diff --git a/src/main/host/deferred-secret-protection-report.test.ts b/src/main/host/deferred-secret-protection-report.test.ts
index 97141a6f736..2e70d5268a0 100644
--- a/src/main/host/deferred-secret-protection-report.test.ts
+++ b/src/main/host/deferred-secret-protection-report.test.ts
@@ -73,7 +73,11 @@ describe('scheduleSecretProtectionGapReport', () => {
   })
 
   const schedule = (): void =>
-    scheduleSecretProtectionGapReport({ dataFile, log: (m) => void logged.push(m) })
+    scheduleSecretProtectionGapReport({
+      dataFile,
+      log: (m) => void logged.push(m),
+      deferUntilFirstWindow: true
+    })
 
   /** Runs an already-queued setImmediate; the 1ms is slack, not a delay under test. */
   const drain = (): void => void vi.advanceTimersByTime(1)
@@ -127,4 +131,27 @@ describe('scheduleSecretProtectionGapReport', () => {
     vi.runAllTimers()
     expect(probes).toBe(1)
   })
+
+  it('reports inline in headless serve, before the runtime is advertised as ready', () => {
+    // Why not deferred: serve opens no window, so the fallback would fire only after
+    // clients could already have paired, and a frozen main thread reads as a dead host.
+    scheduleSecretProtectionGapReport({
+      dataFile,
+      log: (m) => void logged.push(m),
+      deferUntilFirstWindow: false
+    })
+    expect(probes).toBe(1)
+    expect(logged).toEqual(['[secrets] The OS keyring is unavailable.'])
+  })
+
+  it('leaves no timer armed in headless serve', () => {
+    scheduleSecretProtectionGapReport({
+      dataFile,
+      log: (m) => void logged.push(m),
+      deferUntilFirstWindow: false
+    })
+    expect(vi.getTimerCount()).toBe(0)
+    vi.runAllTimers()
+    expect(probes).toBe(1)
+  })
 })
diff --git a/src/main/host/deferred-secret-protection-report.ts b/src/main/host/deferred-secret-protection-report.ts
index cf2c7da2493..01a7277ec61 100644
--- a/src/main/host/deferred-secret-protection-report.ts
+++ b/src/main/host/deferred-secret-protection-report.ts
@@ -19,11 +19,27 @@ import { reportSecretProtectionGap } from './secret-protection-report'
 // serve has no window to wait on.
 const REPORT_FALLBACK_MS = 15_000
 
-export function scheduleSecretProtectionGapReport(options: {
+export function scheduleSecretProtectionGapReport({
+  deferUntilFirstWindow,
+  ...options
+}: {
   dataFile: string
   force?: boolean
   log?: (message: string) => void
+  /**
+   * Why headless serve reports inline instead: it never opens a window, so the fallback
+   * timer is the only path — and by then the runtime has been advertised as ready and
+   * clients may have paired. Freezing the main thread under a live client stalls pings
+   * and PTY pumps, which reads as a dead host. Blocking before anything is advertised is
+   * the timing serve already had, and the safer of the two.
+   */
+  deferUntilFirstWindow: boolean
 }): void {
+  if (!deferUntilFirstWindow) {
+    reportSecretProtectionGap(options)
+    return
+  }
+
   let ran = false
   const run = (): void => {
     if (ran) {
diff --git a/src/main/index.ts b/src/main/index.ts
index dc8eeaccd91..39d27bada72 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -2352,7 +2352,8 @@ void app.whenReady().then(async () => {
   // and must not gate the first window (STA-5765).
   scheduleSecretProtectionGapReport({
     dataFile: activeOrcaProfile.dataFile,
-    force: process.env.ORCA_ALWAYS_REPORT_SECRET_PROTECTION === '1'
+    force: process.env.ORCA_ALWAYS_REPORT_SECRET_PROTECTION === '1',
+    deferUntilFirstWindow: !isServeMode
   })
   // Why here: the host key store is a sidecar of the same profile, and every SSH connect consults
   // it. Left unbound it reports nothing trusted, which is safe but silently discards our own