@@ -111,6 +111,7 @@ function EnvironmentUpdateRow({
   readonly onUpdate: () => void;
 }) {
   const canManageProviders = useEnvironmentScope(group.environmentId, AuthProvidersManageScope);
+  const canUpdateProviders = canManageProviders && group.isReady;
   let trailing: ReactNode;
   switch (status.kind) {
     case "loading":
@@ -122,14 +123,14 @@ function EnvironmentUpdateRow({
     case "failed":
     case "unchanged":
       trailing = (
-        <Button size="xs" variant="outline" disabled={!canManageProviders} onClick={onUpdate}>
+        <Button size="xs" variant="outline" disabled={!canUpdateProviders} onClick={onUpdate}>
           Retry
         </Button>
       );
       break;
     default:
       trailing = (
-        <Button size="xs" variant="outline" disabled={!canManageProviders} onClick={onUpdate}>
+        <Button size="xs" variant="outline" disabled={!canUpdateProviders} onClick={onUpdate}>
           Update
         </Button>
       );
@@ -203,7 +204,7 @@ export function ProviderUpdateEnvironmentRows({
   const handleUpdate = async (environmentId: EnvironmentId) => {
     if (!readEnvironmentScope(environmentId, AuthProvidersManageScope)) return;
     const group = groupByEnvironment.get(environmentId);
-    if (!group || group.candidates.length === 0) {
+    if (!group?.isReady || group.candidates.length === 0) {
       return;
     }
     if (inFlightEnvironmentsRef.current.has(environmentId)) {
 
@@ -447,25 +447,25 @@ describe("provider update launch notification logic", () => {
       ).toBe(true);
     });
 
-    it("waits for a connection before offering cached provider updates", () => {
+    it("keeps the notification key stable while connection readiness changes", () => {
       const cachedProvider = provider({ driver: driver("codex") });
       const primary = environment({
         environmentId: "env-cached",
         isPrimary: true,
         connectionState: "connecting",
         providers: [cachedProvider],
       });
-      const waiting = buildLocalEnvironmentUpdateGroups([primary]);
-      expect(waiting.groups[0]?.candidates).toEqual([]);
-      expect(localEnvironmentUpdateNotificationKey(waiting.groups)).toBeNull();
-
-      const connected = buildLocalEnvironmentUpdateGroups([
-        { ...primary, connectionState: "ready" },
-      ]);
-      expect(connected.groups[0]?.candidates).toEqual([cachedProvider]);
-      expect(localEnvironmentUpdateNotificationKey(connected.groups)).toBe(
-        "env-cached=codex:1.1.0",
-      );
+      for (const connectionState of [
+        "connecting",
+        "ready",
+        "disconnected",
+        "error",
+        "ready",
+      ] as const) {
+        const { groups } = buildLocalEnvironmentUpdateGroups([{ ...primary, connectionState }]);
+        expect(groups[0]?.isReady).toBe(connectionState === "ready");
+        expect(localEnvironmentUpdateNotificationKey(groups)).toBe("env-cached=codex:1.1.0");
+      }
     });
   });
 
@@ -475,6 +475,7 @@ describe("provider update launch notification logic", () => {
       label: "WSL",
       isPrimary: false,
       isSettling: false,
+      isReady: true,
       candidates: [updateCandidate({ driver: driver("codex"), latestVersion: "1.1.0" })],
       providers: [],
     };
 
@@ -737,6 +737,7 @@ export interface LocalEnvironmentUpdateGroup {
   readonly label: string;
   readonly isPrimary: boolean;
   readonly isSettling: boolean;
+  readonly isReady: boolean;
   readonly candidates: ProviderUpdateCandidate[];
   readonly providers: ReadonlyArray<ServerProvider>;
 }
@@ -749,12 +750,10 @@ export function buildLocalEnvironmentUpdateGroups(
     label: environment.label,
     isPrimary: environment.isPrimary,
     isSettling: environment.connectionState === "connecting",
-    candidates:
-      environment.connectionState === "ready"
-        ? collectProviderUpdateCandidates(environment.providers).filter((candidate) =>
-            canOneClickUpdateProviderCandidate(candidate, environment.providers),
-          )
-        : [],
+    isReady: environment.connectionState === "ready",
+    candidates: collectProviderUpdateCandidates(environment.providers).filter((candidate) =>
+      canOneClickUpdateProviderCandidate(candidate, environment.providers),
+    ),
     providers: environment.providers,
   }));
   const isAnySettling = environments.some(