diff --git a/src/main/automations/service.test.ts b/src/main/automations/service.test.ts
index 9ab1ed45d57..786ff017bb2 100644
--- a/src/main/automations/service.test.ts
+++ b/src/main/automations/service.test.ts
@@ -348,6 +348,70 @@ describe('AutomationService', () => {
     )
   })
 
+  it('dispatches due scheduled automations headlessly', async () => {
+    const timezone = Intl.DateTimeFormat().resolvedOptions().timeZone
+    const beforeRunAt = new Date(2026, 4, 13, 8, 59).getTime()
+    const scheduledRunAt = new Date(2026, 4, 13, 9, 0).getTime()
+    const afterRunAt = new Date(2026, 4, 13, 9, 1).getTime()
+    const nextRunAt = new Date(2026, 4, 14, 9, 0).getTime()
+
+    vi.setSystemTime(beforeRunAt)
+    const store = await createStore()
+    const runtimeHostId = toRuntimeExecutionHostId('gpu-server')
+    store.addRepo(makeRepo({ executionHostId: runtimeHostId }))
+    const setup = store.getProjectHostSetups()[0]!
+    const automation = store.createAutomation({
+      name: 'Morning check',
+      prompt: 'Check the repo',
+      agentId: 'claude',
+      projectId: 'r1',
+      runContext: {
+        kind: 'workspace-run',
+        projectId: setup.projectId,
+        hostId: runtimeHostId,
+        projectHostSetupId: setup.id,
+        repoId: setup.repoId,
+        path: setup.path
+      },
+      workspaceMode: 'new_per_run',
+      timezone,
+      rrule: 'FREQ=DAILY;BYHOUR=9;BYMINUTE=0',
+      dtstart: new Date(2026, 4, 12, 0, 0).getTime()
+    })
+
+    const headlessDispatcher = vi.fn().mockResolvedValue({
+      workspaceId: 'wt1',
+      workspaceDisplayName: 'Morning check',
+      terminalSessionId: 'tab-1',
+      terminalPaneKey: 'pane-1',
+      terminalPtyId: 'pty-1'
+    })
+    const service = new AutomationService(store, {
+      tickMs: 60_000,
+      allowRemoteHostScheduling: true,
+      headlessDispatcher
+    })
+
+    try {
+      vi.setSystemTime(afterRunAt)
+      service.start()
+      await vi.waitFor(() => expect(headlessDispatcher).toHaveBeenCalledTimes(1))
+      const run = store.listAutomationRuns(automation.id)[0]
+      expect(run?.status).toBe('dispatched')
+      expect(run?.scheduledFor).toBe(scheduledRunAt)
+      expect(headlessDispatcher).toHaveBeenCalledWith(
+        expect.objectContaining({ automation: expect.objectContaining({ id: automation.id }) })
+      )
+      await vi.waitFor(() =>
+        expect(store.listAutomations().find((entry) => entry.id === automation.id)?.nextRunAt).toBe(
+          nextRunAt
+        )
+      )
+    } finally {
+      service.stop()
+    }
+  })
+
   it('attaches provider usage when a completed run can be attributed', async () => {
     vi.setSystemTime(new Date('2026-05-13T10:00:00'))
     const store = await createStore()
diff --git a/src/main/automations/service.ts b/src/main/automations/service.ts
index 7a192153d1f..dc22550e7ec 100644
--- a/src/main/automations/service.ts
+++ b/src/main/automations/service.ts
@@ -69,7 +69,9 @@ export class AutomationService {
     this.timer = setInterval(() => {
       void this.evaluateDueRuns()
     }, this.tickMs)
-    if (this.rendererReady) {
+    // Why: headless serve never gets a renderer-ready IPC, but due runs still
+    // need the same startup catch-up pass desktop gets after renderer attach.
+    if (this.rendererReady || this.headlessDispatcher) {
       void this.evaluateDueRuns()
     }
   }
diff --git a/src/main/index.ts b/src/main/index.ts
index 9537dc98b38..ff4b249f8dc 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -2095,6 +2095,8 @@ app.whenReady().then(async () => {
         )
       }
     }
+    // Why: headless serve never opens a renderer, so arm scheduled automation dispatch here.
+    automations.start()
     await printServeReady(serveOptions)
     return
   }
diff --git a/src/main/startup/desktop-startup-ordering.test.ts b/src/main/startup/desktop-startup-ordering.test.ts
index cd1faf35c60..276242040dc 100644
--- a/src/main/startup/desktop-startup-ordering.test.ts
+++ b/src/main/startup/desktop-startup-ordering.test.ts
@@ -32,4 +32,28 @@ describe('desktop startup ordering', () => {
     expect(attachIndex).toBeGreaterThanOrEqual(0)
     expect(startIndex).toBeGreaterThan(attachIndex)
   })
+
+  it('starts the automation scheduler before headless serve reports ready', () => {
+    const source = readFileSync(join(process.cwd(), 'src/main/index.ts'), 'utf8')
+    const serveStart = source.indexOf('if (serveOptions) {')
+    const serveReady = source.indexOf('await printServeReady(serveOptions)', serveStart)
+    const serveReturn = source.indexOf('return', serveReady)
+    const runtimeRpcStart = source.indexOf('await runtimeRpc.start()', serveStart)
+    const automationStart = source.indexOf('automations.start()', serveStart)
+    const desktopSetWebContents = source.indexOf('automations.setWebContents(window.webContents)')
+    const desktopAutomationStart = source.indexOf(
+      'automations.start()',
+      desktopSetWebContents + 1
+    )
+
+    expect(serveStart).toBeGreaterThanOrEqual(0)
+    expect(serveReady).toBeGreaterThan(serveStart)
+    expect(serveReturn).toBeGreaterThan(serveReady)
+    expect(runtimeRpcStart).toBeGreaterThan(serveStart)
+    expect(automationStart).toBeGreaterThan(runtimeRpcStart)
+    expect(automationStart).toBeLessThan(serveReady)
+    expect(automationStart).toBeLessThan(serveReturn)
+    expect(desktopSetWebContents).toBeGreaterThanOrEqual(0)
+    expect(desktopAutomationStart).toBeGreaterThan(desktopSetWebContents)
+  })
 })