diff --git a/apps/desktop/src/app/settings/gateway-settings.test.ts b/apps/desktop/src/app/settings/gateway-settings.test.ts
new file mode 100644
index 000000000000..a221a4c5acee
--- /dev/null
+++ b/apps/desktop/src/app/settings/gateway-settings.test.ts
@@ -0,0 +1,19 @@
+import { describe, expect, it } from 'vitest'
+
+import { savedCloudConnectionUrl } from './gateway-settings'
+
+describe('savedCloudConnectionUrl', () => {
+  it('normalizes the URL of a persisted cloud connection', () => {
+    expect(savedCloudConnectionUrl({ mode: 'cloud', remoteUrl: ' HTTPS://AGENT.EXAMPLE/ ' })).toBe(
+      'https://agent.example'
+    )
+  })
+
+  it('does not treat a stale cloud URL on a local config as connected', () => {
+    expect(savedCloudConnectionUrl({ mode: 'local', remoteUrl: 'https://agent.example' })).toBe('')
+  })
+
+  it('does not treat a remote gateway URL as a connected cloud agent', () => {
+    expect(savedCloudConnectionUrl({ mode: 'remote', remoteUrl: 'https://agent.example' })).toBe('')
+  })
+})
diff --git a/apps/desktop/src/app/settings/gateway-settings.tsx b/apps/desktop/src/app/settings/gateway-settings.tsx
index 637366f2d605..ca7ce2384f9c 100644
--- a/apps/desktop/src/app/settings/gateway-settings.tsx
+++ b/apps/desktop/src/app/settings/gateway-settings.tsx
@@ -44,6 +44,10 @@ const EMPTY_STATE: GatewaySettingsState = {
   cloudOrg: ''
 }
 
+export function savedCloudConnectionUrl(config: Pick<GatewaySettingsState, 'mode' | 'remoteUrl'>): string {
+  return config.mode === 'cloud' ? config.remoteUrl.trim().replace(/\/+$/, '').toLowerCase() : ''
+}
+
 function ModeCard({
   active,
   description,
@@ -124,6 +128,12 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
   const [state, setState] = useState<GatewaySettingsState>(EMPTY_STATE)
   const [remoteToken, setRemoteToken] = useState('')
   const [lastTest, setLastTest] = useState<null | string>(null)
+  const [connectedCloudUrl, setConnectedCloudUrl] = useState('')
+
+  const acceptSavedConfig = (config: GatewaySettingsState) => {
+    setState(config)
+    setConnectedCloudUrl(savedCloudConnectionUrl(config))
+  }
 
   // --- Hermes Cloud (cloud mode) state ---
   // One portal session powers discovery + the silent per-agent cascade. These
@@ -191,7 +201,7 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
           return
         }
 
-        setState(config)
+        acceptSavedConfig(config)
       })
       .catch(err => notifyError(err, g.failedLoad))
       .finally(() => {
@@ -220,7 +230,6 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
   // (trim, drop trailing slash, lowercase) or a host-casing difference would
   // silently break the connected-highlight.
   const normalizeCloudUrl = (url: string) => url.trim().replace(/\/+$/, '').toLowerCase()
-  const connectedCloudUrl = state.mode === 'cloud' ? normalizeCloudUrl(state.remoteUrl) : ''
 
   const isConnectedAgent = (agent: DesktopCloudAgent) =>
     Boolean(connectedCloudUrl && agent.dashboardUrl && normalizeCloudUrl(agent.dashboardUrl) === connectedCloudUrl)
@@ -368,7 +377,7 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
         ? await window.hermesDesktop.applyConnectionConfig(payload())
         : await window.hermesDesktop.saveConnectionConfig(payload())
 
-      setState(next)
+      acceptSavedConfig(next)
       setRemoteToken('')
       notify({
         kind: 'success',
@@ -404,13 +413,13 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
         remoteUrl: trimmedUrl
       })
 
-      setState(saved)
+      acceptSavedConfig(saved)
 
       const result = await window.hermesDesktop.oauthLoginConnectionConfig(trimmedUrl)
 
       if (result.connected) {
         const refreshed = await window.hermesDesktop.getConnectionConfig(scope)
-        setState(refreshed)
+        acceptSavedConfig(refreshed)
         notify({ kind: 'success', title: g.signedIn, message: g.connectedTo(providerLabel) })
       } else {
         notify({
@@ -432,7 +441,7 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
     try {
       await window.hermesDesktop.oauthLogoutConnectionConfig(trimmedUrl || undefined)
       const refreshed = await window.hermesDesktop.getConnectionConfig(scope)
-      setState(refreshed)
+      acceptSavedConfig(refreshed)
       notify({ kind: 'success', title: g.signedOutTitle, message: g.signedOutMessage })
     } catch (err) {
       notifyError(err, g.signOutFailed)
@@ -656,7 +665,7 @@ export function GatewaySettings({ embedded = false }: { embedded?: boolean } = {
         cloudOrg: cloudOrgRef.current ?? undefined
       })
 
-      setState(next)
+      acceptSavedConfig(next)
       notify({ kind: 'success', title: g.cloudConnectedTitle, message: g.cloudConnectedTo(agent.name) })
     } catch (err) {
       if (err && typeof err === 'object' && 'needsCloudLogin' in err) {