diff --git a/apps/desktop/electron/main.cjs b/apps/desktop/electron/main.cjs
index d47e2403eaaa..922b7b2b8db1 100644
--- a/apps/desktop/electron/main.cjs
+++ b/apps/desktop/electron/main.cjs
@@ -4815,7 +4815,20 @@ async function discoverCloudAgents(org) {
     throw error
   }
 
-  return { agents: trimCloudAgents(body) }
+  return { agents: trimCloudAgents(body), org: trimCloudOrg(body?.org) }
+}
+
+// Project a NAS response org ({ id, slug, name, isPersonal }) to the trimmed
+// shape the renderer persists, or null when absent/malformed.
+function trimCloudOrg(org) {
+  if (!org || typeof org !== 'object' || typeof org.id !== 'string') return null
+  return {
+    id: org.id,
+    slug: typeof org.slug === 'string' ? org.slug : null,
+    name: typeof org.name === 'string' ? org.name : org.id,
+    isPersonal: Boolean(org.isPersonal),
+    role: typeof org.role === 'string' ? org.role : 'MEMBER'
+  }
 }
 
 // Extract the org list from a 409 org_selection_required error body. The error
@@ -4933,6 +4946,14 @@ function sanitizeConnectionProfiles(raw) {
     if (entry.token && typeof entry.token === 'object') {
       cleaned.token = entry.token
     }
+    // Preserve the Hermes Cloud org tag on cloud-mode entries so Settings can
+    // reopen into the same org for a per-profile cloud connection.
+    if (cleaned.mode === 'cloud') {
+      const org = String(entry.org || '').trim()
+      if (org) {
+        cleaned.org = org
+      }
+    }
     out[name] = cleaned
   }
 
@@ -5064,6 +5085,9 @@ async function sanitizeDesktopConnectionConfig(config = readDesktopConnectionCon
     remoteAuthMode: authMode,
     remoteOauthConnected,
     remoteUrl,
+    // The persisted Hermes Cloud org (slug/id) for a cloud connection, or '' for
+    // remote/local. Lets Settings → Gateway reopen into the same org.
+    cloudOrg: mode === 'cloud' ? String(block.org || '') : '',
     remoteTokenPreview: tokenPreview(remoteToken),
     remoteTokenSet: Boolean(remoteToken),
     // The env override only forces the global/primary connection; a per-profile
@@ -5075,11 +5099,19 @@ async function sanitizeDesktopConnectionConfig(config = readDesktopConnectionCon
 // Build + validate a `{ url, authMode, token }` remote block. OAuth gateways
 // authenticate via the login-window session cookie (verified at connect time in
 // resolveRemoteBackend), so only token-auth remotes require a saved token.
-function buildRemoteBlock(remoteUrl, authMode, token) {
+// `org` (optional) is the Hermes Cloud org slug/id the instance was discovered
+// under — persisted so Settings can reopen into the same org; omitted from the
+// block when empty so plain remote connections stay unchanged.
+function buildRemoteBlock(remoteUrl, authMode, token, org) {
   if (authMode !== 'oauth' && !decryptDesktopSecret(token)) {
     throw new Error('Remote gateway session token is required.')
   }
-  return { url: normalizeRemoteBaseUrl(remoteUrl), authMode, token }
+  const block = { url: normalizeRemoteBaseUrl(remoteUrl), authMode, token }
+  const orgValue = typeof org === 'string' ? org.trim() : ''
+  if (orgValue) {
+    block.org = orgValue
+  }
+  return block
 }
 
 function coerceDesktopConnectionConfig(input = {}, existing = readDesktopConnectionConfig(), options = {}) {
@@ -5096,6 +5128,11 @@ function coerceDesktopConnectionConfig(input = {}, existing = readDesktopConnect
   const remoteUrl = String(input.remoteUrl ?? existingBlock.url ?? '').trim()
   // authMode: explicit input wins; otherwise inherit the saved value, default 'token'.
   const authMode = resolveAuthMode(input.remoteAuthMode, existingBlock.authMode)
+  // Cloud org: only meaningful for 'cloud' mode. Explicit input wins; otherwise
+  // inherit the saved org. A plain 'remote' connection never carries an org
+  // (switching cloud→remote drops it), so it stays unset unless mode is cloud.
+  const cloudOrg =
+    mode === 'cloud' ? String(input.cloudOrg ?? existingBlock.org ?? '').trim() : ''
   const incomingToken = typeof input.remoteToken === 'string' ? input.remoteToken.trim() : ''
   const nextToken = incomingToken
     ? persistToken
@@ -5109,7 +5146,7 @@ function coerceDesktopConnectionConfig(input = {}, existing = readDesktopConnect
     // default. The mode tag (remote vs cloud) is preserved on the entry.
     const profiles = { ...(existing.profiles || {}) }
     if (remoteLike) {
-      profiles[key] = { mode, ...buildRemoteBlock(remoteUrl, authMode, nextToken) }
+      profiles[key] = { mode, ...buildRemoteBlock(remoteUrl, authMode, nextToken, cloudOrg) }
     } else {
       delete profiles[key]
     }
@@ -5121,7 +5158,7 @@ function coerceDesktopConnectionConfig(input = {}, existing = readDesktopConnect
   }
 
   const nextRemote = remoteLike
-    ? buildRemoteBlock(remoteUrl, authMode, nextToken)
+    ? buildRemoteBlock(remoteUrl, authMode, nextToken, cloudOrg)
     : { url: remoteUrl ? normalizeRemoteBaseUrl(remoteUrl) : remoteUrl, authMode, token: nextToken }
 
   // Preserve per-profile overrides when saving the global connection.
diff --git a/apps/desktop/src/app/settings/gateway-settings.tsx b/apps/desktop/src/app/settings/gateway-settings.tsx
index 0130dab6cc1f..44b363425682 100644
--- a/apps/desktop/src/app/settings/gateway-settings.tsx
+++ b/apps/desktop/src/app/settings/gateway-settings.tsx
@@ -33,6 +33,7 @@ interface GatewaySettingsState {
   remoteTokenPreview: string | null
   remoteTokenSet: boolean
   remoteUrl: string
+  cloudOrg: string
 }
 
 const EMPTY_STATE: GatewaySettingsState = {
@@ -42,7 +43,8 @@ const EMPTY_STATE: GatewaySettingsState = {
   remoteOauthConnected: false,
   remoteTokenPreview: null,
   remoteTokenSet: false,
-  remoteUrl: ''
+  remoteUrl: '',
+  cloudOrg: ''
 }
 
 function ModeCard({
@@ -186,6 +188,21 @@ export function GatewaySettings() {
   // OAuth login button or the session-token entry box. The effective auth mode
   // prefers a fresh probe result over the saved value.
   const trimmedUrl = state.remoteUrl.trim()
+
+  // The dashboardUrl of the currently-connected cloud instance (the saved
+  // cloud connection's remoteUrl), normalized for comparison against each
+  // discovered agent's dashboardUrl so we can highlight the active one and hide
+  // its Connect button. Empty unless the saved connection is a cloud one.
+  const connectedCloudUrl =
+    state.mode === 'cloud' ? state.remoteUrl.trim().replace(/\/+$/, '') : ''
+
+  const isConnectedAgent = (agent: DesktopCloudAgent) =>
+    Boolean(
+      connectedCloudUrl &&
+        agent.dashboardUrl &&
+        agent.dashboardUrl.trim().replace(/\/+$/, '') === connectedCloudUrl
+    )
+
   useEffect(() => {
     if (state.mode !== 'remote' || !trimmedUrl || !/^https?:\/\//i.test(trimmedUrl)) {
       setProbeStatus('idle')
@@ -433,7 +450,16 @@ export function GatewaySettings() {
       // Single org (or org now chosen): we have agents.
       setCloudAgents('agents' in result ? result.agents : [])
 
-      if (org) {
+      // Record the org AUTHORITATIVELY from the response (NAS echoes the org the
+      // list was scoped to), falling back to the org we requested. This is what
+      // gets persisted on connect, so it must be set even on single-membership
+      // auto-resolve where no picker ran and no `org` arg was passed.
+      const resolvedOrgRef =
+        'org' in result && result.org ? (result.org.slug ?? result.org.id) : null
+
+      if (resolvedOrgRef) {
+        setCloudOrg(resolvedOrgRef)
+      } else if (org) {
         setCloudOrg(org)
       }
 
@@ -483,7 +509,17 @@ export function GatewaySettings() {
         setCloudSignedIn(status.signedIn)
 
         if (status.signedIn) {
-          void discoverCloud()
+          // Restore the persisted org (if any) so we reopen straight into that
+          // org's agent list instead of the picker; discoverCloud(org) also
+          // records it as the selected org. Empty → normal discovery (single-org
+          // resolves automatically; multi-org shows the picker).
+          const savedOrg = state.cloudOrg || ''
+
+          if (savedOrg) {
+            setCloudOrg(savedOrg)
+          }
+
+          void discoverCloud(savedOrg || undefined)
         } else {
           setCloudAgents([])
           setCloudOrgs([])
@@ -578,11 +614,13 @@ export function GatewaySettings() {
       }
 
       // Persist a cloud-mode connection (remote-shaped, oauth) and reconnect.
+      // Include the selected org so Settings reopens into the same org + instance.
       const next = await desktop.applyConnectionConfig({
         mode: 'cloud',
         profile: scope ?? undefined,
         remoteAuthMode: 'oauth',
-        remoteUrl: agent.dashboardUrl
+        remoteUrl: agent.dashboardUrl,
+        cloudOrg: cloudOrg ?? undefined
       })
 
       setState(next)
@@ -806,27 +844,45 @@ export function GatewaySettings() {
                 </div>
               ) : (
                 <div className="grid gap-1">
-                  {cloudAgents.map(agent => (
-                    <ListRow
-                      action={
-                        <Button
-                          disabled={!agent.dashboardUrl || cloudConnectingId !== null}
-                          onClick={() => void connectCloudAgent(agent)}
-                          size="sm"
-                        >
-                          {cloudConnectingId === agent.id ? <Loader2 className="animate-spin" /> : null}
-                          {agent.dashboardUrl
-                            ? cloudConnectingId === agent.id
-                              ? g.cloudConnecting
-                              : g.cloudConnect
-                            : g.cloudAgentProvisioning}
-                        </Button>
-                      }
-                      description={g.cloudStatusLabel(agent.dashboardGatewayState)}
-                      key={agent.id}
-                      title={agent.name}
-                    />
-                  ))}
+                  {cloudAgents.map(agent => {
+                    const connected = isConnectedAgent(agent)
+
+                    return (
+                      <div
+                        className={cn(
+                          'rounded-md px-2',
+                          connected && 'bg-primary/5 ring-1 ring-primary/25'
+                        )}
+                        key={agent.id}
+                      >
+                        <ListRow
+                          action={
+                            connected ? (
+                              <Pill tone="primary">
+                                <Check className="mr-1 inline size-3" />
+                                {g.cloudConnectedPill}
+                              </Pill>
+                            ) : (
+                              <Button
+                                disabled={!agent.dashboardUrl || cloudConnectingId !== null}
+                                onClick={() => void connectCloudAgent(agent)}
+                                size="sm"
+                              >
+                                {cloudConnectingId === agent.id ? <Loader2 className="animate-spin" /> : null}
+                                {agent.dashboardUrl
+                                  ? cloudConnectingId === agent.id
+                                    ? g.cloudConnecting
+                                    : g.cloudConnect
+                                  : g.cloudAgentProvisioning}
+                              </Button>
+                            )
+                          }
+                          description={g.cloudStatusLabel(agent.dashboardGatewayState)}
+                          title={agent.name}
+                        />
+                      </div>
+                    )
+                  })}
                 </div>
               )}
             </div>
diff --git a/apps/desktop/src/components/boot-failure-reauth.test.ts b/apps/desktop/src/components/boot-failure-reauth.test.ts
index cb55cd6772c6..bf6f4f7ab91f 100644
--- a/apps/desktop/src/components/boot-failure-reauth.test.ts
+++ b/apps/desktop/src/components/boot-failure-reauth.test.ts
@@ -14,6 +14,7 @@ function config(overrides: Partial<DesktopConnectionConfig> = {}): DesktopConnec
     remoteTokenPreview: null,
     remoteTokenSet: false,
     remoteUrl: 'https://box:9119',
+    cloudOrg: '',
     ...overrides
   }
 }
diff --git a/apps/desktop/src/global.d.ts b/apps/desktop/src/global.d.ts
index cf5089392f56..751103c3a5ad 100644
--- a/apps/desktop/src/global.d.ts
+++ b/apps/desktop/src/global.d.ts
@@ -412,6 +412,10 @@ export interface DesktopConnectionConfig {
   remoteTokenPreview: string | null
   remoteTokenSet: boolean
   remoteUrl: string
+  // For a 'cloud' connection: the persisted Hermes Cloud org (slug or id) the
+  // connected instance was discovered under, so Settings → Gateway can reopen
+  // into that org. Empty string for remote/local.
+  cloudOrg: string
 }
 
 export interface DesktopConnectionConfigInput {
@@ -422,6 +426,9 @@ export interface DesktopConnectionConfigInput {
   remoteAuthMode?: 'oauth' | 'token'
   remoteToken?: string
   remoteUrl?: string
+  // For a 'cloud' connection: the selected Hermes Cloud org (slug or id) to
+  // persist so Settings can reopen into it. Ignored for remote/local modes.
+  cloudOrg?: string
 }
 
 export interface DesktopConnectionTestResult {
@@ -493,9 +500,11 @@ export interface DesktopCloudOrg {
 
 // Discovery result: either the agent list, OR a request to pick an org first
 // (multi-org user, no org chosen yet). The renderer shows a picker on the
-// latter and re-calls discover(org).
+// latter and re-calls discover(org). On the agents branch, `org` echoes the
+// authoritatively-resolved org the list was scoped to (from NAS), so the
+// desktop persists it without relying on transient picker state.
 export type DesktopCloudDiscoverResult =
-  | { agents: DesktopCloudAgent[]; needsOrgSelection?: false }
+  | { agents: DesktopCloudAgent[]; org?: DesktopCloudOrg | null; needsOrgSelection?: false }
   | { needsOrgSelection: true; orgs: DesktopCloudOrg[] }
 
 export interface DesktopCloudAgentSignInResult {
diff --git a/apps/desktop/src/i18n/en.ts b/apps/desktop/src/i18n/en.ts
index d0bbdb6e9fde..65de41a688e1 100644
--- a/apps/desktop/src/i18n/en.ts
+++ b/apps/desktop/src/i18n/en.ts
@@ -558,6 +558,7 @@ export const en: Translations = {
       cloudSignedOutTitle: 'Signed out of Hermes Cloud',
       cloudSignedOutMessage: 'Cleared the Hermes Cloud session.',
       cloudConnectedTitle: 'Connected',
+      cloudConnectedPill: 'Connected',
       cloudConnectedTo: name => `Connected to ${name}.`,
       cloudAgentProvisioning: 'Provisioning…',
       cloudStatusLabel: status => `Status: ${status}`,
diff --git a/apps/desktop/src/i18n/types.ts b/apps/desktop/src/i18n/types.ts
index 2d3e3d4bc121..39f990dcfca2 100644
--- a/apps/desktop/src/i18n/types.ts
+++ b/apps/desktop/src/i18n/types.ts
@@ -465,6 +465,7 @@ export interface Translations {
       cloudSignedOutTitle: string
       cloudSignedOutMessage: string
       cloudConnectedTitle: string
+      cloudConnectedPill: string
       cloudConnectedTo: (name: string) => string
       cloudAgentProvisioning: string
       cloudStatusLabel: (status: string) => string
diff --git a/apps/desktop/src/i18n/zh.ts b/apps/desktop/src/i18n/zh.ts
index 9af001ba7369..295a6aaf9c1c 100644
--- a/apps/desktop/src/i18n/zh.ts
+++ b/apps/desktop/src/i18n/zh.ts
@@ -747,6 +747,7 @@ export const zh: Translations = {
       cloudSignedOutTitle: '已退出 Hermes Cloud',
       cloudSignedOutMessage: '已清除 Hermes Cloud 会话。',
       cloudConnectedTitle: '已连接',
+      cloudConnectedPill: '已连接',
       cloudConnectedTo: name => `已连接到 ${name}。`,
       cloudAgentProvisioning: '正在配置…',
       cloudStatusLabel: status => `状态：${status}`,