(), Box<dyn std::error::Error>> {
+        let directory = tempfile::tempdir()?;
+        let profile_id = ProfileId::new();
+        let default_profile_id = ProfileId::new();
+        let profile_dir = directory.path().join(profile_id.as_str()).join("servo");
+        let stable = profile_dir.join("sync/bearer.token");
+        let old_default = directory.path().join("default/servo/sync/bearer.token");
+        std::fs::create_dir_all(stable.parent().ok_or("missing stable parent")?)?;
+        std::fs::create_dir_all(old_default.parent().ok_or("missing default parent")?)?;
+        std::fs::write(&stable, "a".repeat(64))?;
+        std::fs::write(&old_default, "b".repeat(64))?;
+        let store = bearer_store_for_profile(
+            &profile_id,
+            &profile_dir,
+            directory.path(),
+            Some(&default_profile_id),
+        );
+
+        store.clear_legacy_files()?;
+
+        assert!(!stable.exists());
+        assert!(old_default.exists());
+        Ok(())
+    }
 }

crates/ely_app/src/shell/internal_pages/sync.rs

@@ -15,7 +15,6 @@ use super::sync_controls::{
     render_reset_button, render_secondary_button, render_sign_out_button,
 };
 use super::{ElyShell, render_canvas_surface};
-
 impl ElyShell {
     pub(super) fn render_sync_page(
         &mut self,
@@ -23,7 +22,10 @@ impl ElyShell {
         cx: &mut Context<Self>,
     ) -> AnyElement {
         if profile_allows_sync_controls(&snapshot.active_profile_kind)
-            && !matches!(snapshot.sync_status.connection(), SyncConnectionState::SignedOut)
+            && !matches!(
+                snapshot.sync_status.connection(),
+                SyncConnectionState::SignedOut | SyncConnectionState::CredentialUnavailable { .. }
+            )
         {
             self.ensure_sync_devices_loaded(cx);
         }
@@ -37,7 +39,6 @@ impl ElyShell {
         )
     }
 }
-
 fn render_sync_body(
     shell: &mut ElyShell,
     snapshot: &BrowserSnapshot,
@@ -63,11 +64,9 @@ fn render_sync_body(
     )
     .into_any_element()
 }
-
 fn profile_allows_sync_controls(profile_kind: &ProfileKind) -> bool {
     profile_kind == &ProfileKind::Standard
 }
-
 fn render_private_profile_card() -> AnyElement {
     div()
         .p(px(16.0))
@@ -88,7 +87,6 @@ fn render_private_profile_card() -> AnyElement {
         )
         .into_any_element()
 }
-
 fn render_account_card(
     shell: &mut ElyShell,
     snapshot: &BrowserSnapshot,
@@ -102,6 +100,11 @@ fn render_account_card(
             .child(render_card_heading("Account"))
             .children(account_form(shell, &snapshot.active_profile_id, cx))
             .into_any_element(),
+        SyncConnectionState::CredentialUnavailable { message } => card
+            .child(render_card_heading("Account"))
+            .child(render_inline_error(message))
+            .children(account_form(shell, &snapshot.active_profile_id, cx))
+            .into_any_element(),
         SyncConnectionState::SignedIn
         | SyncConnectionState::AwaitingDeviceApproval
         | SyncConnectionState::SyncReady { .. }
@@ -120,11 +123,13 @@ fn render_account_card(
                     .text_color(rgb(colors::ink_3()))
                     .child("End-to-end encrypted"),
             )
+            .when_some(shell.auth_flow_phase.error_message(), |card, message| {
+                card.child(render_inline_error(message))
+            })
             .child(render_devices(shell, cx))
             .into_any_element(),
     }
 }
-
 fn render_devices(shell: &mut ElyShell, cx: &mut Context<ElyShell>) -> AnyElement {
     let loading = shell.sync_devices.is_loading();
     let header =

crates/ely_app/src/shell/mod.rs

@@ -115,6 +115,7 @@ pub struct ElyShell {
     sync_upload_pending: bool,
     sync_upload_pending_merge: Option<PendingMergeUpload>,
     sync_retry_at: Option<std::time::Instant>,
+    default_profile_id: Option<ProfileId>,
     pub(crate) sync_devices: SyncDeviceUiState,
     pub(crate) sync_verification_input: Entity<InputState>,
     pub(crate) auth_email_input: Entity<InputState>,
@@ -126,21 +127,23 @@ pub struct ElyShell {
 
 impl ElyShell {
     pub fn new(window: &mut Window, cx: &mut Context<Self>) -> Self {
+        let mut default_profile_id = None;
         let config = InitialBrowserConfig::ely_defaults()
             .map_err(|error| error.to_string())
             .and_then(|mut config| {
-                config.profile_id = Some(
+                let profile_id = crate::services::profile_identity::default_standard_profile_id()
-                    crate::services::profile_identity::default_standard_profile_id()
+                    .map_err(|error| error.to_string())?;
-                        .map_err(|error| error.to_string())?,
+                config.profile_id = Some(profile_id.clone());
-                );
+                default_profile_id = Some(profile_id);
                 Ok(config)
             });
-        Self::new_with_config(config, window, cx)
+        Self::new_with_config(config, default_profile_id, window, cx)
     }
 
     pub fn new_private(window: &mut Window, cx: &mut Context<Self>) -> Self {
         Self::new_with_config(
             InitialBrowserConfig::private_window().map_err(|error| error.to_string()),
+            None,
             window,
             cx,
         )
@@ -148,6 +151,7 @@ impl ElyShell {
 
     fn new_with_config(
         config: Result<InitialBrowserConfig, String>,
+        default_profile_id: Option<ProfileId>,
         window: &mut Window,
         cx: &mut Context<Self>,
     ) -> Self {
@@ -261,6 +265,7 @@ impl ElyShell {
             sync_upload_pending: false,
             sync_upload_pending_merge: None,
             sync_retry_at: None,
+            default_profile_id,
             sync_devices: SyncDeviceUiState::default(),
             sync_verification_input,
             auth_email_input,

crates/ely_app/src/shell/settings_actions.rs

@@ -9,7 +9,9 @@ use gpui_component::slider::SliderValue;
 
 use crate::services::servo_profile_data::{default_profile_data_root, sync_profile_data_dir};
 
-use super::sync_state::{PendingMergeUpload, SyncStateUpdate, sync_platform_label};
+use super::sync_state::{
+    PendingMergeUpload, SyncStateUpdate, sync_failure_update, sync_platform_label,
+};
 use super::{ElyShell, ShellState};
 
 impl ElyShell {
@@ -255,11 +257,11 @@ impl ElyShell {
     }
 
     fn trigger_cloud_sync_upload_with_merge(&mut self, mut merge: Option<PendingMergeUpload>) {
-        let active_profile_allows_sync = match &self.state {
+        let cloud_sync_enabled = match &self.state {
-            ShellState::Ready(core) => core.active_profile_allows_sync(),
+            ShellState::Ready(core) => core.cloud_sync_upload_enabled(),
             ShellState::StartupError(_) => false,
         };
-        if !active_profile_allows_sync {
+        if !cloud_sync_enabled {
             self.sync_upload_scheduled = false;
             self.clear_pending_cloud_sync_upload();
             return;
@@ -352,6 +354,7 @@ fn run_sync_upload(
     inbox: std::sync::mpsc::Sender<SyncStateUpdate>,
 ) {
     let mut engine = match SyncEngine::for_profile_dir(
+        &profile_id,
         &profile_dir,
         device_name,
         sync_platform_label(),
@@ -360,7 +363,7 @@ fn run_sync_upload(
         Err(error) => {
             let message = error.to_string();
             tracing::warn!(target: "ely::sync", error = %message, "could not initialise sync engine");
-            let _ = inbox.send(SyncStateUpdate::SyncError { profile_id, message });
+            let _ = inbox.send(sync_failure_update(profile_id, error));
             return;
         }
     };
@@ -380,7 +383,10 @@ fn run_sync_upload(
                 device_id = %device_id,
                 "sync device is awaiting approval",
             );
-            let _ = inbox.send(SyncStateUpdate::AwaitingDeviceApproval { profile_id });
+            let _ = inbox.send(SyncStateUpdate::AwaitingDeviceApproval {
+                profile_id,
+                finishes_upload: true,
+            });
         }
         Ok(ely_browser_core::SyncOutcome::RemoteSnapshot {
             snapshot_id,
@@ -454,12 +460,7 @@ fn run_sync_upload(
         Err(error) => {
             let message = error.to_string();
             tracing::warn!(target: "ely::sync", error = %message, "snapshot upload failed");
-            let update = if message.contains("device_not_approved") {
+            let _ = inbox.send(sync_failure_update(profile_id, error));
-                SyncStateUpdate::AwaitingDeviceApproval { profile_id }
-            } else {
-                SyncStateUpdate::SyncError { profile_id, message }
-            };
-            let _ = inbox.send(update);
         }
     }
 }

crates/ely_app/src/shell/sync_devices.rs

@@ -7,7 +7,7 @@ use gpui::Context;
 
 use crate::services::servo_profile_data::{default_profile_data_root, sync_profile_data_dir};
 
-use super::sync_state::sync_platform_label;
+use super::sync_state::{device_failure_update, sync_platform_label};
 use super::{ElyShell, ShellState, sync_state::SyncStateUpdate};
 
 #[derive(Clone, Debug, Default)]
@@ -141,8 +141,12 @@ impl ElyShell {
         }
         let tx = self.sync_inbox_tx.clone();
         spawn_device_task("ely-sync-device-approve", profile_id.clone(), tx, move || {
-            let engine =
+            let engine = SyncEngine::for_profile_dir(
-                SyncEngine::for_profile_dir(&profile_dir, device_name, sync_platform_label())?;
+                &profile_id,
+                &profile_dir,
+                device_name,
+                sync_platform_label(),
+            )?;
             engine.approve_cloud_device(&device_id, &verification_code)?;
             load_devices(profile_id, engine)
         });
@@ -163,8 +167,12 @@ impl ElyShell {
         }
         let tx = self.sync_inbox_tx.clone();
         spawn_device_task("ely-sync-device-revoke", profile_id.clone(), tx, move || {
-            let engine =
+            let engine = SyncEngine::for_profile_dir(
-                SyncEngine::for_profile_dir(&profile_dir, device_name, sync_platform_label())?;
+                &profile_id,
+                &profile_dir,
+                device_name,
+                sync_platform_label(),
+            )?;
             engine.revoke_cloud_device(&device_id)?;
             load_devices(profile_id, engine)
         });
@@ -181,8 +189,12 @@ impl ElyShell {
         }
         let tx = self.sync_inbox_tx.clone();
         spawn_device_task("ely-sync-device-list", profile_id.clone(), tx, move || {
-            let engine =
+            let engine = SyncEngine::for_profile_dir(
-                SyncEngine::for_profile_dir(&profile_dir, device_name, sync_platform_label())?;
+                &profile_id,
+                &profile_dir,
+                device_name,
+                sync_platform_label(),
+            )?;
             load_devices(profile_id, engine)
         });
     }
@@ -191,7 +203,7 @@ impl ElyShell {
         let ShellState::Ready(core) = &self.state else {
             return None;
         };
-        if !core.active_profile_allows_sync() {
+        if !core.cloud_sync_upload_enabled() {
             return None;
         }
         let snapshot = core.snapshot().ok()?;
@@ -225,10 +237,7 @@ fn spawn_device_task<F>(
     let worker_tx = tx.clone();
     let worker_profile_id = profile_id.clone();
     let spawn_result = std::thread::Builder::new().name(thread_name).spawn(move || {
-        let update = task().unwrap_or_else(|error| SyncStateUpdate::DevicesError {
+        let update = task().unwrap_or_else(|error| device_failure_update(worker_profile_id, error));
-            profile_id: worker_profile_id,
-            message: error.to_string(),
-        });
         let _ = worker_tx.send(update);
     });
     if let Err(error) = spawn_result {
@@ -257,4 +266,67 @@ mod tests {
         assert!(state.current_code().is_none());
         assert!(state.error().is_none());
     }
+
+    #[test]
+    fn credential_failures_do_not_finish_an_upload() {
+        let profile_id = ProfileId::new();
+        let update = device_failure_update(
+            profile_id.clone(),
+            ely_sync_client::SyncClientError::BearerCredentialStorage("locked".to_string()),
+        );
+
+        assert!(matches!(
+            update,
+            SyncStateUpdate::CredentialUnavailable {
+                profile_id: owner,
+                finishes_upload: false,
+                ..
+            } if owner == profile_id
+        ));
+    }
+
+    #[test]
+    fn approval_failures_do_not_finish_an_upload() {
+        let profile_id = ProfileId::new();
+        let errors = [
+            ely_sync_client::SyncClientError::DeviceApprovalStatus {
+                device_id: "device-id".to_string(),
+                status: "pending".to_string(),
+            },
+            ely_sync_client::SyncClientError::HttpStatus {
+                endpoint: "/api/sync/devices".to_string(),
+                status: 403,
+                body: r#"{"error":"device_not_approved"}"#.to_string(),
+            },
+        ];
+
+        for error in errors {
+            let update = device_failure_update(profile_id.clone(), error);
+            assert!(matches!(
+                update,
+                SyncStateUpdate::AwaitingDeviceApproval {
+                    profile_id: owner,
+                    finishes_upload: false,
+                } if owner == profile_id
+            ));
+        }
+    }
+
+    #[test]
+    fn operational_failures_stay_in_device_ui_state() {
+        let profile_id = ProfileId::new();
+        let update = device_failure_update(
+            profile_id.clone(),
+            ely_sync_client::SyncClientError::HttpStatus {
+                endpoint: "/api/sync/devices".to_string(),
+                status: 503,
+                body: "unavailable".to_string(),
+            },
+        );
+
+        assert!(matches!(
+            update,
+            SyncStateUpdate::DevicesError { profile_id: owner, .. } if owner == profile_id
+        ));
+    }
 }

crates/ely_app/src/shell/sync_state.rs

@@ -1,11 +1,13 @@
 use std::{path::Path, time::Duration};
 
 use ely_domain::{ProfileId, ProfileKind, SyncConnectionState};
-use ely_sync_client::{AuthenticatedSnapshotHead, DeviceRecord};
+use ely_sync_client::{AuthenticatedSnapshotHead, BearerTokenStore, DeviceRecord};
 use gpui::{Context, Timer};
 
 use super::{ElyShell, ShellState, auth};
 
+mod legacy_sync_migration;
+
 const CLOUD_SYNC_UPLOAD_DEBOUNCE: Duration = Duration::from_millis(750);
 const CAS_RETRY_LIMIT: u8 = 3;
 const CAS_RETRY_DELAY: Duration = Duration::from_secs(2);
@@ -25,11 +27,12 @@ pub(crate) struct PendingMergeUpload {
 #[derive(Clone, Debug)]
 pub(crate) enum SyncStateUpdate {
     SignedOut { profile_id: ProfileId },
-    AwaitingDeviceApproval { profile_id: ProfileId },
+    AwaitingDeviceApproval { profile_id: ProfileId, finishes_upload: bool },
     RemoteSnapshot { profile_id: ProfileId, bytes: Vec<u8>, merge: PendingMergeUpload },
     SyncReady { profile_id: ProfileId, last_synced_at_secs: u64 },
     SyncBusy { profile_id: ProfileId },
     SyncError { profile_id: ProfileId, message: String },
+    CredentialUnavailable { profile_id: ProfileId, message: String, finishes_upload: bool },
     DevicesLoaded { profile_id: ProfileId, devices: Vec<DeviceRecord>, current_code: String },
     DevicesError { profile_id: ProfileId, message: String },
     AuthOtpSent { profile_id: ProfileId, email: String },
@@ -37,6 +40,45 @@ pub(crate) enum SyncStateUpdate {
     AuthError { profile_id: ProfileId, email: String, message: String },
 }
 
+pub(super) fn sync_failure_update(
+    profile_id: ProfileId,
+    error: ely_sync_client::SyncClientError,
+) -> SyncStateUpdate {
+    let message = error.to_string();
+    match error {
+        ely_sync_client::SyncClientError::BearerCredentialStorage(_)
+        | ely_sync_client::SyncClientError::AccountKeyStorage(_)
+        | ely_sync_client::SyncClientError::DeviceKeyStorage(_) => {
+            SyncStateUpdate::CredentialUnavailable { profile_id, message, finishes_upload: true }
+        }
+        ely_sync_client::SyncClientError::DeviceApprovalStatus { .. } => {
+            SyncStateUpdate::AwaitingDeviceApproval { profile_id, finishes_upload: true }
+        }
+        _ if message.contains("device_not_approved") => {
+            SyncStateUpdate::AwaitingDeviceApproval { profile_id, finishes_upload: true }
+        }
+        _ => SyncStateUpdate::SyncError { profile_id, message },
+    }
+}
+
+pub(super) fn device_failure_update(
+    profile_id: ProfileId,
+    error: ely_sync_client::SyncClientError,
+) -> SyncStateUpdate {
+    match sync_failure_update(profile_id, error) {
+        SyncStateUpdate::CredentialUnavailable { profile_id, message, .. } => {
+            SyncStateUpdate::CredentialUnavailable { profile_id, message, finishes_upload: false }
+        }
+        SyncStateUpdate::AwaitingDeviceApproval { profile_id, .. } => {
+            SyncStateUpdate::AwaitingDeviceApproval { profile_id, finishes_upload: false }
+        }
+        SyncStateUpdate::SyncError { profile_id, message } => {
+            SyncStateUpdate::DevicesError { profile_id, message }
+        }
+        update => update,
+    }
+}
+
 /// Stable label for the current OS used by the device registration
 /// payload. Defined once here so every off-thread call site agrees.
 pub(crate) const fn sync_platform_label() -> &'static str {
@@ -128,7 +170,7 @@ impl ElyShell {
         let ShellState::Ready(core) = &mut self.state else {
             return false;
         };
-        probe_initial_sync_state_at(core, &profile_root)
+        probe_initial_sync_state_at(core, &profile_root, self.default_profile_id.as_ref())
     }
 
     /// Drain any sync upload outcomes the off-thread worker pushed
@@ -155,8 +197,8 @@ impl ElyShell {
                         latest_connection = Some(SyncConnectionState::SignedOut);
                     }
                 }
-                SyncStateUpdate::AwaitingDeviceApproval { profile_id } => {
+                SyncStateUpdate::AwaitingDeviceApproval { profile_id, finishes_upload } => {
-                    upload_finished = true;
+                    upload_finished |= finishes_upload;
                     if active_profile_id(&self.state).as_ref() == Some(&profile_id) {
                         latest_connection = Some(SyncConnectionState::AwaitingDeviceApproval);
                     }
@@ -216,6 +258,20 @@ impl ElyShell {
                         latest_connection = Some(SyncConnectionState::SyncError { message });
                     }
                 }
+                SyncStateUpdate::CredentialUnavailable { profile_id, message, finishes_upload } => {
+                    upload_finished |= finishes_upload;
+                    if active_profile_id(&self.state).as_ref() == Some(&profile_id) {
+                        latest_connection =
+                            Some(SyncConnectionState::CredentialUnavailable { message });
+                        self.sync_devices.reset();
+                        self.sync_upload_scheduled = false;
+                        self.sync_retry_at = None;
+                        self.clear_pending_cloud_sync_upload();
+                        trigger_initial_sync = false;
+                        trigger_merged_upload = None;
+                        devices_changed = true;
+                    }
+                }
                 SyncStateUpdate::DevicesLoaded { profile_id, devices, current_code } => {
                     if active_profile_id(&self.state).as_ref() == Some(&profile_id) {
                         self.sync_devices.set_ready(profile_id, devices, current_code);
@@ -296,6 +352,7 @@ fn active_profile_id(state: &ShellState) -> Option<ProfileId> {
 fn probe_initial_sync_state_at(
     core: &mut ely_browser_core::BrowserCore,
     profile_root: &Path,
+    default_profile_id: Option<&ProfileId>,
 ) -> bool {
     let Some(snapshot) = core.snapshot().ok() else {
         return false;
@@ -305,65 +362,46 @@ fn probe_initial_sync_state_at(
         &snapshot.active_profile_id,
     );
     if !core.active_profile_allows_sync() {
-        if let Err(error) = auth::clear_persisted_bearer(&profile_dir) {
+        let store = BearerTokenStore::new(&snapshot.active_profile_id, &profile_dir);
+        if let Err(error) = store.clear_legacy_files() {
             tracing::warn!(target: "ely::sync", error = %error, "private bearer cleanup failed");
         }
         core.set_sync_connection_state(SyncConnectionState::SignedOut);
         return false;
     }
-    if snapshot.active_profile_name == "Default"
+    let is_default_profile = matches!(snapshot.active_profile_kind, ProfileKind::Standard)
-        && matches!(snapshot.active_profile_kind, ProfileKind::Standard)
+        && default_profile_id == Some(&snapshot.active_profile_id);
+    if is_default_profile
+        && let Err(error) =
+            legacy_sync_migration::migrate_default_sync_device(profile_root, &profile_dir)
     {
-        migrate_legacy_default_sync_dir(profile_root, &profile_dir);
-    }
-    let bearer_path = profile_dir.join("sync").join("bearer.token");
-    let bearer_present = bearer_token_file_present(&bearer_path);
-    let state = if bearer_present {
-        ely_domain::SyncConnectionState::SignedIn
-    } else {
-        ely_domain::SyncConnectionState::SignedOut
-    };
-    core.set_sync_connection_state(state);
-    bearer_present
-}
-
-fn bearer_token_file_present(path: &Path) -> bool {
-    std::fs::metadata(path).map(|metadata| metadata.len() > 0).unwrap_or(false)
-}
-
-fn migrate_legacy_default_sync_dir(profile_root: &Path, stable_profile_dir: &Path) {
-    let stable_sync_dir = stable_profile_dir.join("sync");
-    if stable_sync_dir.exists() {
-        return;
-    }
-
-    let candidate = profile_root.join("default").join("servo").join("sync");
-    if !bearer_token_file_present(&candidate.join("bearer.token")) {
-        return;
-    }
-    if let Err(error) = copy_dir_recursive(&candidate, &stable_sync_dir) {
         tracing::warn!(
             target: "ely::sync",
             error = %error,
-            source = %candidate.display(),
             "legacy sync profile migration failed",
         );
     }
-}
+    let store = auth::bearer_store_for_profile(
-
+        &snapshot.active_profile_id,
-fn copy_dir_recursive(source: &Path, destination: &Path) -> std::io::Result<()> {
+        &profile_dir,
-    std::fs::create_dir_all(destination)?;
+        profile_root,
-    for entry in std::fs::read_dir(source)? {
+        default_profile_id,
-        let entry = entry?;
+    );
-        let file_type = entry.file_type()?;
+    let (bearer_present, state) = match store.load() {
-        let destination_path = destination.join(entry.file_name());
+        Ok(Some(_)) => (true, SyncConnectionState::SignedIn),
-        if file_type.is_dir() {
+        Ok(None) => (false, SyncConnectionState::SignedOut),
-            copy_dir_recursive(&entry.path(), &destination_path)?;
+        Err(error) => {
-        } else if file_type.is_file() {
+            tracing::warn!(target: "ely::sync", error = %error, "bearer credential probe failed");
-            std::fs::copy(entry.path(), destination_path)?;
+            (
+                false,
+                SyncConnectionState::CredentialUnavailable {
+                    message: "System credential access failed.".to_string(),
+                },
+            )
         }
-    }
+    };
-    Ok(())
+    core.set_sync_connection_state(state);
+    bearer_present
 }
 
 #[cfg(test)]
@@ -371,59 +409,9 @@ mod tests {
     use ely_browser_core::{BrowserCore, InitialBrowserConfig};
     use ely_domain::SyncConnectionState;
 
-    use super::{
+    use super::{SyncStateUpdate, probe_initial_sync_state_at, sync_failure_update};
-        bearer_token_file_present, migrate_legacy_default_sync_dir, probe_initial_sync_state_at,
-    };
     use crate::services::servo_profile_data::sync_profile_data_dir;
 
-    #[test]
-    fn bearer_token_file_presence_requires_bytes() -> Result<(), Box<dyn std::error::Error>> {
-        let suffix = std::time::SystemTime::now().duration_since(std::time::UNIX_EPOCH)?.as_nanos();
-        let dir = std::env::temp_dir().join(format!("ely-sync-token-probe-{}", suffix));
-        std::fs::create_dir_all(&dir)?;
-        let path = dir.join("bearer.token");
-
-        assert!(!bearer_token_file_present(&path));
-
-        std::fs::write(&path, "")?;
-        assert!(!bearer_token_file_present(&path));
-
-        std::fs::write(&path, "session-token")?;
-        assert!(bearer_token_file_present(&path));
-
-        std::fs::remove_dir_all(dir)?;
-        Ok(())
-    }
-
-    #[test]
-    fn known_default_sync_directory_is_migrated() -> Result<(), Box<dyn std::error::Error>> {
-        let directory = tempfile::tempdir()?;
-        let legacy = directory.path().join("default/servo/sync");
-        let stable = directory.path().join("profile_stable/servo");
-        std::fs::create_dir_all(&legacy)?;
-        std::fs::write(legacy.join("bearer.token"), "default-token")?;
-
-        migrate_legacy_default_sync_dir(directory.path(), &stable);
-
-        assert_eq!(std::fs::read_to_string(stable.join("sync/bearer.token"))?, "default-token");
-        Ok(())
-    }
-
-    #[test]
-    fn custom_profile_bearer_is_ignored_during_default_migration()
-    -> Result<(), Box<dyn std::error::Error>> {
-        let directory = tempfile::tempdir()?;
-        let custom = directory.path().join("profile_custom/servo/sync");
-        let stable = directory.path().join("profile_stable/servo");
-        std::fs::create_dir_all(&custom)?;
-        std::fs::write(custom.join("bearer.token"), "custom-token")?;
-
-        migrate_legacy_default_sync_dir(directory.path(), &stable);
-
-        assert!(!stable.join("sync/bearer.token").exists());
-        Ok(())
-    }
-
     #[test]
     fn private_startup_clears_a_persisted_bearer() -> Result<(), Box<dyn std::error::Error>> {
         let directory = tempfile::tempdir()?;
@@ -436,7 +424,7 @@ mod tests {
         std::fs::write(bearer_path.with_extension("tmp"), "b".repeat(64))?;
         core.set_sync_connection_state(SyncConnectionState::SignedIn);
 
-        assert!(!probe_initial_sync_state_at(&mut core, directory.path()));
+        assert!(!probe_initial_sync_state_at(&mut core, directory.path(), None));
         assert!(!bearer_path.exists());
         assert!(!bearer_path.with_extension("tmp").exists());
         assert_eq!(core.snapshot()?.sync_status.connection(), &SyncConnectionState::SignedOut);
@@ -454,10 +442,56 @@ mod tests {
         std::fs::create_dir_all(bearer_path.parent().ok_or("missing bearer parent")?)?;
         std::fs::write(&bearer_path, "a".repeat(64))?;
 
-        assert!(probe_initial_sync_state_at(&mut core, directory.path()));
+        assert!(probe_initial_sync_state_at(&mut core, directory.path(), Some(&profile_id),));
-        assert!(bearer_path.exists());
+        assert!(!bearer_path.exists());
         assert_eq!(core.snapshot()?.sync_status.connection(), &SyncConnectionState::SignedIn);
 
+        let store = ely_sync_client::BearerTokenStore::new(&profile_id, &profile_dir);
+        assert!(store.load()?.is_some());
+        store.clear()?;
+
         Ok(())
     }
+
+    #[cfg(unix)]
+    #[test]
+    fn credential_probe_failure_enters_unavailable_state() -> Result<(), Box<dyn std::error::Error>>
+    {
+        use std::os::unix::fs::symlink;
+
+        let directory = tempfile::tempdir()?;
+        let mut core = BrowserCore::new(InitialBrowserConfig::ely_defaults()?)?;
+        let profile_id = core.snapshot()?.active_profile_id;
+        let profile_dir = sync_profile_data_dir(directory.path(), &profile_id);
+        let lock = profile_dir.join("sync/bearer.lock");
+        let target = directory.path().join("untrusted.lock");
+        std::fs::create_dir_all(lock.parent().ok_or("missing lock parent")?)?;
+        std::fs::write(&target, "target")?;
+        symlink(&target, &lock)?;
+
+        assert!(!probe_initial_sync_state_at(&mut core, directory.path(), Some(&profile_id),));
+        assert!(matches!(
+            core.snapshot()?.sync_status.connection(),
+            SyncConnectionState::CredentialUnavailable { .. }
+        ));
+        Ok(())
+    }
+
+    #[test]
+    fn credential_storage_failures_use_the_unavailable_update() {
+        let profile_id = ely_domain::ProfileId::new();
+        let update = sync_failure_update(
+            profile_id.clone(),
+            ely_sync_client::SyncClientError::BearerCredentialStorage("locked".to_string()),
+        );
+
+        assert!(matches!(
+            update,
+            SyncStateUpdate::CredentialUnavailable {
+                profile_id: owner,
+                finishes_upload: true,
+                ..
+            } if owner == profile_id
+        ));
+    }
 }

crates/ely_app/src/shell/sync_state/legacy_sync_migration.rs

@@ -0,0 +1,351 @@
+use std::{
+    io::{self, ErrorKind, Read, Write},
+    path::{Component, Path},
+};
+
+use cap_fs_ext::{
+    DirExt, FollowSymlinks, MetadataExt as CrossPlatformMetadataExt, OpenOptionsFollowExt,
+};
+use cap_std::{
+    ambient_authority,
+    fs::{Dir, File, Metadata, OpenOptions, Permissions},
+};
+use ely_sync_client::DeviceIdentity;
+use uuid::Uuid;
+
+const SOURCE_COMPONENTS: [&str; 3] = ["default", "servo", "sync"];
+const DEVICE_FILE: &str = "device.json";
+const COMPLETION_MARKER: &str = ".default-sync-device-migrated-v1";
+const LOCK_FILE: &str = ".default-sync-device-migration.lock";
+const TEMP_PREFIX: &str = ".ely-sync-migration-";
+const COMPLETION_BYTES: &[u8] = b"ely-default-sync-device-migration-v1\n";
+const MAX_DEVICE_BYTES: usize = 16 * 1024;
+
+#[cfg(unix)]
+type ExpectedOwner = u32;
+#[cfg(not(unix))]
+type ExpectedOwner = ();
+
+pub(super) fn migrate_default_sync_device(
+    profile_root: &Path,
+    stable_profile_dir: &Path,
+) -> io::Result<()> {
+    let expected_owner = effective_owner()?;
+    let root = Dir::open_ambient_dir(profile_root, ambient_authority())?;
+    validate_directory(&root, expected_owner)?;
+    let relative_destination = stable_profile_dir
+        .strip_prefix(profile_root)
+        .map_err(|_| invalid_source("stable profile directory escapes the profile root"))?;
+    let stable = open_or_create_path(&root, relative_destination, expected_owner)?;
+    let destination = open_or_create_child(&stable, "sync", expected_owner)?;
+    let _lock = acquire_lock(&destination, expected_owner)?;
+    cleanup_temporary_files(&destination)?;
+
+    if completion_marker_exists(&destination, expected_owner)? {
+        validate_optional_device(&destination, expected_owner)?;
+        return Ok(());
+    }
+    if validate_optional_device(&destination, expected_owner)? {
+        return write_completion_marker(&destination, expected_owner);
+    }
+
+    let Some(source) = open_source_directory(&root, expected_owner)? else {
+        return Ok(());
+    };
+    let Some(bytes) = read_secure_file(&source, DEVICE_FILE, expected_owner, MAX_DEVICE_BYTES)?
+    else {
+        return Ok(());
+    };
+    validate_device_bytes(&bytes)?;
+    persist_bytes_if_absent(
+        &destination,
+        DEVICE_FILE,
+        &bytes,
+        expected_owner,
+        validate_device_bytes,
+    )?;
+    write_completion_marker(&destination, expected_owner)
+}
+
+fn open_source_directory(root: &Dir, owner: ExpectedOwner) -> io::Result<Option<Dir>> {
+    let mut directory = root.try_clone()?;
+    for component in SOURCE_COMPONENTS {
+        directory = match directory.open_dir_nofollow(component) {
+            Ok(child) => child,
+            Err(error) if error.kind() == ErrorKind::NotFound => return Ok(None),
+            Err(error) => return Err(error),
+        };
+        validate_directory(&directory, owner)?;
+    }
+    Ok(Some(directory))
+}
+
+fn open_or_create_path(root: &Dir, path: &Path, owner: ExpectedOwner) -> io::Result<Dir> {
+    let mut directory = root.try_clone()?;
+    for component in path.components() {
+        let Component::Normal(name) = component else {
+            return Err(invalid_source("stable profile directory contains an invalid component"));
+        };
+        directory = open_or_create_child(&directory, name, owner)?;
+    }
+    Ok(directory)
+}
+
+fn open_or_create_child(
+    parent: &Dir,
+    name: impl AsRef<Path>,
+    owner: ExpectedOwner,
+) -> io::Result<Dir> {
+    let name = name.as_ref();
+    let directory = match parent.open_dir_nofollow(name) {
+        Ok(directory) => directory,
+        Err(error) if error.kind() == ErrorKind::NotFound => {
+            match parent.create_dir(name) {
+                Ok(()) => {}
+                Err(error) if error.kind() == ErrorKind::AlreadyExists => {}
+                Err(error) => return Err(error),
+            }
+            let directory = parent.open_dir_nofollow(name)?;
+            set_private_directory_permissions(&directory)?;
+            directory
+        }
+        Err(error) => return Err(error),
+    };
+    validate_directory(&directory, owner)?;
+    Ok(directory)
+}
+
+fn acquire_lock(directory: &Dir, owner: ExpectedOwner) -> io::Result<std::fs::File> {
+    let mut options = private_open_options();
+    options.read(true).write(true).create(true);
+    let file = directory.open_with(LOCK_FILE, &options)?;
+    validate_file(&file, owner)?;
+    set_private_file_permissions(&file)?;
+    let file = file.into_std();
+    fs2::FileExt::lock_exclusive(&file)?;
+    Ok(file)
+}
+
+fn validate_optional_device(directory: &Dir, owner: ExpectedOwner) -> io::Result<bool> {
+    let Some(bytes) = read_secure_file(directory, DEVICE_FILE, owner, MAX_DEVICE_BYTES)? else {
+        return Ok(false);
+    };
+    validate_device_bytes(&bytes)?;
+    Ok(true)
+}
+
+fn completion_marker_exists(directory: &Dir, owner: ExpectedOwner) -> io::Result<bool> {
+    let Some(bytes) =
+        read_secure_file(directory, COMPLETION_MARKER, owner, COMPLETION_BYTES.len())?
+    else {
+        return Ok(false);
+    };
+    validate_marker_bytes(&bytes)?;
+    Ok(true)
+}
+
+fn write_completion_marker(directory: &Dir, owner: ExpectedOwner) -> io::Result<()> {
+    persist_bytes_if_absent(
+        directory,
+        COMPLETION_MARKER,
+        COMPLETION_BYTES,
+        owner,
+        validate_marker_bytes,
+    )
+}
+
+fn persist_bytes_if_absent(
+    directory: &Dir,
+    destination: &str,
+    bytes: &[u8],
+    owner: ExpectedOwner,
+    validate: fn(&[u8]) -> io::Result<()>,
+) -> io::Result<()> {
+    if let Some(existing) = read_secure_file(directory, destination, owner, MAX_DEVICE_BYTES)? {
+        return validate(&existing);
+    }
+
+    let temporary = format!("{TEMP_PREFIX}{}", Uuid::now_v7().simple());
+    let mut options = private_open_options();
+    options.write(true).create_new(true);
+    let mut file = directory.open_with(&temporary, &options)?;
+    validate_file(&file, owner)?;
+    set_private_file_permissions(&file)?;
+    if let Err(error) = file.write_all(bytes).and_then(|()| file.sync_all()) {
+        let _ = directory.remove_file(&temporary);
+        return Err(error);
+    }
+
+    let linked = match directory.hard_link(&temporary, directory, destination) {
+        Ok(()) => true,
+        Err(error) if error.kind() == ErrorKind::AlreadyExists => false,
+        Err(error) => {
+            let _ = directory.remove_file(&temporary);
+            return Err(error);
+        }
+    };
+    remove_file_if_present(directory, &temporary)?;
+    if linked {
+        sync_directory(directory)?;
+    }
+    let existing = read_secure_file(directory, destination, owner, MAX_DEVICE_BYTES)?
+        .ok_or_else(|| invalid_source("migration destination disappeared"))?;
+    validate(&existing)
+}
+
+fn read_secure_file(
+    directory: &Dir,
+    name: &str,
+    owner: ExpectedOwner,
+    maximum_bytes: usize,
+) -> io::Result<Option<Vec<u8>>> {
+    let mut options = private_open_options();
+    options.read(true);
+    let file = match directory.open_with(name, &options) {
+        Ok(file) => file,
+        Err(error) if error.kind() == ErrorKind::NotFound => return Ok(None),
+        Err(error) => return Err(error),
+    };
+    validate_file(&file, owner)?;
+    if file.metadata()?.len() > maximum_bytes as u64 {
+        return Err(invalid_source("migration file exceeds its size limit"));
+    }
+    let mut bytes = Vec::new();
+    file.into_std().take((maximum_bytes + 1) as u64).read_to_end(&mut bytes)?;
+    if bytes.len() > maximum_bytes {
+        return Err(invalid_source("migration file exceeds its size limit"));
+    }
+    Ok(Some(bytes))
+}
+
+fn cleanup_temporary_files(directory: &Dir) -> io::Result<()> {
+    for entry in directory.entries()? {
+        let entry = entry?;
+        let name = entry.file_name();
+        if !name.to_string_lossy().starts_with(TEMP_PREFIX) {
+            continue;
+        }
+        if entry.file_type()?.is_dir() {
+            return Err(invalid_source("migration temporary path is a directory"));
+        }
+        directory.remove_file_or_symlink(name)?;
+    }
+    Ok(())
+}
+
+fn remove_file_if_present(directory: &Dir, name: &str) -> io::Result<()> {
+    match directory.remove_file(name) {
+        Ok(()) => Ok(()),
+        Err(error) if error.kind() == ErrorKind::NotFound => Ok(()),
+        Err(error) => Err(error),
+    }
+}
+
+fn private_open_options() -> OpenOptions {
+    let mut options = OpenOptions::new();
+    options.follow(FollowSymlinks::No);
+    #[cfg(unix)]
+    {
+        use cap_std::fs::OpenOptionsExt;
+        options.mode(0o600);
+    }
+    options
+}
+
+fn validate_directory(directory: &Dir, owner: ExpectedOwner) -> io::Result<()> {
+    let metadata = directory.dir_metadata()?;
+    if !metadata.is_dir() {
+        return Err(invalid_source("migration path is not a directory"));
+    }
+    validate_owner_and_mode(&metadata, owner)
+}
+
+fn validate_file(file: &File, owner: ExpectedOwner) -> io::Result<()> {
+    let metadata = file.metadata()?;
+    if !metadata.is_file() || CrossPlatformMetadataExt::nlink(&metadata) != 1 {
+        return Err(invalid_source("migration file link state is invalid"));
+    }
+    validate_owner_and_mode(&metadata, owner)
+}
+
+#[cfg(unix)]
+fn validate_owner_and_mode(metadata: &Metadata, owner: ExpectedOwner) -> io::Result<()> {
+    use cap_std::fs::{MetadataExt, PermissionsExt};
+    if metadata.uid() != owner || metadata.permissions().mode() & 0o022 != 0 {
+        return Err(io::Error::new(
+            ErrorKind::PermissionDenied,
+            "migration path ownership or permissions are invalid",
+        ));
+    }
+    Ok(())
+}
+
+#[cfg(not(unix))]
+const fn validate_owner_and_mode(_metadata: &Metadata, _owner: ExpectedOwner) -> io::Result<()> {
+    Ok(())
+}
+
+#[cfg(unix)]
+fn effective_owner() -> io::Result<ExpectedOwner> {
+    use std::os::unix::fs::MetadataExt;
+    let probe = tempfile::NamedTempFile::new()?;
+    Ok(probe.as_file().metadata()?.uid())
+}
+
+#[cfg(not(unix))]
+const fn effective_owner() -> io::Result<ExpectedOwner> {
+    Ok(())
+}
+
+#[cfg(unix)]
+fn set_private_directory_permissions(directory: &Dir) -> io::Result<()> {
+    use cap_std::fs::PermissionsExt;
+    directory.set_permissions(".", Permissions::from_mode(0o700))
+}
+
+#[cfg(not(unix))]
+const fn set_private_directory_permissions(_directory: &Dir) -> io::Result<()> {
+    Ok(())
+}
+
+#[cfg(unix)]
+fn set_private_file_permissions(file: &File) -> io::Result<()> {
+    use cap_std::fs::PermissionsExt;
+    file.set_permissions(Permissions::from_mode(0o600))
+}
+
+#[cfg(not(unix))]
+const fn set_private_file_permissions(_file: &File) -> io::Result<()> {
+    Ok(())
+}
+
+#[cfg(unix)]
+fn sync_directory(directory: &Dir) -> io::Result<()> {
+    directory.try_clone()?.into_std_file().sync_all()
+}
+
+#[cfg(not(unix))]
+const fn sync_directory(_directory: &Dir) -> io::Result<()> {
+    Ok(())
+}
+
+fn validate_device_bytes(bytes: &[u8]) -> io::Result<()> {
+    DeviceIdentity::validate_stored_bytes(bytes, Path::new(DEVICE_FILE))
+        .map_err(|error| invalid_source(error.to_string()))
+}
+
+fn validate_marker_bytes(bytes: &[u8]) -> io::Result<()> {
+    if bytes == COMPLETION_BYTES {
+        Ok(())
+    } else {
+        Err(invalid_source("legacy sync migration marker is invalid"))
+    }
+}
+
+fn invalid_source(message: impl Into<String>) -> io::Error {
+    io::Error::new(ErrorKind::InvalidData, message.into())
+}
+
+#[cfg(test)]
+#[path = "legacy_sync_migration_tests.rs"]
+mod tests;

crates/ely_app/src/shell/sync_state/legacy_sync_migration_tests.rs

@@ -0,0 +1,159 @@
+use std::{fs, path::Path};
+
+use super::*;
+
+const PUBLIC_KEY: &str = "d75a980182b10ab7d54bfed3c964073a0ee172f3daa62325af021a68f707511a";
+
+#[test]
+fn copies_only_valid_device_once() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let source = source_dir(directory.path());
+    let stable = stable_dir(directory.path());
+    fs::create_dir_all(source.join("nested"))?;
+    fs::write(source.join(DEVICE_FILE), device_bytes("Legacy"))?;
+    fs::write(source.join("bearer.token"), "secret")?;
+    fs::write(source.join("other.json"), "other")?;
+    migrate_default_sync_device(directory.path(), &stable)?;
+    let destination = stable.join("sync");
+    assert_eq!(fs::read(destination.join(DEVICE_FILE))?, device_bytes("Legacy"));
+    assert!(!destination.join("bearer.token").exists());
+    assert!(!destination.join("other.json").exists());
+    assert!(!destination.join("nested").exists());
+    fs::remove_file(destination.join(DEVICE_FILE))?;
+    fs::write(source.join(DEVICE_FILE), device_bytes("Changed"))?;
+    migrate_default_sync_device(directory.path(), &stable)?;
+    assert!(!destination.join(DEVICE_FILE).exists());
+    Ok(())
+}
+
+#[test]
+fn preserves_a_valid_existing_destination() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let source = source_dir(directory.path());
+    let stable = stable_dir(directory.path());
+    fs::create_dir_all(&source)?;
+    fs::create_dir_all(stable.join("sync"))?;
+    fs::write(source.join(DEVICE_FILE), device_bytes("Legacy"))?;
+    fs::write(stable.join("sync/device.json"), device_bytes("Current"))?;
+    migrate_default_sync_device(directory.path(), &stable)?;
+    assert_eq!(fs::read(stable.join("sync/device.json"))?, device_bytes("Current"));
+    assert!(stable.join("sync").join(COMPLETION_MARKER).exists());
+    Ok(())
+}
+
+#[test]
+fn missing_source_retries_later() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let stable = stable_dir(directory.path());
+    migrate_default_sync_device(directory.path(), &stable)?;
+    assert!(!stable.join("sync").join(COMPLETION_MARKER).exists());
+    let source = source_dir(directory.path());
+    fs::create_dir_all(&source)?;
+    fs::write(source.join(DEVICE_FILE), device_bytes("Late"))?;
+    migrate_default_sync_device(directory.path(), &stable)?;
+    assert_eq!(fs::read(stable.join("sync/device.json"))?, device_bytes("Late"));
+    Ok(())
+}
+
+#[test]
+fn rejects_invalid_and_oversized_sources() -> Result<(), Box<dyn std::error::Error>> {
+    for bytes in [b"{}".to_vec(), vec![b'a'; MAX_DEVICE_BYTES + 1]] {
+        let directory = tempfile::tempdir()?;
+        let source = source_dir(directory.path());
+        let stable = stable_dir(directory.path());
+        fs::create_dir_all(&source)?;
+        fs::write(source.join(DEVICE_FILE), bytes)?;
+        assert!(migrate_default_sync_device(directory.path(), &stable).is_err());
+        assert!(!stable.join("sync").join(COMPLETION_MARKER).exists());
+    }
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn rejects_source_ancestor_and_destination_links() -> Result<(), Box<dyn std::error::Error>> {
+    use std::os::unix::fs::symlink;
+
+    for linked_component in 0..SOURCE_COMPONENTS.len() {
+        let directory = tempfile::tempdir()?;
+        let target = directory.path().join("source-target");
+        let mut real = target.clone();
+        for component in &SOURCE_COMPONENTS[linked_component + 1..] {
+            real.push(component);
+        }
+        fs::create_dir_all(&real)?;
+        fs::write(real.join(DEVICE_FILE), device_bytes("Linked"))?;
+        let mut link = directory.path().to_path_buf();
+        for component in &SOURCE_COMPONENTS[..linked_component] {
+            link.push(component);
+        }
+        fs::create_dir_all(&link)?;
+        link.push(SOURCE_COMPONENTS[linked_component]);
+        symlink(&target, &link)?;
+        assert!(
+            migrate_default_sync_device(directory.path(), &stable_dir(directory.path())).is_err()
+        );
+    }
+    let directory = tempfile::tempdir()?;
+    let stable = stable_dir(directory.path());
+    fs::create_dir_all(&stable)?;
+    symlink(directory.path().join("elsewhere"), stable.join("sync"))?;
+    assert!(migrate_default_sync_device(directory.path(), &stable).is_err());
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn rejects_linked_destination_files() -> Result<(), Box<dyn std::error::Error>> {
+    use std::os::unix::fs::symlink;
+
+    for name in [DEVICE_FILE, COMPLETION_MARKER] {
+        let directory = tempfile::tempdir()?;
+        let stable = stable_dir(directory.path());
+        let destination = stable.join("sync");
+        let target = directory.path().join("target");
+        fs::create_dir_all(&destination)?;
+        fs::write(
+            &target,
+            if name == DEVICE_FILE { device_bytes("Target") } else { COMPLETION_BYTES.to_vec() },
+        )?;
+        symlink(&target, destination.join(name))?;
+        assert!(migrate_default_sync_device(directory.path(), &stable).is_err());
+    }
+    Ok(())
+}
+
+#[test]
+fn rejects_hardlinked_source_and_destination() -> Result<(), Box<dyn std::error::Error>> {
+    for destination_link in [false, true] {
+        let directory = tempfile::tempdir()?;
+        let source = source_dir(directory.path());
+        let stable = stable_dir(directory.path());
+        let target = directory.path().join("target.json");
+        fs::create_dir_all(&source)?;
+        fs::write(&target, device_bytes("Target"))?;
+        if destination_link {
+            fs::create_dir_all(stable.join("sync"))?;
+            fs::hard_link(&target, stable.join("sync/device.json"))?;
+        } else {
+            fs::hard_link(&target, source.join(DEVICE_FILE))?;
+        }
+        assert!(migrate_default_sync_device(directory.path(), &stable).is_err());
+    }
+    Ok(())
+}
+
+fn source_dir(root: &Path) -> std::path::PathBuf {
+    root.join("default/servo/sync")
+}
+
+fn stable_dir(root: &Path) -> std::path::PathBuf {
+    root.join("profile_stable/servo")
+}
+
+fn device_bytes(name: &str) -> Vec<u8> {
+    format!(
+        r#"{{"device_id":"ely-legacy-device","public_key":"{PUBLIC_KEY}","device_name":"{name}","platform":"macos"}}"#,
+    )
+    .into_bytes()
+}

crates/ely_browser_core/src/sync_engine.rs

@@ -3,6 +3,7 @@ use std::{
     time::{SystemTime, UNIX_EPOCH},
 };
 
+use ely_domain::ProfileId;
 use ely_sync_client::{
     AccountKey, ApiClientConfig, AuthenticatedSnapshotHead, BearerToken, BearerTokenStore,
     DeviceIdentity, SNAPSHOT_ENCRYPTION_VERSION, SnapshotCryptoContext, SnapshotDownloadResult,
@@ -34,6 +35,7 @@ impl SyncEngine {
     /// fresh device identity on first use, then keeps it stable across
     /// runs so the server's `user_devices` row stays bound.
     pub fn for_profile_dir(
+        profile_id: &ProfileId,
         profile_data_dir: &Path,
         device_name: impl Into<String>,
         platform: impl Into<String>,
@@ -46,7 +48,7 @@ impl SyncEngine {
             .join(".sync-key-locks");
         let identity =
             DeviceIdentity::load_or_create(&sync_dir.join("device.json"), device_name, platform)?;
-        let bearer_store = BearerTokenStore::new(sync_dir.join("bearer.token"));
+        let bearer_store = BearerTokenStore::new(profile_id, profile_data_dir);
         Ok(Self {
             api_config: ApiClientConfig::production(),
             bearer_store,
@@ -60,10 +62,6 @@ impl SyncEngine {
         &self.identity
     }
 
-    pub fn bearer_path(&self) -> &Path {
-        self.bearer_store.path()
-    }
-
     pub fn last_outcome(&self) -> Option<&SyncOutcome> {
         self.last_outcome.as_ref()
     }
@@ -436,6 +434,7 @@ fn device_registration_idempotency_key(identity: &DeviceIdentity) -> String {
 
 #[derive(Debug)]
 pub struct SyncEngineBuilder {
+    pub profile_id: ProfileId,
     pub profile_data_dir: PathBuf,
     pub device_name: String,
     pub platform: String,
@@ -443,7 +442,12 @@ pub struct SyncEngineBuilder {
 
 impl SyncEngineBuilder {
     pub fn build(self) -> Result<SyncEngine, SyncClientError> {
-        SyncEngine::for_profile_dir(&self.profile_data_dir, self.device_name, self.platform)
+        SyncEngine::for_profile_dir(
+            &self.profile_id,
+            &self.profile_data_dir,
+            self.device_name,
+            self.platform,
+        )
     }
 }
 

crates/ely_browser_core/tests/sync.rs

@@ -38,6 +38,17 @@ fn default_sync_status_reflects_local_browser_state() -> Result<(), Box<dyn Erro
     Ok(())
 }
 
+#[test]
+fn unavailable_credentials_disable_cloud_uploads() -> Result<(), Box<dyn Error>> {
+    let mut core = BrowserCore::new(InitialBrowserConfig::ely_defaults()?)?;
+    core.set_sync_connection_state(SyncConnectionState::CredentialUnavailable {
+        message: "credential unavailable".to_string(),
+    });
+
+    assert!(!core.cloud_sync_upload_enabled());
+    Ok(())
+}
+
 #[test]
 fn sync_object_policy_pauses_object_kind() -> Result<(), Box<dyn Error>> {
     let mut core = BrowserCore::new(InitialBrowserConfig::ely_defaults()?)?;

crates/ely_domain/src/sync.rs

@@ -13,6 +13,7 @@
 #[derive(Clone, Debug, Eq, PartialEq)]
 pub enum SyncConnectionState {
     SignedOut,
+    CredentialUnavailable { message: String },
     SignedIn,
     AwaitingDeviceApproval,
     SyncReady { last_synced_at_secs: u64 },
@@ -104,7 +105,8 @@ impl SyncStatus {
     #[must_use]
     pub fn new(connection: SyncConnectionState, objects: Vec<SyncObjectStatus>) -> Self {
         let failed_objects = match &connection {
-            SyncConnectionState::SyncError { .. } => 1,
+            SyncConnectionState::CredentialUnavailable { .. }
+            | SyncConnectionState::SyncError { .. } => 1,
             _ => 0,
         };
         Self { connection, pending_objects: 0, failed_objects, objects }

crates/ely_sync_client/Cargo.toml

@@ -7,6 +7,8 @@ rust-version.workspace = true
 
 [dependencies]
 base64.workspace = true
+cap-fs-ext.workspace = true
+cap-std.workspace = true
 chacha20poly1305.workspace = true
 ed25519-dalek.workspace = true
 ely_domain = { path = "../ely_domain" }
@@ -15,7 +17,7 @@ getrandom.workspace = true
 hkdf.workspace = true
 hmac.workspace = true
 hpke.workspace = true
-keyring.workspace = true
+keyring-core.workspace = true
 serde = { workspace = true }
 serde_json = { workspace = true }
 sha2 = { workspace = true }
@@ -24,5 +26,20 @@ ureq = { workspace = true, features = ["json"] }
 uuid = { workspace = true }
 zeroize.workspace = true
 
+[dev-dependencies]
+tempfile.workspace = true
+
+[target.'cfg(unix)'.dependencies]
+rustix = { workspace = true, features = ["process"] }
+
+[target.'cfg(target_os = "macos")'.dependencies]
+apple-native-keyring-store = { version = "1.0.0", features = ["keychain"] }
+
+[target.'cfg(target_os = "windows")'.dependencies]
+windows-native-keyring-store = "1.1.0"
+
+[target.'cfg(all(unix, not(any(target_os = "macos", target_os = "ios", target_os = "android"))))'.dependencies]
+zbus-secret-service-keyring-store = { version = "1.0.0", features = ["crypto-rust"] }
+
 [lints]
 workspace = true

crates/ely_sync_client/src/auth.rs

@@ -1,31 +1,56 @@
 use std::{
-    fs,
+    fmt,
-    io::{self, ErrorKind},
     path::{Path, PathBuf},
 };
 
-use crate::error::SyncClientError;
+use ely_domain::ProfileId;
+use fs2::FileExt;
+use zeroize::Zeroizing;
 
-/// Better Auth bearer token issued by `https://<base>/api/auth/*`. The
+use crate::{
-/// token grants access to the per-user `withAuthenticatedApiControls`
+    auth_files::{
-/// routes and, once the device is bound to the session, to the
+        ensure_migration_marker, migration_marker_exists, open_lock_file, read_legacy_bytes,
-/// `withApprovedDeviceApiControls` routes used by sync.
+        remove_file_if_present,
-#[derive(Clone, Debug, Eq, PartialEq)]
+    },
-pub struct BearerToken(String);
+    credential_store::{clear_secret, load_secret, save_secret},
+    error::SyncClientError,
+};
+
+const KEYCHAIN_SERVICE: &str = "com.elydora.ely-browser.auth.bearer.v1";
+const MIN_BEARER_TOKEN_BYTES: usize = 32;
+const MAX_BEARER_TOKEN_BYTES: usize = 2560;
+
+/// Better Auth bearer token issued by `https://<base>/api/auth/*`.
+pub struct BearerToken(Zeroizing<String>);
+
+impl Clone for BearerToken {
+    fn clone(&self) -> Self {
+        Self(Zeroizing::new(self.as_str().to_string()))
+    }
+}
+
+impl fmt::Debug for BearerToken {
+    fn fmt(&self, formatter: &mut fmt::Formatter<'_>) -> fmt::Result {
+        formatter.write_str("BearerToken([REDACTED])")
+    }
+}
+
+impl PartialEq for BearerToken {
+    fn eq(&self, other: &Self) -> bool {
+        self.as_str() == other.as_str()
+    }
+}
+
+impl Eq for BearerToken {}
 
 impl BearerToken {
-    /// Construct a token from an existing string. Trims whitespace and
-    /// enforces the same character envelope the worker validates so
-    /// obviously-malformed tokens fail before we hit the network.
     pub fn new(value: impl Into<String>) -> Result<Self, SyncClientError> {
-        let value = value.into();
+        let value = Zeroizing::new(value.into());
         let trimmed = value.trim();
         if trimmed.is_empty() || !is_better_auth_bearer(trimmed) {
-            return Err(SyncClientError::TokenStorage(
+            return Err(storage_error("bearer token is not a Better Auth session token"));
-                "bearer token is not a Better Auth session token".to_string(),
-            ));
         }
-        Ok(Self(trimmed.to_string()))
+        Ok(Self(Zeroizing::new(trimmed.to_string())))
     }
 
     pub fn as_str(&self) -> &str {
@@ -34,7 +59,7 @@ impl BearerToken {
 }
 
 fn is_better_auth_bearer(token: &str) -> bool {
-    let length_ok = (32..=4096).contains(&token.len());
+    let length_ok = (MIN_BEARER_TOKEN_BYTES..=MAX_BEARER_TOKEN_BYTES).contains(&token.len());
     let charset_ok = token
         .as_bytes()
         .iter()
@@ -42,100 +67,238 @@ fn is_better_auth_bearer(token: &str) -> bool {
     length_ok && charset_ok
 }
 
-/// File-backed bearer token store. Lives in the per-profile data
+trait CredentialBackend {
-/// directory so a private window never inherits the standard
+    fn load(&self, service: &str, account: &str) -> Result<Option<Zeroizing<Vec<u8>>>, String>;
-/// profile's session — same isolation the rest of the runtime
+    fn save(&self, service: &str, account: &str, secret: &[u8]) -> Result<(), String>;
-/// enforces. Writes go through a temp-rename so a partial write
+    fn clear(&self, service: &str, account: &str) -> Result<(), String>;
-/// can't corrupt the persisted token.
+}
+
+struct NativeCredentialBackend;
+
+impl CredentialBackend for NativeCredentialBackend {
+    fn load(&self, service: &str, account: &str) -> Result<Option<Zeroizing<Vec<u8>>>, String> {
+        load_secret(service, account)
+    }
+
+    fn save(&self, service: &str, account: &str, secret: &[u8]) -> Result<(), String> {
+        save_secret(service, account, secret)
+    }
+
+    fn clear(&self, service: &str, account: &str) -> Result<(), String> {
+        clear_secret(service, account)
+    }
+}
+
+/// Profile-scoped native credential store with one-time plaintext-file migration.
 #[derive(Clone, Debug)]
 pub struct BearerTokenStore {
-    path: PathBuf,
+    account: String,
+    lock_path: PathBuf,
+    migration_marker_path: PathBuf,
+    legacy_paths: Vec<PathBuf>,
 }
 
 impl BearerTokenStore {
-    pub fn new(path: PathBuf) -> Self {
+    pub fn new(profile_id: &ProfileId, profile_data_dir: &Path) -> Self {
-        Self { path }
+        let sync_dir = profile_data_dir.join("sync");
+        Self {
+            account: profile_id.as_str().to_string(),
+            lock_path: sync_dir.join("bearer.lock"),
+            migration_marker_path: sync_dir.join("bearer.migrated"),
+            legacy_paths: vec![sync_dir.join("bearer.token")],
+        }
     }
 
-    pub fn path(&self) -> &Path {
+    pub fn with_legacy_path(mut self, path: PathBuf) -> Self {
-        &self.path
+        if !self.legacy_paths.contains(&path) {
+            self.legacy_paths.push(path);
+        }
+        self
     }
 
     pub fn load(&self) -> Result<Option<BearerToken>, SyncClientError> {
-        match fs::read_to_string(&self.path) {
+        self.load_with(&NativeCredentialBackend)
-            Ok(contents) => {
-                if contents.trim().is_empty() {
-                    return Ok(None);
-                }
-                BearerToken::new(contents).map(Some)
-            }
-            Err(error) if error.kind() == ErrorKind::NotFound => Ok(None),
-            Err(error) => Err(SyncClientError::TokenStorage(error.to_string())),
-        }
     }
 
     pub fn save(&self, token: &BearerToken) -> Result<(), SyncClientError> {
-        if let Some(parent) = self.path.parent() {
+        self.save_with(&NativeCredentialBackend, token)
-            fs::create_dir_all(parent).map_err(io_err)?;
-        }
-        let tmp = self.path.with_extension("tmp");
-        fs::write(&tmp, token.as_str()).map_err(io_err)?;
-        fs::rename(&tmp, &self.path).map_err(io_err)?;
-        Ok(())
     }
 
     pub fn clear(&self) -> Result<(), SyncClientError> {
-        remove_file_if_present(&self.path)?;
+        self.clear_with(&NativeCredentialBackend)
-        remove_file_if_present(&self.path.with_extension("tmp"))
+    }
+
+    pub fn clear_if_matches(&self, token: &BearerToken) -> Result<bool, SyncClientError> {
+        self.clear_if_matches_with(&NativeCredentialBackend, token)
+    }
+
+    fn clear_if_matches_with<B: CredentialBackend>(
+        &self,
+        backend: &B,
+        token: &BearerToken,
+    ) -> Result<bool, SyncClientError> {
+        self.with_lock(|| {
+            let current = load_backend_token(backend, &self.account)?;
+            ensure_migration_marker(&self.migration_marker_path)?;
+            self.cleanup_legacy_paths()?;
+            if current.as_ref().is_some_and(|current| current != token) {
+                return Ok(false);
+            }
+            backend.clear(KEYCHAIN_SERVICE, &self.account).map_err(storage_error)?;
+            Ok(true)
+        })
+    }
+
+    pub fn clear_legacy_files(&self) -> Result<(), SyncClientError> {
+        self.with_lock(|| self.cleanup_legacy_paths())
+    }
+
+    fn load_with<B: CredentialBackend>(
+        &self,
+        backend: &B,
+    ) -> Result<Option<BearerToken>, SyncClientError> {
+        self.with_lock(|| self.load_locked(backend))
+    }
+
+    fn save_with<B: CredentialBackend>(
+        &self,
+        backend: &B,
+        token: &BearerToken,
+    ) -> Result<(), SyncClientError> {
+        self.with_lock(|| {
+            ensure_migration_marker(&self.migration_marker_path)?;
+            self.cleanup_legacy_paths()?;
+            backend
+                .save(KEYCHAIN_SERVICE, &self.account, token.as_str().as_bytes())
+                .map_err(storage_error)
+        })
+    }
+
+    fn clear_with<B: CredentialBackend>(&self, backend: &B) -> Result<(), SyncClientError> {
+        self.with_lock(|| {
+            ensure_migration_marker(&self.migration_marker_path)?;
+            self.cleanup_legacy_paths()?;
+            backend.clear(KEYCHAIN_SERVICE, &self.account).map_err(storage_error)
+        })
+    }
+
+    fn load_locked<B: CredentialBackend>(
+        &self,
+        backend: &B,
+    ) -> Result<Option<BearerToken>, SyncClientError> {
+        if let Some(token) = load_backend_token(backend, &self.account)? {
+            ensure_migration_marker(&self.migration_marker_path)?;
+            self.cleanup_legacy_paths()?;
+            return Ok(Some(token));
+        }
+
+        if migration_marker_exists(&self.migration_marker_path)? {
+            self.cleanup_legacy_paths()?;
+            return Ok(None);
+        }
+
+        let mut candidate = None;
+        for path in &self.legacy_paths {
+            if let Some(token) = read_legacy_token(path)? {
+                candidate = Some(token);
+                break;
+            }
+        }
+        let Some(token) = candidate else {
+            self.cleanup_legacy_tmp_files()?;
+            return Ok(None);
+        };
+        backend
+            .save(KEYCHAIN_SERVICE, &self.account, token.as_str().as_bytes())
+            .map_err(storage_error)?;
+        if let Err(error) = verify_backend_token(backend, &self.account, &token) {
+            return Err(rollback_migration(backend, &self.account, error));
+        }
+        if let Err(error) = ensure_migration_marker(&self.migration_marker_path) {
+            if matches!(migration_marker_exists(&self.migration_marker_path), Ok(false)) {
+                return Err(rollback_migration(backend, &self.account, error));
+            }
+            return Err(error);
+        }
+        self.cleanup_legacy_paths()?;
+        Ok(Some(token))
+    }
+
+    fn cleanup_legacy_paths(&self) -> Result<(), SyncClientError> {
+        for path in &self.legacy_paths {
+            remove_file_if_present(path)?;
+            remove_file_if_present(&path.with_extension("tmp"))?;
+        }
+        Ok(())
+    }
+
+    fn cleanup_legacy_tmp_files(&self) -> Result<(), SyncClientError> {
+        for path in &self.legacy_paths {
+            remove_file_if_present(&path.with_extension("tmp"))?;
+        }
+        Ok(())
+    }
+
+    fn with_lock<T>(
+        &self,
+        operation: impl FnOnce() -> Result<T, SyncClientError>,
+    ) -> Result<T, SyncClientError> {
+        let lock = open_lock_file(&self.lock_path)?;
+        lock.lock_exclusive().map_err(|error| storage_error(error.to_string()))?;
+        operation()
     }
 }
 
-fn remove_file_if_present(path: &Path) -> Result<(), SyncClientError> {
+fn load_backend_token<B: CredentialBackend>(
-    match fs::remove_file(path) {
+    backend: &B,
-        Ok(()) => Ok(()),
+    account: &str,
-        Err(error) if error.kind() == ErrorKind::NotFound => Ok(()),
+) -> Result<Option<BearerToken>, SyncClientError> {
-        Err(error) => Err(SyncClientError::TokenStorage(error.to_string())),
+    let Some(secret) = backend.load(KEYCHAIN_SERVICE, account).map_err(storage_error)? else {
+        return Ok(None);
+    };
+    let value =
+        std::str::from_utf8(&secret).map_err(|error| storage_error(error.to_string()))?.to_string();
+    BearerToken::new(value).map(Some)
+}
+
+fn verify_backend_token<B: CredentialBackend>(
+    backend: &B,
+    account: &str,
+    token: &BearerToken,
+) -> Result<(), SyncClientError> {
+    let stored = load_backend_token(backend, account)?;
+    if stored.as_ref() != Some(token) {
+        return Err(storage_error("native credential read-back did not match"));
+    }
+    Ok(())
+}
+
+fn rollback_migration<B: CredentialBackend>(
+    backend: &B,
+    account: &str,
+    cause: SyncClientError,
+) -> SyncClientError {
+    match backend.clear(KEYCHAIN_SERVICE, account) {
+        Ok(()) => cause,
+        Err(rollback_error) => {
+            storage_error(format!("{cause}; native credential rollback failed: {rollback_error}"))
+        }
     }
 }
 
-fn io_err(error: io::Error) -> SyncClientError {
+fn read_legacy_token(path: &Path) -> Result<Option<BearerToken>, SyncClientError> {
-    SyncClientError::TokenStorage(error.to_string())
+    let Some(bytes) = read_legacy_bytes(path, MAX_BEARER_TOKEN_BYTES + 1)? else {
+        return Ok(None);
+    };
+    let value =
+        std::str::from_utf8(&bytes).map_err(|error| storage_error(error.to_string()))?.to_string();
+    BearerToken::new(value).map(Some)
+}
+
+fn storage_error(message: impl Into<String>) -> SyncClientError {
+    SyncClientError::BearerCredentialStorage(message.into())
 }
 
 #[cfg(test)]
-mod tests {
+#[path = "auth_tests.rs"]
-    use super::*;
+mod tests;
-    use std::env::temp_dir;
-
-    #[test]
-    fn rejects_obviously_broken_tokens() {
-        assert!(BearerToken::new("").is_err());
-        assert!(BearerToken::new("   ").is_err());
-        assert!(BearerToken::new("short").is_err());
-        // Spaces are not in the Better Auth bearer charset.
-        assert!(BearerToken::new(format!("{}aaa bb", "a".repeat(40))).is_err());
-    }
-
-    #[test]
-    fn accepts_better_auth_shape() -> Result<(), SyncClientError> {
-        let token = format!("{}-{}_{}", "a".repeat(20), "b".repeat(20), "c".repeat(20));
-        BearerToken::new(token).map(|_| ())
-    }
-
-    #[test]
-    fn token_store_round_trips() -> Result<(), SyncClientError> {
-        let dir = temp_dir().join(format!("ely-token-{}", uuid::Uuid::now_v7().simple()));
-        let store = BearerTokenStore::new(dir.join("token"));
-        let token = BearerToken::new("a".repeat(64))?;
-        assert_eq!(store.load()?, None);
-
-        store.save(&token)?;
-        assert_eq!(store.load()?, Some(token.clone()));
-        fs::write(store.path().with_extension("tmp"), token.as_str()).map_err(io_err)?;
-
-        store.clear()?;
-        assert_eq!(store.load()?, None);
-        assert!(!store.path().with_extension("tmp").exists());
-        Ok(())
-    }
-}

crates/ely_sync_client/src/auth_files.rs

@@ -0,0 +1,296 @@
+use std::{
+    fs,
+    io::{self, ErrorKind, Read, Write},
+    path::{Component, Path, PathBuf},
+};
+
+use cap_fs_ext::{
+    DirExt, FollowSymlinks, MetadataExt as CrossPlatformMetadataExt, OpenOptionsFollowExt,
+};
+use cap_std::{
+    ambient_authority,
+    fs::{Dir, File, OpenOptions, Permissions},
+};
+use zeroize::Zeroizing;
+
+use crate::error::SyncClientError;
+
+const MARKER_CONTENT: &[u8] = b"ely-bearer-migration-v1\n";
+
+pub(super) fn read_legacy_bytes(
+    path: &Path,
+    maximum_bytes: usize,
+) -> Result<Option<Zeroizing<Vec<u8>>>, SyncClientError> {
+    let Some((directory, name)) = open_parent(path, false)? else {
+        return Ok(None);
+    };
+    let Some(file) = open_existing(&directory, name)? else {
+        return Ok(None);
+    };
+    validate_private_file(&file)?;
+    let mut bytes = Zeroizing::new(Vec::new());
+    file.into_std().take((maximum_bytes + 1) as u64).read_to_end(&mut bytes).map_err(storage_io)?;
+    if bytes.len() > maximum_bytes {
+        return Err(storage_error("legacy bearer token is too large"));
+    }
+    Ok(Some(bytes))
+}
+
+pub(super) fn ensure_migration_marker(path: &Path) -> Result<(), SyncClientError> {
+    let (directory, name) = open_parent(path, true)?
+        .ok_or_else(|| storage_error("bearer migration marker parent is missing"))?;
+    if let Some(file) = open_existing(&directory, name)? {
+        return validate_migration_marker(file);
+    }
+    let temporary_path = marker_temporary_path(path)?;
+    remove_file_if_present(&temporary_path)?;
+    let temporary_name = temporary_path
+        .file_name()
+        .ok_or_else(|| storage_error("bearer migration marker temp name is missing"))?;
+    let mut options = private_open_options();
+    options.write(true).create_new(true);
+    let mut file = directory.open_with(temporary_name, &options).map_err(storage_io)?;
+    validate_private_file(&file)?;
+    set_private_file_permissions(&file)?;
+    file.write_all(MARKER_CONTENT).map_err(storage_io)?;
+    file.sync_all().map_err(storage_io)?;
+    drop(file);
+    directory.rename(temporary_name, &directory, name).map_err(storage_io)?;
+    sync_directory(&directory)
+}
+
+pub(super) fn migration_marker_exists(path: &Path) -> Result<bool, SyncClientError> {
+    let Some((directory, name)) = open_parent(path, false)? else {
+        return Ok(false);
+    };
+    let Some(file) = open_existing(&directory, name)? else {
+        return Ok(false);
+    };
+    validate_migration_marker(file)?;
+    Ok(true)
+}
+
+fn validate_migration_marker(file: File) -> Result<(), SyncClientError> {
+    validate_private_file(&file)?;
+    let mut bytes = Vec::new();
+    file.into_std()
+        .take((MARKER_CONTENT.len() + 1) as u64)
+        .read_to_end(&mut bytes)
+        .map_err(storage_io)?;
+    if bytes != MARKER_CONTENT {
+        return Err(storage_error("bearer migration marker content is invalid"));
+    }
+    Ok(())
+}
+
+fn marker_temporary_path(path: &Path) -> Result<PathBuf, SyncClientError> {
+    let mut name = path
+        .file_name()
+        .ok_or_else(|| storage_error("bearer migration marker name is missing"))?
+        .to_os_string();
+    name.push(".tmp");
+    Ok(path.with_file_name(name))
+}
+
+pub(super) fn remove_file_if_present(path: &Path) -> Result<(), SyncClientError> {
+    let Some((directory, name)) = open_parent(path, false)? else {
+        return Ok(());
+    };
+    let metadata = match directory.symlink_metadata(name) {
+        Ok(metadata) => metadata,
+        Err(error) if error.kind() == ErrorKind::NotFound => return Ok(()),
+        Err(error) => return Err(storage_io(error)),
+    };
+    if metadata.is_symlink() {
+        return directory.remove_file_or_symlink(name).map_err(storage_io);
+    }
+    let file = open_existing(&directory, name)?.ok_or_else(|| {
+        storage_error("legacy bearer token disappeared during cleanup validation")
+    })?;
+    validate_private_file(&file)?;
+    drop(file);
+    directory.remove_file_or_symlink(name).map_err(storage_io)
+}
+
+pub(super) fn open_lock_file(path: &Path) -> Result<fs::File, SyncClientError> {
+    let (directory, name) =
+        open_parent(path, true)?.ok_or_else(|| storage_error("bearer lock parent is missing"))?;
+    let mut options = private_open_options();
+    options.read(true).write(true).create(true);
+    let file = directory.open_with(name, &options).map_err(storage_io)?;
+    validate_private_file(&file)?;
+    set_private_file_permissions(&file)?;
+    Ok(file.into_std())
+}
+
+fn open_parent(
+    path: &Path,
+    create: bool,
+) -> Result<Option<(Dir, &std::ffi::OsStr)>, SyncClientError> {
+    let parent = path.parent().ok_or_else(|| storage_error("credential file parent is missing"))?;
+    let name = path.file_name().ok_or_else(|| storage_error("credential file name is missing"))?;
+    let Some(directory) = open_directory_nofollow(parent, create)? else {
+        return Ok(None);
+    };
+    validate_private_directory(&directory)?;
+    set_private_directory_permissions(&directory)?;
+    Ok(Some((directory, name)))
+}
+
+fn open_directory_nofollow(path: &Path, create: bool) -> Result<Option<Dir>, SyncClientError> {
+    let mut root = PathBuf::new();
+    let mut names = Vec::new();
+    for component in path.components() {
+        match component {
+            Component::Prefix(prefix) => root.push(prefix.as_os_str()),
+            Component::RootDir => root.push(std::path::MAIN_SEPARATOR_STR),
+            Component::Normal(name) => names.push(name.to_os_string()),
+            Component::CurDir => {}
+            Component::ParentDir => {
+                return Err(storage_error("credential path traversal is invalid"));
+            }
+        }
+    }
+    if root.as_os_str().is_empty() {
+        return Err(storage_error("credential paths must be absolute"));
+    }
+    let mut directory = Dir::open_ambient_dir(root, ambient_authority()).map_err(storage_io)?;
+    #[cfg(windows)]
+    let strict_component = names.len().saturating_sub(4);
+    #[cfg(windows)]
+    let mut require_nofollow = false;
+    #[cfg(windows)]
+    let mut component_index = 0;
+    #[cfg(not(windows))]
+    let mut require_nofollow = directory_requires_nofollow(&directory)?;
+    for name in names {
+        #[cfg(windows)]
+        {
+            require_nofollow |= component_index >= strict_component;
+            component_index += 1;
+        }
+        if create {
+            match directory.create_dir(&name) {
+                Ok(()) => {}
+                Err(error) if error.kind() == ErrorKind::AlreadyExists => {}
+                Err(error) => return Err(storage_io(error)),
+            }
+        }
+        let opened = match directory.open_dir_nofollow(&name) {
+            Ok(directory) => directory,
+            Err(_) if !require_nofollow => match directory.open_dir(&name) {
+                Ok(directory) => directory,
+                Err(error) if !create && error.kind() == ErrorKind::NotFound => return Ok(None),
+                Err(error) => return Err(storage_io(error)),
+            },
+            Err(error) if !create && error.kind() == ErrorKind::NotFound => return Ok(None),
+            Err(error) => return Err(storage_io(error)),
+        };
+        #[cfg(not(windows))]
+        {
+            require_nofollow |= directory_requires_nofollow(&opened)?;
+        }
+        directory = opened;
+    }
+    Ok(Some(directory))
+}
+
+#[cfg(unix)]
+fn directory_requires_nofollow(directory: &Dir) -> Result<bool, SyncClientError> {
+    use cap_std::fs::MetadataExt;
+
+    let metadata = directory.dir_metadata().map_err(storage_io)?;
+    Ok(metadata.uid() == rustix::process::geteuid().as_raw() || metadata.mode() & 0o022 != 0)
+}
+
+#[cfg(not(any(unix, windows)))]
+fn directory_requires_nofollow(_directory: &Dir) -> Result<bool, SyncClientError> {
+    Ok(true)
+}
+
+fn open_existing(directory: &Dir, name: &std::ffi::OsStr) -> Result<Option<File>, SyncClientError> {
+    let mut options = private_open_options();
+    options.read(true);
+    match directory.open_with(name, &options) {
+        Ok(file) => Ok(Some(file)),
+        Err(error) if error.kind() == ErrorKind::NotFound => Ok(None),
+        Err(error) => Err(storage_io(error)),
+    }
+}
+
+fn private_open_options() -> OpenOptions {
+    let mut options = OpenOptions::new();
+    options.follow(FollowSymlinks::No);
+    #[cfg(unix)]
+    {
+        use cap_std::fs::OpenOptionsExt;
+        options.mode(0o600);
+    }
+    options
+}
+
+fn validate_private_directory(directory: &Dir) -> Result<(), SyncClientError> {
+    let metadata = directory.dir_metadata().map_err(storage_io)?;
+    if !metadata.is_dir() {
+        return Err(storage_error("credential file parent is not a directory"));
+    }
+    #[cfg(unix)]
+    {
+        use cap_std::fs::MetadataExt;
+        if metadata.uid() != rustix::process::geteuid().as_raw() {
+            return Err(storage_error("credential file parent ownership is invalid"));
+        }
+    }
+    Ok(())
+}
+
+fn validate_private_file(file: &File) -> Result<(), SyncClientError> {
+    let metadata = file.metadata().map_err(storage_io)?;
+    if !metadata.is_file() || CrossPlatformMetadataExt::nlink(&metadata) != 1 {
+        return Err(storage_error("credential file link state is invalid"));
+    }
+    #[cfg(unix)]
+    {
+        use cap_std::fs::MetadataExt;
+        if metadata.uid() != rustix::process::geteuid().as_raw() {
+            return Err(storage_error("credential file ownership is invalid"));
+        }
+    }
+    Ok(())
+}
+
+fn set_private_directory_permissions(directory: &Dir) -> Result<(), SyncClientError> {
+    #[cfg(unix)]
+    directory
+        .set_permissions(".", Permissions::from_std(fs::Permissions::from_mode(0o700)))
+        .map_err(storage_io)?;
+    Ok(())
+}
+
+fn set_private_file_permissions(file: &File) -> Result<(), SyncClientError> {
+    #[cfg(unix)]
+    file.set_permissions(Permissions::from_std(fs::Permissions::from_mode(0o600)))
+        .map_err(storage_io)?;
+    Ok(())
+}
+
+#[cfg(unix)]
+fn sync_directory(directory: &Dir) -> Result<(), SyncClientError> {
+    directory.try_clone().map_err(storage_io)?.into_std_file().sync_all().map_err(storage_io)
+}
+
+#[cfg(not(unix))]
+fn sync_directory(_directory: &Dir) -> Result<(), SyncClientError> {
+    Ok(())
+}
+
+#[cfg(unix)]
+use std::os::unix::fs::PermissionsExt;
+
+fn storage_io(error: io::Error) -> SyncClientError {
+    storage_error(error.to_string())
+}
+
+fn storage_error(message: impl Into<String>) -> SyncClientError {
+    SyncClientError::BearerCredentialStorage(message.into())
+}

crates/ely_sync_client/src/auth_tests.rs

@@ -0,0 +1,483 @@
+use std::{
+    collections::BTreeMap,
+    fs,
+    sync::{Mutex, MutexGuard},
+};
+
+use ely_domain::ProfileId;
+use zeroize::Zeroizing;
+
+use super::*;
+
+#[derive(Default)]
+struct MemoryCredentialBackend {
+    values: Mutex<BTreeMap<(String, String), Vec<u8>>>,
+}
+
+impl CredentialBackend for MemoryCredentialBackend {
+    fn load(&self, service: &str, account: &str) -> Result<Option<Zeroizing<Vec<u8>>>, String> {
+        Ok(self
+            .values()
+            .get(&(service.to_string(), account.to_string()))
+            .cloned()
+            .map(Zeroizing::new))
+    }
+
+    fn save(&self, service: &str, account: &str, secret: &[u8]) -> Result<(), String> {
+        self.values().insert((service.to_string(), account.to_string()), secret.to_vec());
+        Ok(())
+    }
+
+    fn clear(&self, service: &str, account: &str) -> Result<(), String> {
+        self.values().remove(&(service.to_string(), account.to_string()));
+        Ok(())
+    }
+}
+
+impl MemoryCredentialBackend {
+    fn values(&self) -> MutexGuard<'_, BTreeMap<(String, String), Vec<u8>>> {
+        self.values.lock().unwrap_or_else(std::sync::PoisonError::into_inner)
+    }
+}
+
+struct DroppingCredentialBackend;
+
+impl CredentialBackend for DroppingCredentialBackend {
+    fn load(&self, _service: &str, _account: &str) -> Result<Option<Zeroizing<Vec<u8>>>, String> {
+        Ok(None)
+    }
+
+    fn save(&self, _service: &str, _account: &str, _secret: &[u8]) -> Result<(), String> {
+        Ok(())
+    }
+
+    fn clear(&self, _service: &str, _account: &str) -> Result<(), String> {
+        Ok(())
+    }
+}
+
+struct SaveFailureBackend;
+
+impl CredentialBackend for SaveFailureBackend {
+    fn load(&self, _service: &str, _account: &str) -> Result<Option<Zeroizing<Vec<u8>>>, String> {
+        Ok(None)
+    }
+
+    fn save(&self, _service: &str, _account: &str, _secret: &[u8]) -> Result<(), String> {
+        Err("credential backend is locked".to_string())
+    }
+
+    fn clear(&self, _service: &str, _account: &str) -> Result<(), String> {
+        Ok(())
+    }
+}
+
+#[derive(Default)]
+struct ClearFailureBackend {
+    values: Mutex<BTreeMap<(String, String), Vec<u8>>>,
+}
+
+impl CredentialBackend for ClearFailureBackend {
+    fn load(&self, service: &str, account: &str) -> Result<Option<Zeroizing<Vec<u8>>>, String> {
+        Ok(self
+            .values
+            .lock()
+            .unwrap_or_else(std::sync::PoisonError::into_inner)
+            .get(&(service.to_string(), account.to_string()))
+            .cloned()
+            .map(Zeroizing::new))
+    }
+
+    fn save(&self, service: &str, account: &str, secret: &[u8]) -> Result<(), String> {
+        self.values
+            .lock()
+            .unwrap_or_else(std::sync::PoisonError::into_inner)
+            .insert((service.to_string(), account.to_string()), secret.to_vec());
+        Ok(())
+    }
+
+    fn clear(&self, _service: &str, _account: &str) -> Result<(), String> {
+        Err("credential backend is locked".to_string())
+    }
+}
+
+#[test]
+fn validates_token_shape_boundaries() -> Result<(), SyncClientError> {
+    assert!(BearerToken::new("").is_err());
+    assert!(BearerToken::new("short").is_err());
+    assert!(BearerToken::new(format!("{}aaa bb", "a".repeat(40))).is_err());
+    BearerToken::new("a".repeat(32))?;
+    BearerToken::new("a".repeat(MAX_BEARER_TOKEN_BYTES))?;
+    assert!(BearerToken::new("a".repeat(MAX_BEARER_TOKEN_BYTES + 1)).is_err());
+    Ok(())
+}
+
+#[test]
+fn debug_output_redacts_the_token() -> Result<(), SyncClientError> {
+    let token = BearerToken::new("secret-session-token".repeat(3))?;
+    let output = format!("{token:?}");
+
+    assert_eq!(output, "BearerToken([REDACTED])");
+    assert!(!output.contains(token.as_str()));
+    Ok(())
+}
+
+#[test]
+fn keychain_entry_wins_and_cleans_every_legacy_path() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    let old = directory.path().join("old/bearer.token");
+    write_token(&stable, 'a')?;
+    write_token(&old, 'b')?;
+    write_token(&stable.with_extension("tmp"), 'c')?;
+    write_token(&old.with_extension("tmp"), 'd')?;
+    let backend = MemoryCredentialBackend::default();
+    let expected = BearerToken::new("e".repeat(64))?;
+    backend.save(KEYCHAIN_SERVICE, profile_id.as_str(), expected.as_str().as_bytes())?;
+    let store = BearerTokenStore::new(&profile_id, directory.path()).with_legacy_path(old.clone());
+
+    assert_eq!(store.load_with(&backend)?, Some(expected));
+    for path in [stable, old] {
+        assert!(!path.exists());
+        assert!(!path.with_extension("tmp").exists());
+    }
+    assert!(migration_marker_path(directory.path()).exists());
+    Ok(())
+}
+
+#[test]
+fn stable_legacy_token_precedes_old_default_source() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    let old = directory.path().join("old/bearer.token");
+    write_token(&stable, 'a')?;
+    write_token(&old, 'b')?;
+    let backend = MemoryCredentialBackend::default();
+    let store = BearerTokenStore::new(&profile_id, directory.path()).with_legacy_path(old.clone());
+
+    assert_eq!(
+        store.load_with(&backend)?.as_ref().map(BearerToken::as_str),
+        Some("a".repeat(64).as_str())
+    );
+    assert!(!stable.exists());
+    assert!(!old.exists());
+    Ok(())
+}
+
+#[test]
+fn failed_keychain_readback_preserves_the_legacy_source() -> Result<(), Box<dyn std::error::Error>>
+{
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    write_token(&stable, 'a')?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+
+    assert!(store.load_with(&DroppingCredentialBackend).is_err());
+    assert!(stable.exists());
+    Ok(())
+}
+
+#[test]
+fn existing_keychain_entry_finishes_a_crashed_migration() -> Result<(), Box<dyn std::error::Error>>
+{
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    write_token(&stable, 'a')?;
+    let backend = MemoryCredentialBackend::default();
+    backend.save(KEYCHAIN_SERVICE, profile_id.as_str(), "a".repeat(64).as_bytes())?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+
+    assert!(store.load_with(&backend)?.is_some());
+    assert!(!stable.exists());
+    Ok(())
+}
+
+#[test]
+fn profile_accounts_are_isolated_and_clear_is_idempotent() -> Result<(), Box<dyn std::error::Error>>
+{
+    let directory = tempfile::tempdir()?;
+    let first_id = ProfileId::new();
+    let second_id = ProfileId::new();
+    let first = BearerTokenStore::new(&first_id, &directory.path().join("first"));
+    let second = BearerTokenStore::new(&second_id, &directory.path().join("second"));
+    let first_token = BearerToken::new("a".repeat(64))?;
+    let second_token = BearerToken::new("b".repeat(64))?;
+    let backend = MemoryCredentialBackend::default();
+
+    first.save_with(&backend, &first_token)?;
+    second.save_with(&backend, &second_token)?;
+    assert_eq!(first.load_with(&backend)?, Some(first_token));
+    assert_eq!(second.load_with(&backend)?, Some(second_token.clone()));
+    first.clear_with(&backend)?;
+    first.clear_with(&backend)?;
+    assert_eq!(first.load_with(&backend)?, None);
+    assert_eq!(second.load_with(&backend)?, Some(second_token));
+    Ok(())
+}
+
+#[test]
+fn conditional_clear_preserves_a_newer_profile_token() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+    let old = BearerToken::new("a".repeat(64))?;
+    let current = BearerToken::new("b".repeat(64))?;
+    let backend = MemoryCredentialBackend::default();
+
+    store.save_with(&backend, &old)?;
+    store.save_with(&backend, &current)?;
+    assert!(!store.clear_if_matches_with(&backend, &old)?);
+    assert_eq!(store.load_with(&backend)?, Some(current.clone()));
+    assert!(store.clear_if_matches_with(&backend, &current)?);
+    assert_eq!(store.load_with(&backend)?, None);
+    Ok(())
+}
+
+#[test]
+fn clear_failure_preserves_the_credential_for_retry() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+    let token = BearerToken::new("a".repeat(64))?;
+    let backend = ClearFailureBackend::default();
+
+    store.save_with(&backend, &token)?;
+    assert!(store.clear_with(&backend).is_err());
+    assert_eq!(store.load_with(&backend)?, Some(token));
+    Ok(())
+}
+
+#[test]
+fn migration_marker_blocks_recreated_legacy_tokens() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let old = directory.path().join("old/bearer.token");
+    let store = BearerTokenStore::new(&profile_id, directory.path()).with_legacy_path(old.clone());
+    let backend = MemoryCredentialBackend::default();
+    let token = BearerToken::new("a".repeat(64))?;
+
+    store.save_with(&backend, &token)?;
+    store.clear_with(&backend)?;
+    write_token(&old, 'b')?;
+
+    assert_eq!(store.load_with(&backend)?, None);
+    assert!(!old.exists());
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn cleanup_failure_prevents_a_direct_keychain_commit() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    let target = directory.path().join("target.tmp");
+    write_token(&target, 'b')?;
+    fs::create_dir_all(stable.parent().ok_or("missing stable parent")?)?;
+    fs::hard_link(&target, stable.with_extension("tmp"))?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+    let backend = MemoryCredentialBackend::default();
+    let token = BearerToken::new("a".repeat(64))?;
+
+    assert!(store.save_with(&backend, &token).is_err());
+    assert!(backend.load(KEYCHAIN_SERVICE, profile_id.as_str())?.is_none());
+    Ok(())
+}
+
+#[test]
+fn direct_save_failure_retires_stale_legacy_credentials() -> Result<(), Box<dyn std::error::Error>>
+{
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    write_token(&stable, 'a')?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+    let token = BearerToken::new("b".repeat(64))?;
+
+    assert!(store.save_with(&SaveFailureBackend, &token).is_err());
+    assert!(!stable.exists());
+    assert!(migration_marker_path(directory.path()).exists());
+    assert_eq!(store.load_with(&MemoryCredentialBackend::default())?, None);
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn migration_cleanup_failure_keeps_the_committed_keychain() -> Result<(), Box<dyn std::error::Error>>
+{
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    let target = directory.path().join("target.tmp");
+    write_token(&stable, 'a')?;
+    write_token(&target, 'b')?;
+    fs::hard_link(&target, stable.with_extension("tmp"))?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+    let backend = MemoryCredentialBackend::default();
+
+    assert!(store.load_with(&backend).is_err());
+    assert!(backend.load(KEYCHAIN_SERVICE, profile_id.as_str())?.is_some());
+    assert!(migration_marker_path(directory.path()).exists());
+    fs::remove_file(stable.with_extension("tmp"))?;
+    assert_eq!(
+        store.load_with(&backend)?.as_ref().map(BearerToken::as_str),
+        Some("a".repeat(64).as_str())
+    );
+    Ok(())
+}
+
+#[test]
+fn invalid_migration_marker_never_retires_a_legacy_token() -> Result<(), Box<dyn std::error::Error>>
+{
+    for marker in [b"".as_slice(), b"partial".as_slice()] {
+        let directory = tempfile::tempdir()?;
+        let profile_id = ProfileId::new();
+        let stable = stable_legacy_path(directory.path());
+        let marker_path = migration_marker_path(directory.path());
+        write_token(&stable, 'a')?;
+        fs::write(&marker_path, marker)?;
+        let store = BearerTokenStore::new(&profile_id, directory.path());
+        let backend = MemoryCredentialBackend::default();
+
+        assert!(store.load_with(&backend).is_err());
+        assert!(stable.exists());
+        assert!(backend.load(KEYCHAIN_SERVICE, profile_id.as_str())?.is_none());
+    }
+    Ok(())
+}
+
+#[test]
+fn crashed_marker_temp_is_replaced_atomically() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let marker = migration_marker_path(directory.path());
+    let marker_tmp = marker.with_file_name("bearer.migrated.tmp");
+    fs::create_dir_all(marker.parent().ok_or("missing marker parent")?)?;
+    fs::write(&marker_tmp, b"partial")?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+
+    store.clear_with(&MemoryCredentialBackend::default())?;
+
+    assert_eq!(fs::read(marker)?, b"ely-bearer-migration-v1\n");
+    assert!(!marker_tmp.exists());
+    Ok(())
+}
+
+#[test]
+fn stale_tmp_is_removed_without_becoming_a_token() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let stable = stable_legacy_path(directory.path());
+    write_token(&stable.with_extension("tmp"), 'a')?;
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+
+    assert_eq!(store.load_with(&MemoryCredentialBackend::default())?, None);
+    assert!(!stable.with_extension("tmp").exists());
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn symlink_and_hardlink_legacy_sources_are_rejected() -> Result<(), Box<dyn std::error::Error>> {
+    use std::os::unix::fs::symlink;
+
+    for hard_link in [false, true] {
+        let directory = tempfile::tempdir()?;
+        let profile_id = ProfileId::new();
+        let target = directory.path().join("target.token");
+        let stable = stable_legacy_path(directory.path());
+        write_token(&target, 'a')?;
+        fs::create_dir_all(stable.parent().ok_or("missing stable parent")?)?;
+        if hard_link {
+            fs::hard_link(&target, &stable)?;
+        } else {
+            symlink(&target, &stable)?;
+        }
+        let backend = MemoryCredentialBackend::default();
+        let store = BearerTokenStore::new(&profile_id, directory.path());
+
+        assert!(store.load_with(&backend).is_err());
+        assert!(backend.load(KEYCHAIN_SERVICE, profile_id.as_str())?.is_none());
+    }
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn symlink_and_hardlink_lock_files_are_rejected() -> Result<(), Box<dyn std::error::Error>> {
+    use std::os::unix::fs::{PermissionsExt, symlink};
+
+    for hard_link in [false, true] {
+        let directory = tempfile::tempdir()?;
+        let profile_id = ProfileId::new();
+        let target = directory.path().join("target.lock");
+        let lock = directory.path().join("sync/bearer.lock");
+        fs::write(&target, b"lock-target")?;
+        fs::set_permissions(&target, fs::Permissions::from_mode(0o644))?;
+        fs::create_dir_all(lock.parent().ok_or("missing lock parent")?)?;
+        if hard_link {
+            fs::hard_link(&target, &lock)?;
+        } else {
+            symlink(&target, &lock)?;
+        }
+        let store = BearerTokenStore::new(&profile_id, directory.path());
+
+        assert!(store.load_with(&MemoryCredentialBackend::default()).is_err());
+        assert_eq!(fs::metadata(&target)?.permissions().mode() & 0o777, 0o644);
+    }
+    Ok(())
+}
+
+#[cfg(unix)]
+#[test]
+fn symlinked_profile_directories_are_rejected() -> Result<(), Box<dyn std::error::Error>> {
+    use std::os::unix::fs::symlink;
+
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let target = directory.path().join("target-profile");
+    let linked_profile = directory.path().join("linked-profile");
+    fs::create_dir_all(&target)?;
+    symlink(&target, &linked_profile)?;
+    let store = BearerTokenStore::new(&profile_id, &linked_profile);
+
+    assert!(store.load_with(&MemoryCredentialBackend::default()).is_err());
+    assert!(!target.join("sync").exists());
+    Ok(())
+}
+
+#[cfg(target_os = "macos")]
+#[test]
+fn native_keychain_round_trip() -> Result<(), Box<dyn std::error::Error>> {
+    let directory = tempfile::tempdir()?;
+    let profile_id = ProfileId::new();
+    let store = BearerTokenStore::new(&profile_id, directory.path());
+    let token = BearerToken::new("n".repeat(64))?;
+    let result = (|| {
+        store.save(&token)?;
+        assert_eq!(store.load()?, Some(token));
+        Ok::<(), SyncClientError>(())
+    })();
+    store.clear()?;
+    result?;
+    Ok(())
+}
+
+fn stable_legacy_path(profile_dir: &std::path::Path) -> std::path::PathBuf {
+    profile_dir.join("sync/bearer.token")
+}
+
+fn migration_marker_path(profile_dir: &std::path::Path) -> std::path::PathBuf {
+    profile_dir.join("sync/bearer.migrated")
+}
+
+fn write_token(path: &std::path::Path, character: char) -> Result<(), std::io::Error> {
+    if let Some(parent) = path.parent() {
+        fs::create_dir_all(parent)?;
+    }
+    fs::write(path, character.to_string().repeat(64))
+}

crates/ely_sync_client/src/credential_store.rs

@@ -1,28 +1,174 @@
-use keyring::{Entry, Error as KeyringError};
+use keyring_core::{CredentialStore, Entry, Error as KeyringError};
+use std::sync::{Arc, Mutex};
 use zeroize::Zeroizing;
 
+static NATIVE_STORE: Mutex<Option<Arc<CredentialStore>>> = Mutex::new(None);
+
 pub(crate) fn load_secret(
     service: &str,
     account: &str,
 ) -> Result<Option<Zeroizing<Vec<u8>>>, String> {
-    match entry(service, account)?.get_secret() {
+    native_operation(service, account, |entry| match entry.get_secret() {
         Ok(secret) => Ok(Some(Zeroizing::new(secret))),
         Err(KeyringError::NoEntry) => Ok(None),
-        Err(error) => Err(error.to_string()),
+        Err(error) => Err(error),
-    }
+    })
 }
 
 pub(crate) fn save_secret(service: &str, account: &str, secret: &[u8]) -> Result<(), String> {
-    entry(service, account)?.set_secret(secret).map_err(|error| error.to_string())
+    native_operation(service, account, |entry| entry.set_secret(secret))
 }
 
 pub(crate) fn clear_secret(service: &str, account: &str) -> Result<(), String> {
-    match entry(service, account)?.delete_credential() {
+    native_operation(service, account, |entry| match entry.delete_credential() {
         Ok(()) | Err(KeyringError::NoEntry) => Ok(()),
-        Err(error) => Err(error.to_string()),
+        Err(error) => Err(error),
+    })
+}
+
+fn native_operation<T>(
+    service: &str,
+    account: &str,
+    operation: impl Fn(&Entry) -> keyring_core::Result<T>,
+) -> Result<T, String> {
+    #[cfg(all(unix, not(any(target_os = "macos", target_os = "ios", target_os = "android"))))]
+    {
+        return retry_once(
+            || entry(service, account).and_then(|entry| operation(&entry)),
+            retryable_store_error,
+            clear_cached_store,
+        )
+        .map_err(|error| error.to_string());
+    }
+    #[cfg(not(all(
+        unix,
+        not(any(target_os = "macos", target_os = "ios", target_os = "android"))
+    )))]
+    {
+        entry(service, account)
+            .and_then(|entry| operation(&entry))
+            .map_err(|error| error.to_string())
     }
 }
 
-fn entry(service: &str, account: &str) -> Result<Entry, String> {
+#[cfg(any(
-    Entry::new(service, account).map_err(|error| error.to_string())
+    test,
+    all(unix, not(any(target_os = "macos", target_os = "ios", target_os = "android")))
+))]
+fn retry_once<T, E>(
+    mut attempt: impl FnMut() -> Result<T, E>,
+    should_retry: impl Fn(&E) -> bool,
+    before_retry: impl FnOnce(),
+) -> Result<T, E> {
+    let first = attempt();
+    if first.as_ref().is_err_and(should_retry) {
+        before_retry();
+        attempt()
+    } else {
+        first
+    }
+}
+
+fn entry(service: &str, account: &str) -> keyring_core::Result<Entry> {
+    let store = {
+        let mut guard = NATIVE_STORE.lock().unwrap_or_else(std::sync::PoisonError::into_inner);
+        if guard.is_none() {
+            *guard = Some(platform_store()?);
+        }
+        guard.as_ref().cloned().ok_or(KeyringError::NoDefaultStore)?
+    };
+    build_entry(store.as_ref(), service, account)
+}
+
+#[cfg(any(
+    test,
+    all(unix, not(any(target_os = "macos", target_os = "ios", target_os = "android")))
+))]
+fn retryable_store_error(error: &KeyringError) -> bool {
+    matches!(
+        error,
+        KeyringError::PlatformFailure(_)
+            | KeyringError::NoStorageAccess(_)
+            | KeyringError::NoDefaultStore
+    )
+}
+
+#[cfg(all(unix, not(any(target_os = "macos", target_os = "ios", target_os = "android"))))]
+fn clear_cached_store() {
+    let mut guard = NATIVE_STORE.lock().unwrap_or_else(std::sync::PoisonError::into_inner);
+    *guard = None;
+}
+
+#[cfg(target_os = "windows")]
+fn build_entry(
+    store: &CredentialStore,
+    service: &str,
+    account: &str,
+) -> keyring_core::Result<Entry> {
+    let modifiers = std::collections::HashMap::from([("persistence", "Local")]);
+    store.build(service, account, Some(&modifiers))
+}
+
+#[cfg(not(target_os = "windows"))]
+fn build_entry(
+    store: &CredentialStore,
+    service: &str,
+    account: &str,
+) -> keyring_core::Result<Entry> {
+    store.build(service, account, None)
+}
+
+#[cfg(target_os = "macos")]
+fn platform_store() -> keyring_core::Result<Arc<CredentialStore>> {
+    apple_native_keyring_store::keychain::Store::new().map(|store| store as Arc<CredentialStore>)
+}
+
+#[cfg(target_os = "windows")]
+fn platform_store() -> keyring_core::Result<Arc<CredentialStore>> {
+    windows_native_keyring_store::Store::new().map(|store| store as Arc<CredentialStore>)
+}
+
+#[cfg(all(unix, not(any(target_os = "macos", target_os = "ios", target_os = "android"))))]
+fn platform_store() -> keyring_core::Result<Arc<CredentialStore>> {
+    zbus_secret_service_keyring_store::Store::new().map(|store| store as Arc<CredentialStore>)
+}
+
+#[cfg(not(any(
+    target_os = "macos",
+    target_os = "windows",
+    all(unix, not(any(target_os = "ios", target_os = "android")))
+)))]
+fn platform_store() -> keyring_core::Result<Arc<CredentialStore>> {
+    Err(KeyringError::NoDefaultStore)
+}
+
+#[cfg(test)]
+mod tests {
+    use super::{KeyringError, retry_once, retryable_store_error};
+    use std::cell::Cell;
+
+    #[test]
+    fn retry_policy_targets_store_connectivity_errors() {
+        assert!(retryable_store_error(&KeyringError::NoDefaultStore));
+        assert!(!retryable_store_error(&KeyringError::NoEntry));
+    }
+
+    #[test]
+    fn retry_evicts_once_and_recreates_the_store_once() {
+        let attempts = Cell::new(0);
+        let evictions = Cell::new(0);
+        let result = retry_once(
+            || {
+                let attempt = attempts.get() + 1;
+                attempts.set(attempt);
+                Err::<(), _>(attempt)
+            },
+            |_| true,
+            || evictions.set(evictions.get() + 1),
+        );
+
+        assert_eq!(result, Err(2));
+        assert_eq!(attempts.get(), 2);
+        assert_eq!(evictions.get(), 1);
+    }
 }

crates/ely_sync_client/src/device.rs

@@ -17,6 +17,7 @@ use crate::{
 
 const PUBLIC_KEY_BYTES: usize = 32;
 const MAX_DEVICE_TEXT_CHARS: usize = 128;
+const MAX_STORED_IDENTITY_BYTES: usize = 16 * 1024;
 
 /// Public device identity persisted in the profile directory. Both private
 /// keys live in the macOS data-protection Keychain under `device_id`.
@@ -33,6 +34,18 @@ pub struct DeviceIdentity {
 }
 
 impl DeviceIdentity {
+    pub fn validate_stored_bytes(bytes: &[u8], path: &Path) -> Result<(), SyncClientError> {
+        if bytes.len() > MAX_STORED_IDENTITY_BYTES {
+            return Err(key_error("stored device identity is too large"));
+        }
+        let contents = std::str::from_utf8(bytes)
+            .map_err(|error| SyncClientError::TokenStorage(error.to_string()))?;
+        match decode_stored_identity(contents, path)? {
+            StoredIdentity::V2(identity) => identity.validate(),
+            StoredIdentity::Legacy(identity) => identity.validate(),
+        }
+    }
+
     /// Loads a v2 identity and its Keychain secrets. A legacy public-only
     /// identity is rotated to a fresh device ID because its private key was
     /// never persisted and cannot prove device continuity.
@@ -413,6 +426,31 @@ mod tests {
         Ok(())
     }
 
+    #[test]
+    fn stored_identity_validation_is_bounded_and_schema_strict() -> Result<(), SyncClientError> {
+        let (identity, _) = generate_key_material("Test".to_string(), "macos".to_string())?;
+        let bytes = serde_json::to_vec(&identity).map_err(|error| {
+            SyncClientError::TokenStorage(format!("device identity serialize: {error}"))
+        })?;
+
+        DeviceIdentity::validate_stored_bytes(&bytes, Path::new("device.json"))?;
+        assert!(
+            DeviceIdentity::validate_stored_bytes(
+                &vec![b'a'; MAX_STORED_IDENTITY_BYTES + 1],
+                Path::new("device.json"),
+            )
+            .is_err()
+        );
+        assert!(
+            DeviceIdentity::validate_stored_bytes(
+                br#"{"device_id":"ely-test","unknown":true}"#,
+                Path::new("device.json"),
+            )
+            .is_err()
+        );
+        Ok(())
+    }
+
     #[cfg(target_os = "macos")]
     #[test]
     fn legacy_identity_rotates_to_new_device_id() -> Result<(), SyncClientError> {

crates/ely_sync_client/src/email_otp.rs

@@ -16,6 +16,7 @@
 use serde::{Deserialize, Serialize};
 use std::time::Duration;
 use ureq::{Agent, AgentBuilder};
+use zeroize::Zeroizing;
 
 use crate::{auth::BearerToken, client::ApiClientConfig, error::SyncClientError};
 
@@ -86,20 +87,21 @@ pub fn verify_email_otp(
     match response {
         Ok(ok) => {
             let cookie_token = better_auth_cookie_token(ok.header("set-cookie"));
-            let body = ok.into_string().map_err(|error| SyncClientError::HttpStatus {
+            let body =
+                Zeroizing::new(ok.into_string().map_err(|error| SyncClientError::HttpStatus {
                     endpoint: endpoint.clone(),
                     status: 200,
                     body: error.to_string(),
-            })?;
+                })?);
             let json = serde_json::from_str::<VerifyOtpResponse>(&body).map_err(|error| {
                 SyncClientError::Json { endpoint: endpoint.clone(), source: error }
             })?;
-            let token = json.token.or(cookie_token).ok_or_else(|| {
+            let token = json.token.map(Zeroizing::new).or(cookie_token).ok_or_else(|| {
                 SyncClientError::TokenStorage(
                     "sign-in response did not include a session token".to_string(),
                 )
             })?;
-            BearerToken::new(token)
+            BearerToken::new(token.as_str())
         }
         Err(ureq::Error::Status(status, raw)) => {
             let body = raw.into_string().unwrap_or_default();
@@ -117,14 +119,14 @@ fn build_agent() -> Agent {
 /// better-auth.session_token=<token>; …` header. Strip the cookie's
 /// attributes and return just the value. Multi-cookie responses are
 /// concatenated by `ureq` into a single header line per spec.
-fn better_auth_cookie_token(set_cookie: Option<&str>) -> Option<String> {
+fn better_auth_cookie_token(set_cookie: Option<&str>) -> Option<Zeroizing<String>> {
     let header = set_cookie?;
     for cookie in header.split(',') {
         let trimmed = cookie.trim();
         if let Some(rest) = trimmed.strip_prefix("better-auth.session_token=") {
             let token = rest.split(';').next()?.trim();
             if !token.is_empty() {
-                return Some(token.to_string());
+                return Some(Zeroizing::new(token.to_string()));
             }
         }
     }
@@ -139,7 +141,10 @@ mod tests {
     fn picks_session_token_out_of_set_cookie_header() {
         let header =
             "better-auth.session_token=abc.def.ghi; Path=/; HttpOnly; Secure; SameSite=Lax";
-        assert_eq!(better_auth_cookie_token(Some(header)), Some("abc.def.ghi".to_string()),);
+        assert_eq!(
+            better_auth_cookie_token(Some(header)).as_deref().map(String::as_str),
+            Some("abc.def.ghi"),
+        );
     }
 
     #[test]

crates/ely_sync_client/src/error.rs

@@ -8,6 +8,9 @@ pub enum SyncClientError {
     #[error("Bearer token storage is unavailable: {0}")]
     TokenStorage(String),
 
+    #[error("Bearer credential storage is unavailable: {0}")]
+    BearerCredentialStorage(String),
+
     #[error("HTTP request failed for {endpoint}: {source}")]
     Http {
         endpoint: String,

crates/ely_sync_client/src/lib.rs

@@ -17,6 +17,7 @@
 //!   the bearer token out-of-band and hand it to the client.
 
 pub mod auth;
+mod auth_files;
 pub mod client;
 mod credential_store;
 pub mod device;