diff --git a/src/main/orchestration/run-dispatch.ts b/src/main/orchestration/run-dispatch.ts
index fe558ca7..9baa9681 100644
--- a/src/main/orchestration/run-dispatch.ts
+++ b/src/main/orchestration/run-dispatch.ts
@@ -4,6 +4,7 @@ import type { OrchestrationDependencies } from "./types";
 import { buildRunPayload, type RunDispatchParams } from "./turn-context";
 import { validateConnectorModelSelection } from "../connector-model-policy";
 import { resolveWorkspaceWithLockMode } from "./resolve-workspace";
+import { AppError } from "../errors/index.js";
 
 type ResolveWorkspaceTaskInput =
   | (Pick<TaskRecord, "workspaceId" | "projectId"> & { requiresFilesystem?: boolean })
@@ -24,6 +25,7 @@ export function createRunDispatch(deps: OrchestrationDependencies) {
   const {
     db,
     logger,
+    emitEvent,
     isQuitting,
     hasWorkerReady,
     getApiPort,
@@ -38,6 +40,47 @@ export function createRunDispatch(deps: OrchestrationDependencies) {
   const resolveWorkspace: ResolveWorkspaceFn = (task, agent, companyId) =>
     resolveWorkspaceWithLockMode(db, task, agent, companyId);
 
+  function formatDispatchError(error: unknown): string {
+    if (error instanceof AppError) {
+      return `[${error.code}] ${error.message}`;
+    }
+    if (error instanceof Error) {
+      return error.message;
+    }
+    return String(error);
+  }
+
+  function failRunBeforeWorkerEnqueue(
+    params: RunDispatchParams,
+    error: unknown,
+    workspaceLockClaimed: boolean,
+  ): void {
+    const errorMessage = formatDispatchError(error);
+    logger.error(`[run] Dispatch failed before worker enqueue for ${params.runId}: ${errorMessage}`);
+    db.runs.finishRun({
+      runId: params.runId,
+      status: "failed",
+      summary: "Run failed before worker enqueue.",
+      errorMessage,
+      exitCode: null,
+      signal: null,
+      model: params.resolvedModel ?? null,
+      unattributedCost: true,
+    });
+    if (workspaceLockClaimed && params.workspaceMode === "exclusive" && params.workspace) {
+      db.workspacesMod.releaseWorkspaceLock(params.workspace.id, params.runId);
+    }
+    db.activityMod.addActivity({
+      companyId: params.companyId,
+      actor: params.agent.id,
+      action: "run.failed",
+      entityType: "run",
+      entityId: params.runId,
+      detail: errorMessage,
+    });
+    emitEvent({ type: "run-updated", runId: params.runId, action: "completed" });
+  }
+
   function getRunEligibilityFailure(
     agent: { status: string; budgetMonthlyUsd: number; spentMonthlyUsd: number; name: string; connectorId: string; id: string; companyId: string; model?: string | null },
     connector: Pick<ConnectorRecord, "id" | "label" | "status" | "capabilityMatrix">,
@@ -74,57 +117,62 @@ export function createRunDispatch(deps: OrchestrationDependencies) {
   }
 
   function dispatchRunToWorker(params: RunDispatchParams) {
-    if (isQuitting()) {
-      throw new Error("Application is shutting down — refusing to dispatch new run.");
-    }
-    if (!hasWorkerReady()) {
-      throw new Error("Orchestration worker is not ready.");
-    }
-    const connectorIssue = getConnectorExecutionReadinessIssue(params.connector);
-    if (connectorIssue) {
-      throw new Error(connectorIssue);
-    }
+    let workspaceLockClaimed = false;
+    try {
+      if (isQuitting()) {
+        throw new Error("Application is shutting down — refusing to dispatch new run.");
+      }
+      if (!hasWorkerReady()) {
+        throw new Error("Orchestration worker is not ready.");
+      }
+      const connectorIssue = getConnectorExecutionReadinessIssue(params.connector);
+      if (connectorIssue) {
+        throw new Error(connectorIssue);
+      }
 
-    // D-02: Claim the workspace lock synchronously before enqueuing the run.
-    // Previously the worker claimed the lock only after it emitted `running`,
-    // so two runs could race between enqueue and startup and both read the
-    // same workspace mid-write. Main is the authoritative coordinator.
-    //
-    // On contention we mark the run `cancelled`, not `failed`. The Dashboard
-    // "Needs attention" card only surfaces failed/timed_out/interrupted runs
-    // (see src/renderer/components/dashboard/Dashboard.tsx), so the user is
-    // not alarmed by a transient backoff. The task row is rolled back to
-    // `todo` via the `finishRun` never-started branch, so heartbeat picks
-    // it up on the next cycle with no manual intervention.
-    if (
-      params.workspaceMode === "exclusive" &&
-      params.workspace &&
-      !db.workspacesMod.claimWorkspaceLock(params.workspace.id, params.runId)
-    ) {
-      db.runs.finishRun({
-        runId: params.runId,
-        status: "cancelled",
-        summary: null,
-        errorMessage: `Workspace ${params.workspace.id} is in use by another run; will retry on the next heartbeat.`,
-        exitCode: null,
-        signal: null,
-        model: null,
-        unattributedCost: true,
+      // D-02: Claim the workspace lock synchronously before enqueuing the run.
+      // Previously the worker claimed the lock only after it emitted `running`,
+      // so two runs could race between enqueue and startup and both read the
+      // same workspace mid-write. Main is the authoritative coordinator.
+      //
+      // On contention we mark the run `cancelled`, not `failed`. The Dashboard
+      // "Needs attention" card only surfaces failed/timed_out/interrupted runs
+      // (see src/renderer/components/dashboard/Dashboard.tsx), so the user is
+      // not alarmed by a transient backoff. The task row is rolled back to
+      // `todo` via the `finishRun` never-started branch, so heartbeat picks
+      // it up on the next cycle with no manual intervention.
+      if (params.workspaceMode === "exclusive" && params.workspace) {
+        if (!db.workspacesMod.claimWorkspaceLock(params.workspace.id, params.runId)) {
+          db.runs.finishRun({
+            runId: params.runId,
+            status: "cancelled",
+            summary: null,
+            errorMessage: `Workspace ${params.workspace.id} is in use by another run; will retry on the next heartbeat.`,
+            exitCode: null,
+            signal: null,
+            model: null,
+            unattributedCost: true,
+          });
+          emitEvent({ type: "run-updated", runId: params.runId, action: "completed" });
+          return;
+        }
+        workspaceLockClaimed = true;
+      }
+
+      const payload = buildRunPayload(params, {
+        db,
+        logger,
+        getApiPort,
+        createRunToken,
+        listRuntimeSkillEntries,
+        getSessionHandoff,
+        evaluatePreRunSessionRotation,
       });
-      return;
+
+      enqueueWorkerRun(payload);
+    } catch (error) {
+      failRunBeforeWorkerEnqueue(params, error, workspaceLockClaimed);
     }
-
-    const payload = buildRunPayload(params, {
-      db,
-      logger,
-      getApiPort,
-      createRunToken,
-      listRuntimeSkillEntries,
-      getSessionHandoff,
-      evaluatePreRunSessionRotation,
-    });
-
-    enqueueWorkerRun(payload);
   }
 
   return { resolveWorkspace, getRunEligibilityFailure, dispatchRunToWorker };
diff --git a/src/main/orchestration/task-runner.ts b/src/main/orchestration/task-runner.ts
index 9750f374..3863cdb2 100644
--- a/src/main/orchestration/task-runner.ts
+++ b/src/main/orchestration/task-runner.ts
@@ -127,15 +127,18 @@ export function createTaskRunner(
       trigger,
       resolvedModel: assignment.modelId,
     });
-    db.activityMod.addActivity({
-      companyId: task.companyId,
-      actor,
-      action: "run.queued",
-      entityType: "run",
-      entityId: run.id,
-      detail: task.title,
-    });
-    emitEvent({ type: "run-updated", runId: run.id, action: "created" });
+    const postDispatchRun = db.runs.getRun(run.id);
+    if (postDispatchRun.status === "queued" || postDispatchRun.status === "running") {
+      db.activityMod.addActivity({
+        companyId: task.companyId,
+        actor,
+        action: "run.queued",
+        entityType: "run",
+        entityId: run.id,
+        detail: task.title,
+      });
+      emitEvent({ type: "run-updated", runId: run.id, action: "created" });
+    }
     return ok(run.id);
   }
 
diff --git a/src/main/orchestration/turn-context.ts b/src/main/orchestration/turn-context.ts
index d787c2ae..d7b27f76 100644
--- a/src/main/orchestration/turn-context.ts
+++ b/src/main/orchestration/turn-context.ts
@@ -54,7 +54,7 @@ export interface RunDispatchParams {
 
 export interface TurnContextDeps {
   db: AppDatabase;
-  logger: { info: (...args: unknown[]) => void; warn: (...args: unknown[]) => void };
+  logger: { info: (...args: unknown[]) => void; warn: (...args: unknown[]) => void; error?: (...args: unknown[]) => void };
   getApiPort: () => number;
   createRunToken: (agentId: string, companyId: string, runId: string) => string;
   listRuntimeSkillEntries: (companyId: string, agentId: string, connectorId: string) => ProjectedSkill[];
@@ -123,13 +123,13 @@ function resolveSessionHandoff(
   try {
     return deps.getSessionHandoff(agentId);
   } catch (err) {
-    logAppError(deps.logger, err, {
-      kind: "recoverable",
+    const appError = logAppError(deps.logger, err, {
+      kind: "upstream",
       code: "run.session_handoff.load_failed",
-      message: `Failed to load session handoff for agent ${agentId}; continuing without handoff`,
+      message: `Failed to load session handoff for agent ${agentId}.`,
       context: { agentId },
-    }, "warn");
-    return null;
+    });
+    throw appError;
   }
 }
 
@@ -143,13 +143,13 @@ function resolveSkills(
   try {
     return deps.listRuntimeSkillEntries(companyId, agentId, connectorId);
   } catch (err) {
-    logAppError(deps.logger, err, {
-      kind: "recoverable",
+    const appError = logAppError(deps.logger, err, {
+      kind: "upstream",
       code: "run.skills.fetch_failed",
-      message: `Failed to fetch managed skills for agent ${agentName}; proceeding with empty skill set`,
+      message: `Failed to fetch managed skills for agent ${agentName}.`,
       context: { agentId, agentName, connectorId, companyId },
-    }, "warn");
-    return [];
+    });
+    throw appError;
   }
 }
 
diff --git a/src/main/service-graph/create-orchestration-service.ts b/src/main/service-graph/create-orchestration-service.ts
index 728677f7..7438a980 100644
--- a/src/main/service-graph/create-orchestration-service.ts
+++ b/src/main/service-graph/create-orchestration-service.ts
@@ -73,41 +73,23 @@ export function buildOrchestrationService({
       workerService.getWorker()?.postMessage({ type: "enqueue-run", payload });
     },
     isQuitting: () => isQuittingRef.current,
-    listRuntimeSkillEntries: (companyId, agentId, connectorId) => {
-      try {
-        return skillService.listRuntimeSkillEntries(companyId, agentId, connectorId);
-      } catch (error) {
-        logger.warn(`[service-graph] listRuntimeSkillEntries failed for agent ${agentId}:`, error);
-        return [];
-      }
-    },
+    listRuntimeSkillEntries: (companyId, agentId, connectorId) =>
+      skillService.listRuntimeSkillEntries(companyId, agentId, connectorId),
     budgetService,
     checkpointEngine,
-    getSessionHandoff: (agentId) => {
-      try {
-        return sessionService.getHandoffForAgent(agentId);
-      } catch (error) {
-        logger.warn(`[service-graph] getSessionHandoff failed for agent ${agentId}:`, error);
-        return null;
-      }
-    },
-    evaluatePreRunSessionRotation: (agentId, connectorId) => {
-      try {
-        const agent = db.entityCrud.getAgent(agentId);
-        if (!agent.sessionId) return { rotated: false, handoff: null, sessionId: null };
-        const session = db.tasks.getSessionById(agent.sessionId);
-        if (!session) return { rotated: false, handoff: null, sessionId: agent.sessionId };
-        const result = sessionService.evaluateRotation(session);
-        if (result.shouldRotate) {
-          const newSessionId = sessionService.rotateSession(session);
-          const handoff = sessionService.getHandoffForAgent(agentId);
-          return { rotated: true, handoff, sessionId: newSessionId };
-        }
-        return { rotated: false, handoff: null, sessionId: agent.sessionId };
-      } catch (error) {
-        logger.warn(`[service-graph] evaluatePreRunSessionRotation failed for agent ${agentId}:`, error);
-        return { rotated: false, handoff: null, sessionId: null };
+    getSessionHandoff: (agentId) => sessionService.getHandoffForAgent(agentId),
+    evaluatePreRunSessionRotation: (agentId, _connectorId) => {
+      const agent = db.entityCrud.getAgent(agentId);
+      if (!agent.sessionId) return { rotated: false, handoff: null, sessionId: null };
+      const session = db.tasks.getSessionById(agent.sessionId);
+      if (!session) return { rotated: false, handoff: null, sessionId: agent.sessionId };
+      const result = sessionService.evaluateRotation(session);
+      if (result.shouldRotate) {
+        const newSessionId = sessionService.rotateSession(session);
+        const handoff = sessionService.getHandoffForAgent(agentId);
+        return { rotated: true, handoff, sessionId: newSessionId };
       }
+      return { rotated: false, handoff: null, sessionId: agent.sessionId };
     },
   });
 }
diff --git a/tests/unit/run-context-input-failures.test.ts b/tests/unit/run-context-input-failures.test.ts
new file mode 100644
index 00000000..4692d26d
--- /dev/null
+++ b/tests/unit/run-context-input-failures.test.ts
@@ -0,0 +1,184 @@
+import { join } from "node:path";
+import { tmpdir } from "node:os";
+import { mkdtemp, rm } from "node:fs/promises";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+
+vi.mock("electron", () => ({
+  safeStorage: {
+    isEncryptionAvailable: () => false,
+    getSelectedStorageBackend: () => "basic_text",
+    encryptString: (value: string) => Buffer.from(value, "utf8"),
+    decryptString: (value: Buffer) => value.toString("utf8"),
+  },
+}));
+
+import { AppDatabase } from "../../src/main/database";
+import { createBudgetEnforcementService } from "../../src/main/budget-enforcement-service";
+import { createRunDispatch } from "../../src/main/orchestration/run-dispatch";
+import { createTaskRunner } from "../../src/main/orchestration/task-runner";
+import type { OrchestrationDependencies } from "../../src/main/orchestration/types";
+
+function createLogger() {
+  return {
+    debug: vi.fn(),
+    info: vi.fn(),
+    warn: vi.fn(),
+    error: vi.fn(),
+  };
+}
+
+function createCompanyRunFixture(db: AppDatabase, profileDir: string) {
+  db.connectorsCrud.updateConnectorHealth({
+    id: "openai-codex",
+    status: "ready",
+    authState: "authenticated",
+    version: "test",
+    lastError: null,
+  });
+  const companyId = db.company.saveCompany({
+    name: "Context Integrity Co",
+    description: "Validates run context failures",
+    status: "active",
+  });
+  const workspaceId = db.workspacesMod.saveWorkspace({
+    companyId,
+    name: "Primary",
+    localPath: profileDir,
+    repoUrl: "",
+    repoRef: "",
+    isPrimary: true,
+  });
+  const agentId = db.agents.saveAgent({
+    companyId,
+    name: "Runtime Engineer",
+    role: "Engineer",
+    title: "Runtime Engineer",
+    status: "idle",
+    reportsTo: null,
+    connectorId: "openai-codex",
+    workspaceId,
+    model: "gpt-5.4",
+    capabilities: "Ships runtime fixes",
+    budgetMonthlyUsd: 250,
+  });
+  const taskId = db.tasks.saveTask({
+    companyId,
+    title: "Assemble safe run context",
+    description: "The worker must start only with a complete context.",
+    assigneeAgentId: agentId,
+    workspaceId,
+    priority: "high",
+    status: "todo",
+    requiresFilesystem: true,
+  });
+  return { companyId, workspaceId, agentId, taskId };
+}
+
+function createHarness(
+  db: AppDatabase,
+  overrides: Partial<Pick<OrchestrationDependencies, "listRuntimeSkillEntries" | "getSessionHandoff">> = {},
+) {
+  const logger = createLogger();
+  const enqueueWorkerRun = vi.fn();
+  const emitEvent = vi.fn();
+  const budgetService = createBudgetEnforcementService({
+    db,
+    logger,
+    notify: vi.fn(),
+    publishDomainChanged: vi.fn(),
+  });
+  const deps: OrchestrationDependencies = {
+    db,
+    logger,
+    publishDomainChanged: vi.fn(),
+    emitEvent,
+    notify: vi.fn(),
+    createRunToken: () => "test-token",
+    getApiPort: () => 3210,
+    dispatchAutomation: vi.fn(),
+    hasWorkerReady: () => true,
+    enqueueWorkerRun,
+    isQuitting: () => false,
+    listRuntimeSkillEntries: () => [],
+    budgetService,
+    checkpointEngine: { shouldPauseHeartbeat: () => false },
+    ...overrides,
+  };
+  const runDispatch = createRunDispatch(deps);
+  const taskRunner = createTaskRunner(
+    deps,
+    runDispatch.resolveWorkspace,
+    runDispatch.getRunEligibilityFailure,
+    runDispatch.dispatchRunToWorker,
+    (filter) => db.runs.hasActiveRun(filter),
+  );
+  return { enqueueWorkerRun, emitEvent, logger, taskRunner };
+}
+
+describe("run context input failures", () => {
+  let tempDir: string;
+  let db: AppDatabase;
+
+  beforeEach(async () => {
+    tempDir = await mkdtemp(join(tmpdir(), "agentcompany-context-input-"));
+    db = new AppDatabase(tempDir);
+    db.init();
+  });
+
+  afterEach(async () => {
+    db.close();
+    await rm(tempDir, { recursive: true, force: true });
+  });
+
+  it("fails the run before worker enqueue when managed skills cannot load", () => {
+    const { taskId } = createCompanyRunFixture(db, tempDir);
+    const { enqueueWorkerRun, emitEvent, taskRunner } = createHarness(db, {
+      listRuntimeSkillEntries: () => {
+        throw new Error("skill database unavailable");
+      },
+    });
+
+    const result = taskRunner.queueTaskRun(taskId, "manual", "unit-test");
+
+    expect(result.ok).toBe(true);
+    if (!result.ok) {
+      throw new Error("Expected the task runner to persist a failed run.");
+    }
+    expect(enqueueWorkerRun).not.toHaveBeenCalled();
+    const run = db.runs.getRun(result.data);
+    const task = db.entityCrud.getTask(taskId);
+    const workspace = db.workspacesMod.getWorkspace(task.workspaceId);
+    expect(run.status).toBe("failed");
+    expect(run.errorMessage).toContain("run.skills.fetch_failed");
+    expect(task.status).toBe("todo");
+    expect(task.activeRunId).toBeNull();
+    expect(workspace?.state).toBe("ready");
+    expect(emitEvent).toHaveBeenCalledWith({ type: "run-updated", runId: run.id, action: "completed" });
+    expect(emitEvent).not.toHaveBeenCalledWith({ type: "run-updated", runId: run.id, action: "created" });
+  });
+
+  it("fails the run before worker enqueue when session handoff cannot load", () => {
+    const { taskId } = createCompanyRunFixture(db, tempDir);
+    const { enqueueWorkerRun, emitEvent, taskRunner } = createHarness(db, {
+      getSessionHandoff: () => {
+        throw new Error("session handoff store unavailable");
+      },
+    });
+
+    const result = taskRunner.queueTaskRun(taskId, "manual", "unit-test");
+
+    expect(result.ok).toBe(true);
+    if (!result.ok) {
+      throw new Error("Expected the task runner to persist a failed run.");
+    }
+    expect(enqueueWorkerRun).not.toHaveBeenCalled();
+    const run = db.runs.getRun(result.data);
+    const task = db.entityCrud.getTask(taskId);
+    expect(run.status).toBe("failed");
+    expect(run.errorMessage).toContain("run.session_handoff.load_failed");
+    expect(task.status).toBe("todo");
+    expect(task.activeRunId).toBeNull();
+    expect(emitEvent).toHaveBeenCalledWith({ type: "run-updated", runId: run.id, action: "completed" });
+    expect(emitEvent).not.toHaveBeenCalledWith({ type: "run-updated", runId: run.id, action: "created" });
+  });
+});