diff --git a/apps/desktop/src/app/settings/providers-settings.terminal-disconnect.test.tsx b/apps/desktop/src/app/settings/providers-settings.terminal-disconnect.test.tsx
new file mode 100644
index 0000000000..bb69419856
--- /dev/null
+++ b/apps/desktop/src/app/settings/providers-settings.terminal-disconnect.test.tsx
@@ -0,0 +1,120 @@
+import { act, cleanup, fireEvent, render, screen, waitFor } from '@testing-library/react'
+import { atom } from 'nanostores'
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+
+import { ConfirmHost } from '@/components/confirm-host'
+import { $confirmRequest } from '@/store/confirm'
+import type { OAuthProvider } from '@/types/hermes'
+
+const listOAuthProviders = vi.fn()
+const disconnectOAuthProvider = vi.fn()
+const startManualProviderOAuth = vi.fn()
+const runInTerminal = vi.fn()
+const notify = vi.fn()
+const notifyError = vi.fn()
+
+vi.mock('@/hermes', () => ({
+  setApiRequestProfile: vi.fn(),
+  getProfiles: async () => ({ profiles: [] }),
+  disconnectOAuthProvider: (...args: unknown[]) => disconnectOAuthProvider(...args),
+  getEnvVars: async () => ({}),
+  listOAuthProviders: (...args: unknown[]) => listOAuthProviders(...args)
+}))
+
+vi.mock('@/store/onboarding', () => ({
+  $desktopOnboarding: atom({ manual: false }),
+  startManualProviderOAuth: (...args: unknown[]) => startManualProviderOAuth(...args),
+  startManualLocalEndpoint: vi.fn()
+}))
+
+vi.mock('@/app/right-sidebar/store', () => ({
+  runInTerminal: (command: string) => runInTerminal(command)
+}))
+
+vi.mock('@/store/notifications', () => ({
+  notify: (notification: unknown) => notify(notification),
+  notifyError: (...args: unknown[]) => notifyError(...args)
+}))
+
+const COMMAND = 'Remove-Item -LiteralPath "$HOME/.external/credentials.json" -Force -ErrorAction Stop'
+
+function connectedExternal(patch: Partial<OAuthProvider> = {}): OAuthProvider {
+  return {
+    cli_command: 'external login',
+    disconnect_command: COMMAND,
+    disconnectable: false,
+    docs_url: '',
+    flow: 'external',
+    id: 'external-cli',
+    name: 'External CLI',
+    status: { logged_in: true },
+    ...patch
+  }
+}
+
+beforeEach(() => {
+  listOAuthProviders.mockResolvedValue({ providers: [connectedExternal()] })
+  disconnectOAuthProvider.mockResolvedValue({ ok: false, provider: 'nous' })
+  Object.defineProperty(window, 'hermesDesktop', {
+    configurable: true,
+    value: { terminal: {} }
+  })
+})
+
+afterEach(() => {
+  cleanup()
+  $confirmRequest.set(null)
+  vi.clearAllMocks()
+})
+
+async function renderAccounts() {
+  const { ProvidersSettings } = await import('./providers-settings')
+
+  await act(async () => {
+    render(
+      <>
+        <ProvidersSettings onClose={vi.fn()} onViewChange={vi.fn()} view="accounts" />
+        <ConfirmHost />
+      </>
+    )
+  })
+}
+
+describe('connected external provider row', () => {
+  it('runs the terminal control as disconnect instead of starting sign-in', async () => {
+    await renderAccounts()
+
+    fireEvent.click(await screen.findByRole('button', { name: /Disconnect External CLI in terminal/ }))
+    fireEvent.click(await screen.findByRole('button', { name: 'Disconnect' }))
+
+    await waitFor(() => expect(runInTerminal).toHaveBeenCalledWith(COMMAND))
+    expect(startManualProviderOAuth).not.toHaveBeenCalled()
+    expect(notify).not.toHaveBeenCalledWith(expect.objectContaining({ kind: 'success' }))
+    expect(notify).not.toHaveBeenCalledWith(expect.objectContaining({ title: 'Account removed' }))
+  })
+
+  it('does not toast success when an API clear reports nothing was removed', async () => {
+    listOAuthProviders.mockResolvedValue({
+      providers: [
+        {
+          cli_command: 'hermes auth add nous',
+          disconnectable: true,
+          docs_url: '',
+          flow: 'device_code',
+          id: 'nous',
+          name: 'Nous Portal',
+          status: { logged_in: true }
+        }
+      ]
+    })
+
+    await renderAccounts()
+    fireEvent.click(await screen.findByRole('button', { name: 'Remove Nous Portal' }))
+    fireEvent.click(await screen.findByRole('button', { name: 'Disconnect' }))
+
+    await waitFor(() => expect(disconnectOAuthProvider).toHaveBeenCalled())
+    expect(notify).not.toHaveBeenCalledWith(expect.objectContaining({ kind: 'success' }))
+    expect(notify).not.toHaveBeenCalledWith(expect.objectContaining({ title: 'Account removed' }))
+    expect(notifyError).toHaveBeenCalled()
+  })
+})
diff --git a/apps/desktop/src/app/settings/providers-settings.tsx b/apps/desktop/src/app/settings/providers-settings.tsx
index c31e047137..58b831c8de 100644
--- a/apps/desktop/src/app/settings/providers-settings.tsx
+++ b/apps/desktop/src/app/settings/providers-settings.tsx
@@ -260,7 +260,10 @@ function ConnectedProviderRow({
 
   return (
     <div className="group grid grid-cols-[minmax(0,1fr)_auto] items-center gap-1 rounded-[6px] transition-colors hover:bg-(--ui-control-hover-background)">
-      <RowButton className="min-w-0 px-3 py-2.5 text-left" onClick={() => onSelect(provider)}>
+      <RowButton
+        className="min-w-0 px-3 py-2.5 text-left"
+        onClick={() => (terminalDisconnect ? onTerminalDisconnect(provider) : onSelect(provider))}
+      >
         <div className="flex min-w-0 items-center gap-2">
           <span className="truncate text-[length:var(--conversation-text-font-size)] font-semibold">{title}</span>
           <span className="inline-flex shrink-0 items-center gap-1 bg-primary/10 px-2 py-0.5 text-xs font-medium text-primary">
@@ -276,7 +279,20 @@ function ConnectedProviderRow({
         )}
       </RowButton>
       <div className="flex items-center gap-1 pr-2">
-        <Trail className="size-4 text-muted-foreground transition group-hover:text-foreground" />
+        {terminalDisconnect ? (
+          <Button
+            aria-label={`${copy.disconnect} ${title} in terminal`}
+            onClick={() => onTerminalDisconnect(provider)}
+            size="icon-xs"
+            title={copy.disconnectInTerminal}
+            type="button"
+            variant="ghost"
+          >
+            <Terminal className="size-4" />
+          </Button>
+        ) : (
+          <Trail className="size-4 text-muted-foreground transition group-hover:text-foreground" />
+        )}
         {canDisconnect && (
           <Button
             aria-label={`${t.common.remove} ${title}`}
@@ -423,7 +439,7 @@ export function ProvidersSettings({
     runInTerminal(command)
     notify({
       kind: 'info',
-      title: t.settings.providers.removedTitle,
+      title: t.settings.providers.disconnect,
       message: t.settings.providers.removeTerminalRunning(name)
     })
   }
@@ -444,7 +460,13 @@ export function ProvidersSettings({
     setDisconnecting(provider.id)
 
     try {
-      await disconnectOAuthProvider(provider.id, scopeProfile)
+      const result = await disconnectOAuthProvider(provider.id, scopeProfile)
+
+      if (!result?.ok) {
+        notifyError(new Error('No stored credentials were removed'), t.settings.providers.failedRemove(name))
+        return
+      }
+
       notify({
         durationMs: 3_000,
         kind: 'success',
diff --git a/hermes_cli/web_routers/oauth.py b/hermes_cli/web_routers/oauth.py
index ad7e8da787..ba2b0b63bf 100644
--- a/hermes_cli/web_routers/oauth.py
+++ b/hermes_cli/web_routers/oauth.py
@@ -559,20 +559,39 @@ async def _start_device_code_flow(provider_id: str, profile: Optional[str] = Non
     return await starter(profile)
 
 
-def _oauth_provider_disconnect_command(provider: Dict[str, Any]) -> Optional[str]:
+def _claude_code_disconnect_command(platform: str) -> str:
+    """Host-native command that removes Claude Code's borrowed credential file.
+
+    Windows must not emit ``rm -f``. PowerShell aliases ``rm`` to ``Remove-Item``,
+    and ``-f`` binds both ``-Force`` and ``-Filter`` (AmbiguousParameter).
+    """
+    if platform == "win32":
+        literal = '"$HOME/.claude/.credentials.json"'
+        return (
+            f"if (Test-Path -LiteralPath {literal}) {{ "
+            f"Remove-Item -LiteralPath {literal} -Force -ErrorAction Stop }}"
+        )
+    rm_file = "rm -f ~/.claude/.credentials.json"
+    if platform == "darwin":
+        return f'security delete-generic-password -s "Claude Code-credentials" 2>/dev/null; {rm_file}'
+    return rm_file
+
+
+def _oauth_provider_disconnect_command(
+    provider: Dict[str, Any], platform: Optional[str] = None
+) -> Optional[str]:
     """Shell command that clears an external provider's credentials, or None.
 
     The disconnect API never silently deletes files another CLI owns; the GUI runs
     this in its embedded terminal so the user sees exactly what executes. Claude Code
     has no scriptable logout, so remove what logout would: the macOS Keychain entry
     and/or ``~/.claude/.credentials.json`` (the two ``read_claude_code_credentials()`` sources).
+    ``platform`` is the host the command will run on (default: this process). Pass it
+    explicitly in tests; do not fake ``sys.platform``.
     """
     if provider.get("flow") != "external" or provider.get("id") != "claude-code":
         return None
-    rm_file = "rm -f ~/.claude/.credentials.json"
-    if sys.platform == "darwin":
-        return f'security delete-generic-password -s "Claude Code-credentials" 2>/dev/null; {rm_file}'
-    return rm_file
+    return _claude_code_disconnect_command(platform or sys.platform)
 
 
 def _oauth_provider_disconnect_hint(provider: Dict[str, Any], status: Dict[str, Any]) -> Optional[str]:
@@ -653,15 +672,25 @@ def _clear_anthropic_auth() -> bool:
             oauth_file.unlink()
             cleared = True
     except Exception:
-        pass
+        _log.exception("disconnect anthropic OAuth file failed")
+        raise
     try:
         from hermes_cli.auth import clear_provider_auth
         cleared = clear_provider_auth("anthropic") or cleared
     except Exception:
-        pass
+        _log.exception("disconnect anthropic auth store failed")
+        raise
     return cleared
 
 
+def _disconnect_http_error(status_code: int, provider_name: str) -> HTTPException:
+    if status_code == 409:
+        detail = f"No stored credentials were removed for {provider_name}."
+    else:
+        detail = f"Failed to remove stored credentials for {provider_name}."
+    return HTTPException(status_code=status_code, detail=detail)
+
+
 @router.delete("/api/providers/oauth/{provider_id}")
 async def disconnect_oauth_provider(provider_id: str, request: Request, profile: Optional[str] = None):
     """Disconnect an OAuth provider. Token-protected (matches /env/reveal)."""
@@ -677,19 +706,31 @@ async def disconnect_oauth_provider(provider_id: str, request: Request, profile:
         _reject_if_not_disconnectable(provider, _resolve_provider_status(provider_id, provider.get("status_fn")))
 
         if provider_id == "anthropic":
-            cleared = _clear_anthropic_auth()
+            try:
+                cleared = _clear_anthropic_auth()
+            except HTTPException:
+                raise
+            except Exception:
+                _log.exception("disconnect %s failed", provider_id)
+                raise _disconnect_http_error(500, provider["name"])
+            if not cleared:
+                raise _disconnect_http_error(409, provider["name"])
             _log.info("oauth/disconnect: %s", provider_id)
-            return {"ok": bool(cleared), "provider": provider_id}
+            return {"ok": True, "provider": provider_id}
         try:
             from hermes_cli.auth import clear_provider_auth, invalidate_nous_auth_status_cache
             cleared = clear_provider_auth(provider_id)
             if provider_id == "nous":
                 invalidate_nous_auth_status_cache()
+            if not cleared:
+                raise _disconnect_http_error(409, provider["name"])
             _log.info("oauth/disconnect: %s (cleared=%s)", provider_id, cleared)
-            return {"ok": bool(cleared), "provider": provider_id}
-        except Exception as e:
+            return {"ok": True, "provider": provider_id}
+        except HTTPException:
+            raise
+        except Exception:
             _log.exception("disconnect %s failed", provider_id)
-            raise HTTPException(status_code=500, detail=str(e))
+            raise _disconnect_http_error(500, provider["name"])
 
     return await scoped_to_thread(profile, _run)
 
diff --git a/hermes_cli/web_server_oauth.py b/hermes_cli/web_server_oauth.py
index 78510ff777..6752df1716 100644
--- a/hermes_cli/web_server_oauth.py
+++ b/hermes_cli/web_server_oauth.py
@@ -74,14 +74,21 @@ def _anthropic_oauth_status() -> Dict[str, Any]:
 
 
 def _claude_code_only_status() -> Dict[str, Any]:
-    """Claude Code CLI credentials as their own entry, independent of the Anthropic card."""
+    """Claude Code CLI credentials as their own entry, independent of the Anthropic card.
+
+    Connected follows the same local validity gate as Anthropic resolution. A
+    persisted access token that has already expired is not a usable login.
+    """
     try:
-        from agent.anthropic_credentials import read_claude_code_credentials
+        from agent.anthropic_credentials import (
+            is_claude_code_token_valid,
+            read_claude_code_credentials,
+        )
         creds = read_claude_code_credentials()
+        if creds and is_claude_code_token_valid(creds):
+            return _token_status("claude_code_cli", "~/.claude/.credentials.json", creds)
     except Exception:
-        creds = None
-    if creds and creds.get("accessToken"):
-        return _token_status("claude_code_cli", "~/.claude/.credentials.json", creds)
+        pass
     return dict(_LOGGED_OUT)
 
 
diff --git a/tests/hermes_cli/test_claude_code_account_connection.py b/tests/hermes_cli/test_claude_code_account_connection.py
new file mode 100644
index 0000000000..2df475cb74
--- /dev/null
+++ b/tests/hermes_cli/test_claude_code_account_connection.py
@@ -0,0 +1,69 @@
+"""Accounts Connected must follow Claude Code token validity, not token presence."""
+
+from hermes_cli.web_server import _SESSION_TOKEN, app
+from fastapi.testclient import TestClient
+
+client = TestClient(app)
+HEADERS = {"X-Hermes-Session-Token": _SESSION_TOKEN}
+
+
+def test_expired_claude_code_token_is_not_connected(monkeypatch):
+    """A present but expired access token must not mark the account Connected."""
+    from agent import anthropic_credentials
+
+    monkeypatch.setattr(
+        anthropic_credentials,
+        "read_claude_code_credentials",
+        lambda: {"accessToken": "stale-token", "expiresAt": 1},
+    )
+
+    resp = client.get("/api/providers/oauth", headers=HEADERS)
+    assert resp.status_code == 200, resp.text
+    providers = {p["id"]: p for p in resp.json()["providers"]}
+
+    assert providers["claude-code"]["status"]["logged_in"] is False
+
+
+def test_windows_claude_code_removal_command_is_unambiguous_powershell():
+    """PowerShell must not see ``rm -f``: ``-f`` is an ambiguous Remove-Item parameter."""
+    from hermes_cli.web_routers.oauth import _oauth_provider_disconnect_command
+
+    command = _oauth_provider_disconnect_command(
+        {"id": "claude-code", "flow": "external"}, platform="win32"
+    )
+
+    assert command is not None
+    assert "Remove-Item" in command
+    assert "-LiteralPath" in command
+    assert "-Force" in command
+    assert "rm -f" not in command
+    assert " -f " not in command and not command.strip().endswith(" -f")
+
+
+def test_disconnect_is_not_success_when_nothing_was_cleared(monkeypatch):
+    """A no-op clear must not be a 200 the client can toast as removed."""
+    from hermes_cli import auth as auth_mod
+
+    monkeypatch.setattr(auth_mod, "clear_provider_auth", lambda _provider: False)
+
+    resp = client.delete("/api/providers/oauth/nous", headers=HEADERS)
+
+    assert resp.status_code == 409, resp.text
+    assert resp.json().get("ok") is not True
+
+
+def test_disconnect_failure_does_not_echo_the_store_error(monkeypatch):
+    from hermes_cli import auth as auth_mod
+
+    secret = "auth store is read-only: /secret/hermes-home"
+
+    def fail_clear(_provider):
+        raise OSError(secret)
+
+    monkeypatch.setattr(auth_mod, "clear_provider_auth", fail_clear)
+
+    resp = client.delete("/api/providers/oauth/nous", headers=HEADERS)
+
+    assert resp.status_code == 500, resp.text
+    assert secret not in resp.text
+