diff --git a/src/main/agent-runtime/runtime-bridge.ts b/src/main/agent-runtime/runtime-bridge.ts
index 169d3f3a..ac9f2299 100644
--- a/src/main/agent-runtime/runtime-bridge.ts
+++ b/src/main/agent-runtime/runtime-bridge.ts
@@ -5,6 +5,8 @@ import { ensureTaskThread } from "@main/thread-integration/thread-helpers";
 import { SqliteSessionStore } from "./sqlite-session-store";
 import { HumanApprovalHook } from "./approval-hook";
 import { CostWriter } from "./cost-writer";
+import type { CredentialResolver } from "@main/credentials";
+import { getConnectorDefinition } from "@main/connectors";
 
 export interface RuntimeBridgeDeps {
   db: AppDatabase;
@@ -14,6 +16,7 @@ export interface RuntimeBridgeDeps {
     warn: (...args: unknown[]) => void;
     error: (...args: unknown[]) => void;
   };
+  credentialResolver: CredentialResolver;
 }
 
 interface ActiveRunContext {
@@ -155,7 +158,7 @@ export class RuntimeBridge {
   /** Handles RPC requests issued by the worker (`rpc-request` envelope). */
   async handleRpc(request: {
     rpcId: string;
-    method: "beforeToolCall" | "afterToolCall" | "persistMessage";
+    method: "beforeToolCall" | "afterToolCall" | "persistMessage" | "prepareRun";
     runId: string;
     payload: unknown;
   }): Promise<{ ok: true; result: unknown } | { ok: false; error: string }> {
@@ -184,6 +187,37 @@ export class RuntimeBridge {
         this.getOrCreateStore(payload.taskSessionId).appendMessage(payload.message);
         return { ok: true, result: undefined };
       }
+      if (request.method === "prepareRun") {
+        const payload = request.payload as {
+          connectorId: string;
+          taskSessionId: string;
+          agentId: string;
+          companyId: string;
+          taskId: string | null;
+          modelId: string;
+        };
+        this.registerActiveRun({
+          runId: request.runId,
+          agentId: payload.agentId,
+          companyId: payload.companyId,
+          taskId: payload.taskId,
+          connectorId: payload.connectorId,
+          modelId: payload.modelId,
+          taskSessionId: payload.taskSessionId,
+        });
+        const definition = getConnectorDefinition(payload.connectorId);
+        const resolved = await this.deps.credentialResolver.resolve(payload.connectorId);
+        const priorMessages = this.getOrCreateStore(payload.taskSessionId).loadMessages();
+        return {
+          ok: true,
+          result: {
+            provider: definition.provider,
+            apiKey: resolved.apiKey,
+            extraEnv: resolved.extraEnv ?? {},
+            priorMessages,
+          },
+        };
+      }
       return { ok: false, error: `Unknown RPC method: ${(request as { method: string }).method}` };
     } catch (error) {
       return { ok: false, error: error instanceof Error ? error.message : String(error) };
diff --git a/src/main/orchestration/turn-context.ts b/src/main/orchestration/turn-context.ts
index 30a87293..783ae3f8 100644
--- a/src/main/orchestration/turn-context.ts
+++ b/src/main/orchestration/turn-context.ts
@@ -133,18 +133,25 @@ function resolveSession(
   deps: Pick<TurnContextDeps, "evaluatePreRunSessionRotation" | "logger">,
 ) {
   const activeSession = db.getActiveTaskSession(task.id);
-  let taskSession = activeSession
+  let taskSession: {
+    id: string | null;
+    sessionParams: Record<string, unknown> | null;
+    sessionDisplayId: string | null;
+  } = activeSession
     ? {
-        sessionParams: activeSession.sessionParamsJson ? JSON.parse(activeSession.sessionParamsJson) as Record<string, unknown> : null,
+        id: activeSession.id,
+        sessionParams: activeSession.sessionParamsJson
+          ? (JSON.parse(activeSession.sessionParamsJson) as Record<string, unknown>)
+          : null,
         sessionDisplayId: activeSession.sessionDisplayId,
       }
-    : db.getTaskSession(task.id);
+    : { id: null, ...db.getTaskSession(task.id) };
 
   let finalHandoff = sessionHandoff;
   if (deps.evaluatePreRunSessionRotation && activeSession) {
     const rotationResult = deps.evaluatePreRunSessionRotation(task.id, connectorId);
     if (rotationResult.rotated) {
-      taskSession = { sessionParams: null, sessionDisplayId: null };
+      taskSession = { id: null, sessionParams: null, sessionDisplayId: null };
       if (!finalHandoff && rotationResult.handoff) {
         finalHandoff = rotationResult.handoff;
       }
@@ -220,7 +227,7 @@ function buildConnectorCatalog(
 ) {
   return connectors
     .filter((c) => c.status === "ready")
-    .filter((c) => c.id.startsWith("claude_compat") || db.hasModelPoolSettings(c.id))
+    .filter((c) => db.hasModelPoolSettings(c.id))
     .map((c) => ({
       id: c.id,
       label: c.label,
@@ -336,5 +343,7 @@ export function buildRunPayload(params: RunDispatchParams, deps: TurnContextDeps
     systemPrompt,
     trigger,
     managedSkills: skills.map((s) => ({ runtimeName: s.runtimeName, sourcePath: s.sourcePath })),
+    taskSessionId: taskSession.id ?? runId,
+    executionMode: db.getCompanyExecutionMode(companyId) as "ai_ceo" | "ai_cofounder",
   };
 }
diff --git a/src/main/orchestration/types.ts b/src/main/orchestration/types.ts
index 577fc52b..e08995bd 100644
--- a/src/main/orchestration/types.ts
+++ b/src/main/orchestration/types.ts
@@ -44,6 +44,10 @@ export interface EnqueueRunPayload {
   systemPrompt: string | null;
   trigger: string | null;
   managedSkills: Array<{ runtimeName: string; sourcePath: string }>;
+  /** Task session id used by SqliteSessionStore to load/append messages. */
+  taskSessionId: string;
+  /** Execution mode from the owning company. */
+  executionMode: "ai_ceo" | "ai_cofounder";
 }
 
 export interface OrchestrationDependencies {
diff --git a/src/main/service-graph.ts b/src/main/service-graph.ts
index a9f249b1..104c1692 100644
--- a/src/main/service-graph.ts
+++ b/src/main/service-graph.ts
@@ -14,6 +14,7 @@ import { createWorkerService } from "./worker-service";
 import { createAppLifecycleService } from "./app-lifecycle-service";
 import { createBudgetEnforcementService } from "./budget-enforcement-service";
 import { createSessionManagementService } from "./session-management-service";
+import { createPiRuntimeServices, type PiRuntimeServices } from "./service-graph-pi-runtime";
 import type { DesktopEvent, RunRecord } from "@shared/types";
 import type { AutomationEventContext } from "./automation-service";
 import type { NotificationOptions } from "./notification-service";
@@ -82,6 +83,7 @@ export function createServiceGraph({
   let skillService: ReturnType<typeof createSkillService> | null = null;
   let budgetEnforcementService: ReturnType<typeof createBudgetEnforcementService> | null = null;
   let sessionManagementService: ReturnType<typeof createSessionManagementService> | null = null;
+  const piRuntimeRef: { current: PiRuntimeServices | null } = { current: null };
 
   function getOrCreateSkillService() {
     if (!skillService) throw new Error("Skill service is not initialized.");
@@ -184,10 +186,22 @@ export function createServiceGraph({
     });
     desktopShellService.initialize();
 
+    piRuntimeRef.current = createPiRuntimeServices({
+      db,
+      emitEvent,
+      logger,
+      refreshConnectorHealth: async (connectorId: string) => {
+        if (connectorHealthService) {
+          await connectorHealthService.checkConnector(connectorId as never);
+        }
+      },
+    });
+
     connectorHealthService = createConnectorHealthService({
       db,
       logger,
       publishDomainChanged,
+      credentialStore: piRuntimeRef.current.credentialStore,
     });
 
     workerService = createWorkerService({
@@ -205,6 +219,7 @@ export function createServiceGraph({
       notify,
       budgetService: getOrCreateBudgetEnforcementService(),
       sessionService: getOrCreateSessionManagementService(),
+      getRuntimeBridge: () => piRuntimeRef.current?.runtimeBridge ?? null,
     });
 
     orchestrationService = createOrchestrationService({
@@ -324,6 +339,8 @@ export function createServiceGraph({
         skillService = null;
         budgetEnforcementService = null;
         sessionManagementService = null;
+        piRuntimeRef.current?.release();
+        piRuntimeRef.current = null;
         db.close();
         // Force exit after grace period — covers all platforms (macOS Dock, Windows tray, Linux)
         // Worker child processes (claude/codex CLI) may keep the event loop alive indefinitely
@@ -346,5 +363,6 @@ export function createServiceGraph({
     getOrCreateSkillService,
     getOrCreateBudgetEnforcementService,
     getOrCreateSessionManagementService,
+    getPiRuntime: () => piRuntimeRef.current,
   };
 }
diff --git a/src/main/session-management-service.ts b/src/main/session-management-service.ts
index 7790c6b4..fe80ddb5 100644
--- a/src/main/session-management-service.ts
+++ b/src/main/session-management-service.ts
@@ -1,6 +1,5 @@
 import type { AppDatabase } from "./database";
-import { getConnectorDefinition } from "./connectors";
-import type { ConnectorId, TaskSessionRecord } from "@shared/types";
+import type { TaskSessionRecord } from "@shared/types";
 
 interface SessionManagementDependencies {
   db: AppDatabase;
@@ -38,20 +37,11 @@ export function createSessionManagementService({ db, logger }: SessionManagement
   // company-level overrides; omitted fields fall back to DEFAULT_THRESHOLDS.
   function evaluateRotation(
     session: TaskSessionRecord,
-    connectorId: string,
+    _connectorId: string,
     thresholdsOverride?: RotationThresholds,
   ): { shouldRotate: boolean; reason: string | null } {
-    // D-04: Check adapter exemption
-    try {
-      const connector = getConnectorDefinition(connectorId as ConnectorId);
-      if (connector.module.nativeContextManagement === true) {
-        return { shouldRotate: false, reason: null };
-      }
-    } catch {
-      // Unknown connector - proceed with rotation check
-    }
-
-    // Merge overrides with defaults (per D-01 configurability)
+    // Pi-mono delegates context management to pi-agent-core compaction hooks;
+    // AgentCompany always applies its own rotation thresholds.
     const thresholds = { ...DEFAULT_THRESHOLDS, ...thresholdsOverride };
 
     // D-01: Any-of thresholds - first trigger wins