diff --git a/apps/desktop/electron/cloud-session-recovery.test.ts b/apps/desktop/electron/cloud-session-recovery.test.ts
new file mode 100644
index 0000000000..72d676f3c7
--- /dev/null
+++ b/apps/desktop/electron/cloud-session-recovery.test.ts
@@ -0,0 +1,107 @@
+import { describe, expect, it, vi } from 'vitest'
+
+import { createCloudSessionRecovery } from './cloud-session-recovery'
+
+const cloud = 'https://test-agent.agents.nousresearch.com'
+const rejection = (statusCode = 401) => Object.assign(new Error('rejected'), { statusCode })
+
+describe('Cloud cookie session recovery', () => {
+  it('recovers an expired cookie session before minting a new ticket', async () => {
+    const restore = vi.fn(async () => true)
+    const run = createCloudSessionRecovery({ hasNativeSession: () => false, restoreCookieSession: restore })
+    const mint = vi.fn().mockRejectedValueOnce(rejection()).mockResolvedValueOnce('fresh-ticket')
+    expect(await run(cloud, mint)).toBe('fresh-ticket')
+    expect(restore).toHaveBeenCalledExactlyOnceWith(cloud)
+    expect(mint).toHaveBeenCalledTimes(2)
+  })
+
+  it('does not recover non-Cloud, non-401 or native-session failures', async () => {
+    const restore = vi.fn(async () => true)
+
+    const run = createCloudSessionRecovery({
+      hasNativeSession: url => url.endsWith('native.agents.nousresearch.com'),
+      restoreCookieSession: restore
+    })
+
+    for (const [url, status] of [
+      ['https://example.com', 401],
+      [cloud, 403],
+      [cloud, 500],
+      ['https://native.agents.nousresearch.com', 401]
+    ] as const) {
+      const error = rejection(status)
+      await expect(
+        run(url, async () => {
+          throw error
+        })
+      ).rejects.toBe(error)
+    }
+
+    expect(restore).not.toHaveBeenCalled()
+  })
+
+  it('coalesces recovery without reusing single-use tickets', async () => {
+    let release!: (restored: boolean) => void
+
+    const restore = vi.fn(
+      () =>
+        new Promise<boolean>(resolve => {
+          release = resolve
+        })
+    )
+
+    const run = createCloudSessionRecovery({ hasNativeSession: () => false, restoreCookieSession: restore })
+    const firstMint = vi.fn().mockRejectedValueOnce(rejection()).mockResolvedValueOnce('ticket-1')
+    const secondMint = vi.fn().mockRejectedValueOnce(rejection()).mockResolvedValueOnce('ticket-2')
+    const first = run(cloud, firstMint)
+    const second = run(cloud, secondMint)
+    await vi.waitFor(() => expect(restore).toHaveBeenCalledTimes(1))
+    release(true)
+    expect(await Promise.all([first, second])).toEqual(['ticket-1', 'ticket-2'])
+  })
+
+  it('does not retry under a native identity selected during background recovery', async () => {
+    let native = false
+
+    const restore = vi.fn(async () => {
+      native = true
+
+      return true
+    })
+
+    const run = createCloudSessionRecovery({ hasNativeSession: () => native, restoreCookieSession: restore })
+    const error = rejection()
+
+    const mint = vi.fn(async () => {
+      throw error
+    })
+
+    await expect(run(cloud, mint)).rejects.toBe(error)
+    expect(mint).toHaveBeenCalledTimes(1)
+  })
+
+  it('backs off failed recovery and bounds a successful recovery to one retry', async () => {
+    let clock = 0
+    const restore = vi.fn().mockResolvedValueOnce(false).mockResolvedValue(true)
+
+    const run = createCloudSessionRecovery({
+      hasNativeSession: () => false,
+      restoreCookieSession: restore,
+      now: () => clock
+    })
+
+    const error = rejection()
+
+    const mint = vi.fn(async () => {
+      throw error
+    })
+
+    await expect(run(cloud, mint)).rejects.toBe(error)
+    await expect(run(cloud, mint)).rejects.toBe(error)
+    expect(restore).toHaveBeenCalledTimes(1)
+    clock = 60_001
+    await expect(run(cloud, mint)).rejects.toBe(error)
+    expect(restore).toHaveBeenCalledTimes(2)
+    expect(mint).toHaveBeenCalledTimes(4)
+  })
+})
diff --git a/apps/desktop/electron/cloud-session-recovery.ts b/apps/desktop/electron/cloud-session-recovery.ts
new file mode 100644
index 0000000000..afcd887578
--- /dev/null
+++ b/apps/desktop/electron/cloud-session-recovery.ts
@@ -0,0 +1,76 @@
+import { isNousCloudAgentUrl } from './backend-health'
+
+interface CloudRecoveryDeps {
+  hasNativeSession: (baseUrl: string) => boolean
+  restoreCookieSession: (baseUrl: string) => Promise<boolean>
+  onRecovered?: (baseUrl: string) => void
+  now?: () => number
+}
+
+/** Coalesce the cookie refresh, never the single-use ticket minted afterward. */
+export function createCloudSessionRecovery(deps: CloudRecoveryDeps) {
+  const inflight = new Map<string, Promise<boolean>>()
+  const failedAt = new Map<string, number>()
+  const now = deps.now ?? Date.now
+
+  return async <T>(baseUrl: string, mint: () => Promise<T>): Promise<T> => {
+    const hadNativeSession = deps.hasNativeSession(baseUrl)
+
+    try {
+      return await mint()
+    } catch (error) {
+      if (
+        !isNousCloudAgentUrl(baseUrl) ||
+        hadNativeSession ||
+        deps.hasNativeSession(baseUrl) ||
+        (error as { statusCode?: number })?.statusCode !== 401
+      ) {
+        throw error
+      }
+
+      let recovery = inflight.get(baseUrl)
+
+      if (!recovery) {
+        const failed = failedAt.get(baseUrl)
+
+        if (failed !== undefined && now() - failed < 60_000) {
+          throw error
+        }
+
+        recovery = Promise.resolve()
+          .then(() => deps.restoreCookieSession(baseUrl))
+          .catch(() => false)
+          .then(restored => {
+            if (!restored) {
+              failedAt.set(baseUrl, now())
+            }
+
+            return restored
+          })
+          .finally(() => inflight.delete(baseUrl))
+        inflight.set(baseUrl, recovery)
+      }
+
+      if (!(await recovery)) {
+        throw error
+      }
+
+      // Native login may have changed while the background cookie flow ran.
+      // Never turn that transition into a cross-identity fallback.
+      if (deps.hasNativeSession(baseUrl)) {
+        throw error
+      }
+
+      try {
+        const ticket = await mint()
+        failedAt.delete(baseUrl)
+        deps.onRecovered?.(baseUrl)
+
+        return ticket
+      } catch (retryError) {
+        failedAt.set(baseUrl, now())
+        throw retryError
+      }
+    }
+  }
+}
diff --git a/apps/desktop/electron/connection-caches.test.ts b/apps/desktop/electron/connection-caches.test.ts
index 4c665463f7..5c1e7cca40 100644
--- a/apps/desktop/electron/connection-caches.test.ts
+++ b/apps/desktop/electron/connection-caches.test.ts
@@ -5,6 +5,7 @@ import { beforeEach, test } from 'vitest'
 import {
   connectionInstallIds,
   evictConnectionCaches,
+  rosterSourceErrors,
   sshInventoryAttemptedAt,
   sshRosterCache
 } from './connection-caches'
@@ -14,12 +15,14 @@ beforeEach(() => {
   sshRosterCache.clear()
   sshInventoryAttemptedAt.clear()
   connectionInstallIds.clear()
+  rosterSourceErrors.clear()
 })
 
 function seed(id: string) {
   sshRosterCache.set(id, ['default', 'dixie'])
   sshInventoryAttemptedAt.set(id, Date.now())
   connectionInstallIds.set(id, { id: 'aaa', ts: Date.now() })
+  rosterSourceErrors.set(id, 'previous failure')
 }
 
 test('evicting a connection id forgets every cache keyed by it', () => {
@@ -33,10 +36,12 @@ test('evicting a connection id forgets every cache keyed by it', () => {
   assert.equal(sshRosterCache.has('mac-mini'), false)
   assert.equal(sshInventoryAttemptedAt.has('mac-mini'), false)
   assert.equal(connectionInstallIds.has('mac-mini'), false)
+  assert.equal(rosterSourceErrors.has('mac-mini'), false)
 
   // Its neighbours are untouched.
   assert.deepEqual(sshRosterCache.get('spark'), ['default', 'dixie'])
   assert.equal(connectionInstallIds.get('spark')?.id, 'aaa')
+  assert.equal(rosterSourceErrors.get('spark'), 'previous failure')
 })
 
 test('an evicted id enumerates from the live target again instead of serving the old one', () => {
@@ -66,4 +71,5 @@ test('evicting an unknown or empty id is a no-op', () => {
   assert.equal(sshRosterCache.size, 1)
   assert.equal(sshInventoryAttemptedAt.size, 1)
   assert.equal(connectionInstallIds.size, 1)
+  assert.equal(rosterSourceErrors.size, 1)
 })
diff --git a/apps/desktop/electron/connection-caches.ts b/apps/desktop/electron/connection-caches.ts
index ac02b2aa49..fc15660fe2 100644
--- a/apps/desktop/electron/connection-caches.ts
+++ b/apps/desktop/electron/connection-caches.ts
@@ -24,7 +24,15 @@ export const sshInventoryAttemptedAt = new Map<string, number>()
  */
 export const connectionInstallIds = new Map<string, { id?: string; ts: number }>()
 
-const CONNECTION_SCOPED_CACHES: Map<string, unknown>[] = [sshRosterCache, sshInventoryAttemptedAt, connectionInstallIds]
+/** Last logged roster failure per connection, so repeat polls do not spam the log. */
+export const rosterSourceErrors = new Map<string, string>()
+
+const CONNECTION_SCOPED_CACHES: Map<string, unknown>[] = [
+  sshRosterCache,
+  sshInventoryAttemptedAt,
+  connectionInstallIds,
+  rosterSourceErrors
+]
 
 /**
  * Forget everything cached about a connection id. Call whenever that id stops naming the machine
diff --git a/apps/desktop/electron/main.ts b/apps/desktop/electron/main.ts
index 1d59212503..0f5f9d277d 100644
--- a/apps/desktop/electron/main.ts
+++ b/apps/desktop/electron/main.ts
@@ -114,12 +114,14 @@ import { provisionCliLinks } from './cli-provision'
 import { closeStopFailureMessage, finishWindowsCloseStop, type RuntimeLock } from './close-stop-kill'
 import { shouldAttemptCloudBootCascade } from './cloud-boot-cascade'
 import { discoverWithTeamFallback } from './cloud-discovery'
+import { createCloudSessionRecovery } from './cloud-session-recovery'
 import { installCommandScreenshot } from './command-screenshot'
 import { writeComposerPaste } from './composer-paste'
 import { applyConnectionChange, teardownSshState } from './connection-apply'
 import {
   connectionInstallIds,
   evictConnectionCaches,
+  rosterSourceErrors,
   sshInventoryAttemptedAt,
   sshRosterCache
 } from './connection-caches'
@@ -453,6 +455,7 @@ import { planLaunchSwitches, readDesktopLaunchConfig } from './renderer-heap-fla
 import { loadRendererLoadErrorPage } from './renderer-load-error-page'
 import { attachRendererConsoleCapture, formatRendererBoundaryReport } from './renderer-log'
 import { fetchRosterSourceData } from './roster-source-fetch'
+import { rosterSourceStatus } from './roster-source-status'
 import {
   classifyStoredSecret,
   readSecretStoragePolicy,
@@ -7441,7 +7444,7 @@ async function clearOauthSession(baseUrl) {
 //     ``/auth/login`` → portal ``/oauth/authorize`` (auto-approves org members)
 //     → ``/auth/callback``, which sets the gateway cookie with NO interactive
 //     prompt. This is the per-agent cloud cascade (decisions.md Q5).
-function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
+function openOauthLoginWindow(baseUrl, { silent = false, background = false } = {}) {
   return new Promise((resolve, reject) => {
     if (!app.isReady()) {
       reject(new Error('Desktop is not ready to start an OAuth login.'))
@@ -7461,6 +7464,7 @@ function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
     let win = null
     let pollTimer = null
     let revealTimer = null
+    let deadlineTimer = null
 
     const finish = err => {
       if (settled) {
@@ -7477,6 +7481,10 @@ function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
         clearTimeout(revealTimer)
       }
 
+      if (deadlineTimer) {
+        clearTimeout(deadlineTimer)
+      }
+
       try {
         if (win && !win.isDestroyed()) {
           win.destroy()
@@ -7513,7 +7521,7 @@ function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
         // only reveal it as a fallback if the cascade DOESN'T complete quickly
         // (e.g. the portal session lapsed and the gate fell through to the
         // interactive chooser) — see the reveal timer below.
-        show: !silent,
+        show: !silent && !background,
         webPreferences: {
           contextIsolation: true,
           nodeIntegration: false,
@@ -7545,7 +7553,7 @@ function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
     // loop-guard tripped, etc.) and the window is now showing an interactive
     // page. Reveal it so the user can complete sign-in manually rather than
     // staring at nothing. Cleared on finish().
-    if (silent && win) {
+    if (silent && win && !background) {
       revealTimer = setTimeout(() => {
         try {
           if (!settled && win && !win.isDestroyed() && !win.isVisible()) {
@@ -7557,6 +7565,10 @@ function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
       }, 2500)
     }
 
+    if (background) {
+      deadlineTimer = setTimeout(() => finish(new Error('Cloud session recovery requires sign-in.')), 12_000)
+    }
+
     win.on('closed', () => {
       if (!settled) {
         finish(new Error('Login window closed before authentication completed.'))
@@ -7576,6 +7588,14 @@ function openOauthLoginWindow(baseUrl, { silent = false } = {}) {
       `OAuth login: attaching ${Object.keys(loginHeaders).length} extra gateway header(s) to ${new URL(normalizedBase).host}`
     )
     win.loadURL(loginUrl, oauthLoginLoadUrlOptions(loginHeaders)).catch(error => {
+      // Callback navigation can abort the original load after setting cookies.
+      // Keep the bounded hidden recovery alive long enough to observe them.
+      if (background && (Number(error?.code) === -3 || /\bERR_ABORTED\b/.test(String(error?.message)))) {
+        void checkCookie()
+
+        return
+      }
+
       finish(error instanceof Error ? error : new Error(String(error)))
     })
   })
@@ -7876,20 +7896,40 @@ async function readGatewayFileDataUrl(connection: GatewayFileConnection, request
   return dataUrl
 }
 
-// Mint a single-use WS ticket for a gated gateway. Native bearer first (one
-// forced rotation on a confirmed 401, #95701), OAuth cookie partition second.
-// Transient transport blips (brief host unreachable, 5xx, timeouts) are retried
-// a few times before failing — those 1-3s flaps were promoting into the
-// full-screen "couldn't start" lockout on reconnect. Ticket POSTs are
-// replay-safe; arbitrary REST mutations never use this retry loop.
-async function mintGatewayWsTicket(baseUrl: string, headers: Record<string, string> = {}): Promise<string> {
-  return withTransientRetries(
-    (): Promise<string> =>
-      mintOauthGatewayWsTicket(baseUrl, { ensureNativeAccessToken, fetchJson, fetchJsonViaOauthSession }, headers),
-    {
-      isRetryable: (error: Error): boolean =>
-        !(error instanceof NativeAuthChangedError) && !isGatewayAuthRejection(error)
+// Recover a Cloud cookie only after a confirmed cookie-auth ticket 401.
+// Each caller still mints its own single-use ticket after the shared recovery.
+const recoverCloudCookieSession = createCloudSessionRecovery({
+  hasNativeSession,
+  onRecovered: baseUrl => rememberLog(`[cloud] saved gateway session recovered for ${hostLabelFromBaseUrl(baseUrl)}`),
+  restoreCookieSession: async baseUrl => {
+    // The saved portal identity is the authority for cookie agent sessions.
+    // Roster polling must never reveal an interactive sign-in window.
+    if (!(await hasLivePortalSession())) {
+      return false
     }
+
+    if (!(await hasPortalAccessToken()) && !(await renewPortalAccessSilently())) {
+      return false
+    }
+
+    await openOauthLoginWindow(baseUrl, { silent: true, background: true })
+
+    return true
+  }
+})
+
+// Native bearer first (including one forced 401 rotation), OAuth cookie second.
+// Transient ticket POST failures keep their bounded retry before Cloud recovery.
+async function mintGatewayWsTicket(baseUrl: string, headers: Record<string, string> = {}): Promise<string> {
+  return recoverCloudCookieSession(baseUrl, () =>
+    withTransientRetries(
+      (): Promise<string> =>
+        mintOauthGatewayWsTicket(baseUrl, { ensureNativeAccessToken, fetchJson, fetchJsonViaOauthSession }, headers),
+      {
+        isRetryable: (error: Error): boolean =>
+          !(error instanceof NativeAuthChangedError) && !isGatewayAuthRejection(error)
+      }
+    )
   )
 }
 
@@ -15706,7 +15746,7 @@ ipcMain.handle('hermes:connections:test', async (_event, id) => {
 // would spawn tunnels the user never asked for); once dialed, their pooled
 // descriptor serves the enumeration like any remote. Last-known SSH profile
 // lists are reused so switching the window back to local does not empty Bot Mode.
-// These three live in ./connection-caches, which states (and tests) the invariant they share:
+// Connection caches live in ./connection-caches, which states (and tests) the invariant they share:
 // each is keyed by connection id and is only valid while that id names the same machine, so
 // removing a connection or re-pointing it must evict them (`evictConnectionCaches`).
 const SSH_INVENTORY_RETRY_MS = 60_000
@@ -15837,9 +15877,12 @@ async function enumerateRegistryAgentSources(registry = readDesktopConnectionsRe
 
   return Promise.all(
     registry.connections.map(async connection => {
+      let sourceFailureDetail = ''
+
       let raw: {
         connection: typeof connection
         error?: string
+        needsSignIn?: boolean
         installId?: string
         profiles: null | string[]
         profileMetadata?: Record<string, RosterProfileMetadata>
@@ -15953,7 +15996,26 @@ async function enumerateRegistryAgentSources(registry = readDesktopConnectionsRe
           }
         }
       } catch (error: any) {
-        raw = { connection, profiles: null, error: String(error?.message || error) }
+        sourceFailureDetail = [error?.statusCode, error?.cause?.message].filter(Boolean).join(' | ')
+        raw = {
+          connection,
+          profiles: null,
+          error: redactSecrets(String(error?.message || error)),
+          needsSignIn: isReauthRequiredError(error)
+        }
+      }
+
+      if (raw.error && raw.error !== 'connect-on-demand') {
+        const diagnostic = redactSecrets([raw.error, sourceFailureDetail].filter(Boolean).join(' | '))
+          .replace(/[\r\n]+/g, ' ')
+          .slice(0, 800)
+
+        if (rosterSourceErrors.get(connection.id) !== diagnostic) {
+          rememberLog(`[fleet-roster] ${connection.id}: ${diagnostic}`)
+          rosterSourceErrors.set(connection.id, diagnostic)
+        }
+      } else if (raw.profiles && rosterSourceErrors.delete(connection.id)) {
+        rememberLog(`[fleet-roster] ${connection.id}: connection recovered`)
       }
 
       if (raw.profiles && raw.profiles.length > 0) {
@@ -15965,6 +16027,7 @@ async function enumerateRegistryAgentSources(registry = readDesktopConnectionsRe
       return {
         connection,
         ...remembered,
+        ...(raw.needsSignIn ? { needsSignIn: true } : {}),
         ...(raw.installId ? { installId: raw.installId } : {}),
         ...(raw.profileMetadata ? { profileMetadata: raw.profileMetadata } : {})
       }
@@ -15984,13 +16047,12 @@ ipcMain.handle('hermes:agents:roster', async () => {
     // instead of appending duplicates (remote-only desktops doubled every
     // bot otherwise; see #88344).
     primaryConnectionId: registry.primary,
-    sources: enumerations.map(({ connection, error, installId, profiles }) => ({
+    sources: enumerations.map(({ connection, error, installId, profiles, needsSignIn }) => ({
       connectionId: connection.id,
       label: connection.label,
       kind: connection.kind,
-      reachable: profiles !== null,
-      ...(installId ? { installId } : {}),
-      ...(error ? { error } : {})
+      ...rosterSourceStatus({ profiles, error, needsSignIn }),
+      ...(installId ? { installId } : {})
     }))
   }
 })
diff --git a/apps/desktop/electron/roster-source-status.test.ts b/apps/desktop/electron/roster-source-status.test.ts
new file mode 100644
index 0000000000..5255f8b3df
--- /dev/null
+++ b/apps/desktop/electron/roster-source-status.test.ts
@@ -0,0 +1,13 @@
+import { expect, it } from 'vitest'
+
+import { rosterSourceStatus } from './roster-source-status'
+
+it('does not report stale cached profiles as a reachable or signed-in gateway', () => {
+  expect(rosterSourceStatus({ profiles: ['default'], error: 'OAuth expired', needsSignIn: true })).toEqual({
+    reachable: false,
+    error: 'OAuth expired',
+    needsSignIn: true
+  })
+  expect(rosterSourceStatus({ profiles: ['default'], error: 'timed out' }).reachable).toBe(false)
+  expect(rosterSourceStatus({ profiles: ['default'] }).reachable).toBe(true)
+})
diff --git a/apps/desktop/electron/roster-source-status.ts b/apps/desktop/electron/roster-source-status.ts
new file mode 100644
index 0000000000..4cf433c181
--- /dev/null
+++ b/apps/desktop/electron/roster-source-status.ts
@@ -0,0 +1,7 @@
+export function rosterSourceStatus(source: { profiles: string[] | null; error?: string; needsSignIn?: boolean }) {
+  return {
+    reachable: source.profiles !== null && (!source.error || source.error === 'connect-on-demand'),
+    ...(source.error ? { error: source.error } : {}),
+    ...(source.needsSignIn ? { needsSignIn: true } : {})
+  }
+}
diff --git a/apps/desktop/src/app/chat/sidebar/fleet-rail.test.ts b/apps/desktop/src/app/chat/sidebar/fleet-rail.test.ts
index f6b9a11ea9..db226e67fd 100644
--- a/apps/desktop/src/app/chat/sidebar/fleet-rail.test.ts
+++ b/apps/desktop/src/app/chat/sidebar/fleet-rail.test.ts
@@ -95,6 +95,22 @@ describe('buildRestGroups', () => {
     expect(vps?.named).toEqual([])
   })
 
+  it('keeps an expired Cloud source visible but not reachable even with cached profiles', () => {
+    const expired: DesktopAgentRoster = {
+      ...roster,
+      sources: roster.sources.map(source =>
+        source.connectionId === 'pandora'
+          ? { ...source, reachable: false, error: 'OAuth expired', needsSignIn: true }
+          : source
+      )
+    }
+
+    const groups = buildRestGroups({ activeConnectionId: 'local', connections, roster: expired })
+    const cloud = groups.find(group => group.connectionId === 'pandora')
+    expect(cloud).toMatchObject({ reachable: false, error: 'OAuth expired', needsSignIn: true })
+    expect(cloud?.named.map(agent => agent.profile)).toEqual(['omer', 'scout'])
+  })
+
   it('shows every gateway with just its default before the roster has loaded', () => {
     const groups = buildRestGroups({ activeConnectionId: 'pandora', connections, roster: null })
 
diff --git a/apps/desktop/src/app/chat/sidebar/fleet-rail.ts b/apps/desktop/src/app/chat/sidebar/fleet-rail.ts
index ac4b80d043..10de23cfa6 100644
--- a/apps/desktop/src/app/chat/sidebar/fleet-rail.ts
+++ b/apps/desktop/src/app/chat/sidebar/fleet-rail.ts
@@ -22,6 +22,8 @@ export interface FleetGroup {
   kind: DesktopConnectionKind
   label: string
   reachable: boolean
+  error?: string
+  needsSignIn?: boolean
   /** The gateway's default profile — every Hermes home has one, so a group
    *  always carries it even before the roster has been enumerated. */
   defaultAgent: FleetAgent
@@ -94,6 +96,8 @@ export function buildRestGroups({
       kind: connection.kind,
       label: connection.label,
       reachable: source?.reachable ?? true,
+      ...(source?.error && source.error !== 'connect-on-demand' ? { error: source.error } : {}),
+      ...(source?.needsSignIn ? { needsSignIn: true } : {}),
       defaultAgent: toAgent(DEFAULT_PROFILE, defaultRow?.handle),
       named
     })
diff --git a/apps/desktop/src/app/chat/sidebar/profile-switcher.tsx b/apps/desktop/src/app/chat/sidebar/profile-switcher.tsx
index f6d512afc7..20e16d086e 100644
--- a/apps/desktop/src/app/chat/sidebar/profile-switcher.tsx
+++ b/apps/desktop/src/app/chat/sidebar/profile-switcher.tsx
@@ -1180,7 +1180,11 @@ function FleetRestGroup({
 }) {
   const { t } = useI18n()
   const p = t.profiles
-  const dividerLabel = group.reachable ? p.fleet.gateway(group.label) : p.fleet.gatewayUnreachable(group.label)
+
+  const dividerLabel = group.reachable
+    ? p.fleet.gateway(group.label)
+    : `${group.needsSignIn ? `${p.fleet.gateway(group.label)} · ${t.settings.toolsets.needsSignIn}` : p.fleet.gatewayUnreachable(group.label)}${group.error ? `\n${group.error}` : ''}`
+
   const defaultKey = fleetRouteKey(group.connectionId, group.defaultAgent.profile)
   // At rest, This device is a backend switch, not Home. The house glyph stays
   // on the active gateway's default profile.
diff --git a/apps/desktop/src/global.d.ts b/apps/desktop/src/global.d.ts
index b42db8b2f7..91a292e026 100644
--- a/apps/desktop/src/global.d.ts
+++ b/apps/desktop/src/global.d.ts
@@ -1155,6 +1155,7 @@ export interface DesktopAgentRoster {
     kind: DesktopConnectionKind
     reachable: boolean
     error?: string
+    needsSignIn?: boolean
     // Stable backend identity (/api/status install_id) when known.
     installId?: string
   }[]