diff --git a/apps/desktop/src/updates/DesktopUpdates.test.ts b/apps/desktop/src/updates/DesktopUpdates.test.ts
index 2a0d1d453092..94bfbe44c368 100644
--- a/apps/desktop/src/updates/DesktopUpdates.test.ts
+++ b/apps/desktop/src/updates/DesktopUpdates.test.ts
@@ -107,6 +107,29 @@ describe("DesktopUpdates", () => {
     }),
   );
 
+  it.effect("keeps the disabled reason available after configuration and channel changes", () => {
+    const harness = makeHarness({ env: { T3CODE_DISABLE_AUTO_UPDATE: "true" } });
+    const reason = "Automatic updates are disabled by the T3CODE_DISABLE_AUTO_UPDATE setting.";
+
+    return Effect.scoped(
+      Effect.gen(function* () {
+        const updates = yield* DesktopUpdates.DesktopUpdates;
+        yield* updates.configure;
+
+        const configured = yield* updates.getState;
+        assert.equal(configured.message, reason);
+
+        const changed = yield* updates.setChannel("nightly");
+        assert.equal(changed.channel, "nightly");
+        assert.equal(changed.enabled, false);
+        assert.equal(changed.status, "disabled");
+        assert.equal(changed.message, reason);
+        assert.equal(harness.sentStates.at(-1)?.message, reason);
+        assert.equal(harness.checkCount(), 0);
+      }),
+    ).pipe(Effect.provide(harness.layer));
+  });
+
   it.effect("subscribe delivers the latest state plus subsequent changes", () => {
     const harness = makeHarness();
 
diff --git a/apps/desktop/src/updates/DesktopUpdates.ts b/apps/desktop/src/updates/DesktopUpdates.ts
index b2d93f407ac7..ae3c2588fab2 100644
--- a/apps/desktop/src/updates/DesktopUpdates.ts
+++ b/apps/desktop/src/updates/DesktopUpdates.ts
@@ -273,13 +273,15 @@ function parseAppUpdateYml(raw: string): Effect.Effect<Option.Option<AppUpdateYm
 
 function createBaseUpdateState(
   channel: DesktopUpdateChannel,
-  enabled: boolean,
+  disabledReason: Option.Option<string>,
   environment: DesktopEnvironment.DesktopEnvironment["Service"],
 ): DesktopUpdateState {
+  const enabled = Option.isNone(disabledReason);
   return {
     ...createInitialDesktopUpdateState(environment.appVersion, environment.runtimeInfo, channel),
     enabled,
     status: enabled ? "idle" : "disabled",
+    message: Option.getOrNull(disabledReason),
   };
 }
 
@@ -468,8 +470,6 @@ export const make = Effect.gen(function* () {
     });
   });
 
-  const shouldEnableAutoUpdates = resolveDisabledReason.pipe(Effect.map(Option.isNone));
-
   const checkForUpdates = Effect.fn("desktop.updates.checkForUpdates")(function* (
     reason: string,
     actionReservation: "acquire" | "held" = "acquire",
@@ -631,10 +631,10 @@ export const make = Effect.gen(function* () {
     ),
   );
 
-  const baseUpdateState = (channel: DesktopUpdateChannel, enabled: boolean) =>
+  const baseUpdateState = (channel: DesktopUpdateChannel, disabledReason: Option.Option<string>) =>
     Ref.get(notAppliedVersionRef).pipe(
       Effect.map((notAppliedVersion) => ({
-        ...createBaseUpdateState(channel, enabled, environment),
+        ...createBaseUpdateState(channel, disabledReason, environment),
         ...Option.match(notAppliedVersion, {
           onNone: () => ({}),
           onSome: (version) => ({ notAppliedVersion: version }),
@@ -1056,9 +1056,9 @@ export const make = Effect.gen(function* () {
       }
 
       const settings = yield* desktopSettings.get;
-      const enabled = yield* shouldEnableAutoUpdates;
-      yield* setState(yield* baseUpdateState(settings.updateChannel, enabled));
-      if (!enabled) {
+      const disabledReason = yield* resolveDisabledReason;
+      yield* setState(yield* baseUpdateState(settings.updateChannel, disabledReason));
+      if (Option.isSome(disabledReason)) {
         return;
       }
       yield* Ref.set(updaterConfiguredRef, true);
@@ -1127,10 +1127,10 @@ export const make = Effect.gen(function* () {
             ),
           );
 
-        const enabled = yield* shouldEnableAutoUpdates;
-        yield* setState(yield* baseUpdateState(nextChannel, enabled));
+        const disabledReason = yield* resolveDisabledReason;
+        yield* setState(yield* baseUpdateState(nextChannel, disabledReason));
 
-        if (!enabled || !(yield* Ref.get(updaterConfiguredRef))) {
+        if (Option.isSome(disabledReason) || !(yield* Ref.get(updaterConfiguredRef))) {
           return yield* Ref.get(updateStateRef);
         }
 
diff --git a/apps/web/src/components/desktopUpdate.logic.test.ts b/apps/web/src/components/desktopUpdate.logic.test.ts
index 3a42348381de..6d9ce611c909 100644
--- a/apps/web/src/components/desktopUpdate.logic.test.ts
+++ b/apps/web/src/components/desktopUpdate.logic.test.ts
@@ -6,6 +6,8 @@ import {
   getArm64IntelBuildWarningDescription,
   getDesktopUpdateActionError,
   getDesktopUpdateButtonTooltip,
+  getDesktopUpdateDisabledReason,
+  getDesktopUpdateIdleTooltip,
   getDesktopUpdateInstallConfirmationMessage,
   getDesktopUpdateReleaseHistoryUrl,
   getDesktopUpdateReleaseUrl,
@@ -391,3 +393,34 @@ describe("getDesktopUpdateButtonTooltip", () => {
     );
   });
 });
+
+describe("disabled update reason", () => {
+  const disabledState: DesktopUpdateState = {
+    ...baseState,
+    enabled: false,
+    status: "disabled",
+    message: "Automatic updates are only available in packaged production builds.",
+  };
+
+  it("explains why checking is unavailable", () => {
+    expect(getDesktopUpdateDisabledReason(disabledState)).toBe(
+      "Automatic updates are only available in packaged production builds.",
+    );
+    expect(getDesktopUpdateIdleTooltip(disabledState)).toEqual({
+      title: "Updates unavailable",
+      detail: "Automatic updates are only available in packaged production builds.",
+    });
+    expect(getDesktopUpdateDisabledReason({ ...disabledState, message: null })).toBe(
+      "Automatic updates are not available in this build.",
+    );
+  });
+
+  it("keeps the check prompt when updates are available", () => {
+    expect(getDesktopUpdateDisabledReason(baseState)).toBeNull();
+    expect(getDesktopUpdateDisabledReason(null)).toBeNull();
+    expect(getDesktopUpdateIdleTooltip(baseState)).toEqual({
+      title: "Check for updates",
+      detail: null,
+    });
+  });
+});
diff --git a/apps/web/src/components/desktopUpdate.logic.ts b/apps/web/src/components/desktopUpdate.logic.ts
index bbef4bf5a4e3..f6d5bc90d60b 100644
--- a/apps/web/src/components/desktopUpdate.logic.ts
+++ b/apps/web/src/components/desktopUpdate.logic.ts
@@ -148,3 +148,19 @@ export function canCheckForUpdate(state: DesktopUpdateState | null): boolean {
     state.status !== "checking" && state.status !== "downloading" && state.status !== "disabled"
   );
 }
+
+export function getDesktopUpdateDisabledReason(
+  state: Pick<DesktopUpdateState, "enabled" | "status" | "message"> | null,
+): string | null {
+  if (!state || (state.enabled && state.status !== "disabled")) return null;
+  return state.message?.trim() || "Automatic updates are not available in this build.";
+}
+
+export function getDesktopUpdateIdleTooltip(
+  state: Pick<DesktopUpdateState, "enabled" | "status" | "message"> | null,
+) {
+  const disabledReason = getDesktopUpdateDisabledReason(state);
+  return disabledReason
+    ? { title: "Updates unavailable", detail: disabledReason }
+    : { title: "Check for updates", detail: null };
+}
diff --git a/apps/web/src/components/settings/SettingsPanels.tsx b/apps/web/src/components/settings/SettingsPanels.tsx
index 949ad3ea1338..5c4cdcaffd73 100644
--- a/apps/web/src/components/settings/SettingsPanels.tsx
+++ b/apps/web/src/components/settings/SettingsPanels.tsx
@@ -60,6 +60,7 @@ import { MobileAppSettingsRow } from "./MobileAppSettingsRow";
 import {
   canCheckForUpdate,
   getDesktopUpdateButtonTooltip,
+  getDesktopUpdateDisabledReason,
   getDesktopUpdateInstallConfirmationMessage,
   isDesktopUpdateButtonDisabled,
   resolveDesktopUpdateButtonAction,
@@ -419,7 +420,7 @@ function AboutVersionSection() {
   const description =
     action === "download" || action === "install"
       ? "Update available."
-      : "Current version of the application.";
+      : (getDesktopUpdateDisabledReason(updateState) ?? "Current version of the application.");
 
   return (
     <>
diff --git a/apps/web/src/components/sidebar/SidebarUpdatePill.tsx b/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
index cfe0ba456829..b7b329de37c9 100644
--- a/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
+++ b/apps/web/src/components/sidebar/SidebarUpdatePill.tsx
@@ -15,6 +15,7 @@ import {
   getDesktopUpdateActionError,
   getDesktopUpdateButtonTooltip,
   getDesktopUpdateDownloadedVersion,
+  getDesktopUpdateIdleTooltip,
   getDesktopUpdateInstallConfirmationMessage,
   isDesktopUpdateButtonDisabled,
   resolveDesktopUpdateButtonAction,
@@ -236,6 +237,8 @@ function SidebarUpdateControl() {
     isDownloading,
     showCheckIcon,
   });
+  const idleTooltip =
+    !showUpdateDetails && !showCheckIcon ? getDesktopUpdateIdleTooltip(state) : null;
   const tooltip = runsEverything
     ? everything.summary
     : showUpdateDetails
@@ -244,7 +247,7 @@ function SidebarUpdateControl() {
         : "Update available"
       : showCheckIcon
         ? "Checking for updates…"
-        : "Check for updates";
+        : (idleTooltip?.title ?? "Check for updates");
   const disabled = showCheckIcon
     ? true
     : runsEverything
@@ -441,7 +444,7 @@ function SidebarUpdateControl() {
   const updateButton = (
     <button
       type="button"
-      aria-label={tooltip}
+      aria-label={idleTooltip?.detail ? `${tooltip}: ${idleTooltip.detail}` : tooltip}
       aria-disabled={isInteractionDisabled || undefined}
       className={cn(
         "inline-flex size-8 items-center justify-center rounded-full outline-hidden ring-ring transition-colors focus-visible:ring-2 focus-visible:ring-inset",
@@ -520,7 +523,14 @@ function SidebarUpdateControl() {
               side="top"
               variant={showUpdateDetails ? "glass" : "default"}
             >
-              <span className="whitespace-pre-line">{tooltip}</span>
+              {idleTooltip?.detail ? (
+                <div className="text-left">
+                  <div className="font-medium">{idleTooltip.title}</div>
+                  <div className="text-muted-foreground">{idleTooltip.detail}</div>
+                </div>
+              ) : (
+                <span className="whitespace-pre-line">{tooltip}</span>
+              )}
             </TooltipPopup>
           ) : null}
         </Tooltip>