diff --git a/src/main/agent-runtime/internal-tools/file-approval-handler.ts b/src/main/agent-runtime/internal-tools/file-approval-handler.ts
new file mode 100644
index 00000000..e32d9427
--- /dev/null
+++ b/src/main/agent-runtime/internal-tools/file-approval-handler.ts
@@ -0,0 +1,171 @@
+/**
+ * Main-side handler for the `file_approval` internal tool (C4 part 2/5).
+ *
+ * Mirrors the control flow of `POST /api/companies/:id/approvals` in
+ * `api-server/routes-approvals.ts`: validate → enforce the
+ * `approve_ceo_strategy` ordering gate → request approval → auto-
+ * approve or notify. Both the tool path and the HTTP path funnel
+ * through the same `db.approvalsMod.requestApproval` + `shouldAutoApprove`
+ * plumbing, so the board sees identical rows regardless of entry point.
+ *
+ * No fallbacks: malformed input throws UserInputError, DB failures
+ * throw UpstreamError. The worker tool wrapper surfaces the classified
+ * message as a pi tool-error so the model can correct its call.
+ */
+
+import type { AppDatabase } from "@main/database";
+import { approvalInputSchema } from "@shared/contracts";
+import { resolveApprovalDecision } from "@main/approval-policy";
+import { shouldAutoApprove } from "@main/execution-policy";
+import { UserInputError, UpstreamError, classifyUnknownError } from "@main/errors";
+import type { InvokeInternalToolRpcResult } from "@main/worker/runtime/internal-tools/internal-tool-rpc";
+
+export interface FileApprovalHandlerDeps {
+  db: AppDatabase;
+  onApprovalCreated: (approvalId: string, companyId: string, taskId: string | null, approvalType: string, summary: string) => void;
+  onApprovalResolved: (approvalId: string, companyId: string, decision: string) => void;
+  onDomainChanged: () => void;
+  logger: {
+    info: (...args: unknown[]) => void;
+    warn: (...args: unknown[]) => void;
+    error: (...args: unknown[]) => void;
+  };
+}
+
+export interface FileApprovalHandlerContext {
+  companyId: string;
+  agentId: string;
+}
+
+export function handleFileApprovalToolCall(
+  deps: FileApprovalHandlerDeps,
+  ctx: FileApprovalHandlerContext,
+  rawArgs: unknown,
+): InvokeInternalToolRpcResult {
+  const { db } = deps;
+  const { companyId, agentId: requesterId } = ctx;
+
+  const argObject = typeof rawArgs === "object" && rawArgs !== null
+    ? (rawArgs as Record<string, unknown>)
+    : {};
+
+  const parsed = approvalInputSchema.safeParse({
+    companyId,
+    ...argObject,
+    requestedByAgentId: requesterId,
+  });
+  if (!parsed.success) {
+    throw new UserInputError({
+      code: "file_approval.input.invalid",
+      message: `Invalid file_approval payload: ${parsed.error.issues
+        .map((i) => `${i.path.join(".")}: ${i.message}`)
+        .join("; ")}`,
+      context: { companyId, requesterId },
+    });
+  }
+  const input = parsed.data;
+
+  // Mirror the HTTP route's `approve_ceo_strategy` ordering gate: the
+  // strategy approval cannot exist before any hire_agent approvals do,
+  // and cannot be re-filed once it exists. The tool path would
+  // otherwise re-open the exact loop the HTTP gate was written to
+  // close.
+  if (input.type === "approve_ceo_strategy") {
+    const companyHireApprovals = db.approvalsMod.listCompanyApprovalsByType(companyId, "hire_agent");
+    if (companyHireApprovals.length === 0) {
+      throw new UserInputError({
+        code: "file_approval.strategy.before_hires",
+        message:
+          "approve_ceo_strategy requires at least one hire_agent approval to exist first. File the intended hires, then the strategy.",
+      });
+    }
+    const existingStrategy = db.approvalsMod
+      .listCompanyApprovalsByType(companyId, "approve_ceo_strategy")
+      .find((a) => a.state === "pending" || a.state === "approved");
+    if (existingStrategy) {
+      throw new UserInputError({
+        code: "file_approval.strategy.already_filed",
+        message: `approve_ceo_strategy already exists for this company (id ${existingStrategy.id}); do not submit another.`,
+      });
+    }
+  }
+
+  let approvalId: string;
+  try {
+    approvalId = db.approvalsMod.requestApproval({
+      companyId,
+      type: input.type,
+      relatedTaskId: input.relatedTaskId ?? null,
+      requestedByAgentId: requesterId,
+      relatedAgentId: input.relatedAgentId ?? null,
+      payloadSummary: input.payloadSummary,
+      impactSummary: input.impactSummary,
+      payloadJson: input.payloadJson ?? null,
+    });
+  } catch (error) {
+    throw classifyUnknownError(error, {
+      kind: "upstream",
+      code: "file_approval.create.failed",
+      message: error instanceof Error ? error.message : "Approval could not be created.",
+      context: { companyId, requesterId, type: input.type },
+    });
+  }
+
+  try {
+    db.activityMod.addActivity({
+      companyId,
+      actor: requesterId,
+      action: "approval.created",
+      entityType: "approval",
+      entityId: approvalId,
+      detail: input.payloadSummary,
+    });
+  } catch (error) {
+    throw new UpstreamError({
+      code: "file_approval.activity.failed",
+      message: "Failed to record activity for approval.",
+      cause: error,
+    });
+  }
+
+  deps.onApprovalCreated(
+    approvalId,
+    companyId,
+    input.relatedTaskId ?? null,
+    input.type,
+    input.payloadSummary ?? "",
+  );
+
+  let autoApproved = false;
+  if (shouldAutoApprove(db, companyId, input.type)) {
+    resolveApprovalDecision({
+      db,
+      handleApprovalResolved: deps.onApprovalResolved,
+      companyId,
+      approvalId,
+      state: "approved",
+      decisionNote: "Auto-approved by company policy",
+      detail: "Auto-approved by company policy",
+    });
+    autoApproved = true;
+    deps.logger.info(
+      `[file-approval-handler] Auto-approved approval ${approvalId}: ${input.payloadSummary}`,
+    );
+  }
+
+  deps.onDomainChanged();
+
+  const summary = autoApproved
+    ? `Filed ${input.type} approval ${approvalId}. Auto-approved by company policy.`
+    : `Filed ${input.type} approval ${approvalId}. Pending board decision.`;
+
+  return {
+    content: [{ type: "text", text: summary }],
+    details: {
+      approvalId,
+      autoApproved,
+      type: input.type,
+    },
+    isError: false,
+  };
+}
diff --git a/src/main/worker/runtime/internal-tools/file-approval-tool.ts b/src/main/worker/runtime/internal-tools/file-approval-tool.ts
new file mode 100644
index 00000000..f19f996c
--- /dev/null
+++ b/src/main/worker/runtime/internal-tools/file-approval-tool.ts
@@ -0,0 +1,127 @@
+/**
+ * `file_approval` internal tool (C4 part 2/5).
+ *
+ * Collapses the `bash + node -e + fetch POST /api/companies/:id/approvals`
+ * chain into a single tool-call the CEO (or any agent with request
+ * authority) can invoke directly. The handler in main reuses the same
+ * `db.approvalsMod.requestApproval` primitive and auto-approval policy
+ * the HTTP route uses, so both paths produce identical rows and the
+ * `approve_ceo_strategy` ordering gate fires identically.
+ *
+ * Like `hire_agent`, the worker-side `execute` is a thin RPC proxy.
+ * Validation failures come back as classified errors from main; pi's
+ * tool-error convention surfaces them to the model on the next turn.
+ */
+
+import type { AgentTool } from "@mariozechner/pi-agent-core";
+import { Type, type Static } from "@mariozechner/pi-ai";
+import type { WorkerRpcClient } from "../../entry/rpc";
+import type {
+  InvokeInternalToolRpcPayload,
+  InvokeInternalToolRpcResult,
+} from "./internal-tool-rpc";
+
+export const FILE_APPROVAL_TOOL_NAME = "file_approval";
+
+/**
+ * TypeBox schema for `file_approval` arguments.
+ *
+ * Kept intentionally narrow (type + summaries + optional payload JSON)
+ * so the model sees the shape of an approval as a primitive concept
+ * rather than an HTTP body to marshal. `type` is an enum drawn directly
+ * from `shared/contracts/schemas-approvals.ts :: approvalInputSchema`;
+ * the handler re-validates with zod so adding a new approval type over
+ * there does not silently un-gate here.
+ */
+export const fileApprovalSchema = Type.Object({
+  type: Type.Union(
+    [
+      Type.Literal("hire_agent"),
+      Type.Literal("approve_ceo_strategy"),
+      Type.Literal("dangerous_command"),
+      Type.Literal("secret_access"),
+      Type.Literal("budget_request"),
+      Type.Literal("promotion"),
+      Type.Literal("termination"),
+      Type.Literal("vendor_approval"),
+      Type.Literal("document_review"),
+      Type.Literal("production_deploy"),
+      Type.Literal("incident_escalation"),
+      Type.Literal("social_post"),
+      Type.Literal("deliverable_review"),
+      Type.Literal("budget_override"),
+      Type.Literal("plan_review"),
+      Type.Literal("scope_review"),
+      Type.Literal("draft_review"),
+      Type.Literal("strategy_review"),
+      Type.Literal("exception_review"),
+    ],
+    {
+      description:
+        "Approval type. Use 'approve_ceo_strategy' after filing the initial hire_agent approvals to lock in the org shape.",
+    },
+  ),
+  payloadSummary: Type.String({
+    description:
+      "One-line human-readable summary of what is being approved (≤280 chars).",
+    minLength: 2,
+    maxLength: 280,
+  }),
+  impactSummary: Type.String({
+    description:
+      "Why this approval matters / business rationale (≤400 chars).",
+    minLength: 2,
+    maxLength: 400,
+  }),
+  payloadJson: Type.Optional(
+    Type.String({
+      description:
+        "Optional JSON string carrying structured approval payload. Must be valid JSON if provided.",
+    }),
+  ),
+  relatedTaskId: Type.Optional(
+    Type.String({
+      description: "UUID of the task this approval pertains to, if any.",
+    }),
+  ),
+  relatedAgentId: Type.Optional(
+    Type.String({
+      description: "UUID of the agent this approval pertains to, if any.",
+    }),
+  ),
+});
+
+export type FileApprovalToolInput = Static<typeof fileApprovalSchema>;
+
+/**
+ * Construct the worker-side `file_approval` tool.
+ *
+ * Routes every call through the internal-tool RPC method so main owns
+ * the approval creation + auto-approval policy.
+ */
+export function createFileApprovalTool(rpc: WorkerRpcClient, runId: string): AgentTool<typeof fileApprovalSchema> {
+  return {
+    name: FILE_APPROVAL_TOOL_NAME,
+    label: "file approval",
+    description:
+      "File an approval request with the company board. Use for 'approve_ceo_strategy' after filing initial hires, or for any other decision that requires board sign-off. The request is auto-approved when the company is in hands-off mode; otherwise it waits for the human operator.",
+    parameters: fileApprovalSchema,
+    async execute(toolCallId, params, _signal?, _onUpdate?) {
+      const payload: InvokeInternalToolRpcPayload = {
+        toolName: FILE_APPROVAL_TOOL_NAME,
+        toolCallId,
+        args: params,
+      };
+      const response = await rpc.invoke(runId, "invokeInternalTool", payload);
+      if (!response.ok) {
+        throw new Error(response.error);
+      }
+      const result = response.result as InvokeInternalToolRpcResult;
+      return {
+        content: result.content,
+        details: result.details,
+        isError: result.isError,
+      };
+    },
+  };
+}