diff --git a/apps/web/src/query-client.ts b/apps/web/src/query-client.ts
index e7bc333b9..5b0fbb2f6 100644
--- a/apps/web/src/query-client.ts
+++ b/apps/web/src/query-client.ts
@@ -160,6 +160,24 @@ export const tenantKeys = {
     ] as const,
 };
 
+/**
+ * Every surface that runs a routine (the routine panel's Run now button,
+ * the shell context menu's Run now item) must refresh the same two reads —
+ * the routines list and its run history — or one of them goes stale while
+ * the other doesn't.
+ */
+export function invalidateRoutineQueries(
+  queryClient: QueryClient,
+  tenantId: string,
+): void {
+  void queryClient.invalidateQueries({
+    queryKey: tenantKeys.routines(tenantId),
+  });
+  void queryClient.invalidateQueries({
+    queryKey: tenantKeys.routineRunHistories(tenantId),
+  });
+}
+
 /**
  * Map a hub GET path onto a stable query key. Unknown paths fall back to a
  * path-keyed entry so callers cannot accidentally share cache entries.
diff --git a/apps/web/src/shell/context-menu/items.test.tsx b/apps/web/src/shell/context-menu/items.test.tsx
index df1ca0cb2..7f1997d6e 100644
--- a/apps/web/src/shell/context-menu/items.test.tsx
+++ b/apps/web/src/shell/context-menu/items.test.tsx
@@ -39,6 +39,7 @@ function actions(
     openProfile: mock(() => undefined),
     cycleTheme: mock(() => undefined),
     signOut: mock(() => undefined),
+    onRoutineRan: mock((_tenantId: string) => undefined),
     ...overrides,
   };
 }
@@ -183,6 +184,54 @@ describe("shellContextMenuFor: routine", () => {
     findItem(menu.entries, "open").onSelect();
     expect(navigate).toHaveBeenCalledWith("/routines/rt-1");
   });
+
+  test("run-now invalidates routine queries via onRoutineRan once the run starts", async () => {
+    const realFetch = globalThis.fetch;
+    globalThis.fetch = mock(() =>
+      Promise.resolve(
+        new Response(JSON.stringify({ runId: "run-1" }), {
+          status: 200,
+          headers: { "content-type": "application/json" },
+        }),
+      ),
+    ) as unknown as typeof fetch;
+    const onRoutineRan = mock((_tenantId: string) => undefined);
+    try {
+      const menu = shellContextMenuFor(target, actions({ onRoutineRan }));
+      findItem(menu.entries, "run-now").onSelect();
+      for (let i = 0; i < 10 && onRoutineRan.mock.calls.length === 0; i++) {
+        await Promise.resolve();
+      }
+      expect(onRoutineRan).toHaveBeenCalledWith("tenant-1");
+      expect(toastMock).toHaveBeenCalledWith("Nightly Digest started");
+    } finally {
+      globalThis.fetch = realFetch;
+    }
+  });
+
+  test("run-now does not invalidate routine queries when the run fails to start", async () => {
+    const realFetch = globalThis.fetch;
+    globalThis.fetch = mock(() =>
+      Promise.resolve(
+        new Response(JSON.stringify({ error: { message: "boom" } }), {
+          status: 500,
+          headers: { "content-type": "application/json" },
+        }),
+      ),
+    ) as unknown as typeof fetch;
+    const onRoutineRan = mock((_tenantId: string) => undefined);
+    try {
+      const menu = shellContextMenuFor(target, actions({ onRoutineRan }));
+      findItem(menu.entries, "run-now").onSelect();
+      for (let i = 0; i < 10 && toastMock.mock.calls.length === 0; i++) {
+        await Promise.resolve();
+      }
+      expect(toastMock).toHaveBeenCalledWith("Couldn't start the routine");
+      expect(onRoutineRan).not.toHaveBeenCalled();
+    } finally {
+      globalThis.fetch = realFetch;
+    }
+  });
 });
 
 describe("shellContextMenuFor: insights-run", () => {
diff --git a/apps/web/src/shell/context-menu/items.tsx b/apps/web/src/shell/context-menu/items.tsx
index 8d4a6ac3d..52f6d1d20 100644
--- a/apps/web/src/shell/context-menu/items.tsx
+++ b/apps/web/src/shell/context-menu/items.tsx
@@ -45,6 +45,10 @@ export type ShellContextMenuActions = {
   readonly openProfile: (subject: ProfileSubject) => void;
   readonly cycleTheme: () => void;
   readonly signOut: () => void;
+  /** Called with the tenant id after a routine's Run now succeeds, so the
+   * caller can refresh the routines list and run history that a stale
+   * right-click menu has no other way to know changed. */
+  readonly onRoutineRan: (tenantId: string) => void;
 };
 
 async function copyLink(path: string, label: string): Promise<void> {
@@ -152,7 +156,10 @@ function routineMenu(
         icon: <PlayCircle />,
         onSelect: () => {
           void runRoutineNow(tenantId, target.id).then(
-            () => toast(`${target.name} started`),
+            () => {
+              toast(`${target.name} started`);
+              actions.onRoutineRan(tenantId);
+            },
             () => toast("Couldn't start the routine"),
           );
         },
diff --git a/apps/web/src/shell/context-menu/shell-context-menu.tsx b/apps/web/src/shell/context-menu/shell-context-menu.tsx
index 7f3222743..5465cf1f7 100644
--- a/apps/web/src/shell/context-menu/shell-context-menu.tsx
+++ b/apps/web/src/shell/context-menu/shell-context-menu.tsx
@@ -9,10 +9,12 @@ import {
   useContextMenuState,
   useDocumentContextMenuTrigger,
 } from "@corbits/context-menu";
+import { useQueryClient } from "@tanstack/react-query";
 import { useCallback } from "react";
 
 import { useBench } from "../../bench-context";
 import { useNavigate } from "../../navigation";
+import { invalidateRoutineQueries } from "../../query-client";
 import { useOpenProfileInCanvas } from "../canvas-availability";
 import { shellContextMenuFor } from "./items";
 import type { ShellContextMenuActions } from "./items";
@@ -30,6 +32,7 @@ export function ShellContextMenu({
   const navigate = useNavigate();
   const openProfile = useOpenProfileInCanvas();
   const { cycleMode } = useTheme();
+  const queryClient = useQueryClient();
   const { open, x, y, menu, triggerElement, show, hide } =
     useContextMenuState();
 
@@ -39,6 +42,7 @@ export function ShellContextMenu({
     openProfile,
     cycleTheme: cycleMode,
     signOut: onSignOut,
+    onRoutineRan: (tenantId) => invalidateRoutineQueries(queryClient, tenantId),
   };
 
   const resolve = useCallback(
@@ -52,7 +56,14 @@ export function ShellContextMenu({
     },
     // `actions` is a fresh object every render; the values it closes over
     // are what actually determine the menu, so those are the real deps.
-    [selectedTenantId, navigate, openProfile, cycleMode, onSignOut],
+    [
+      selectedTenantId,
+      navigate,
+      openProfile,
+      cycleMode,
+      onSignOut,
+      queryClient,
+    ],
   );
 
   useDocumentContextMenuTrigger({ resolve, onOpen: show });
diff --git a/apps/web/src/shell/routine-panel.tsx b/apps/web/src/shell/routine-panel.tsx
index 34b010527..771d4c077 100644
--- a/apps/web/src/shell/routine-panel.tsx
+++ b/apps/web/src/shell/routine-panel.tsx
@@ -76,7 +76,7 @@ import {
   slackTriggerOffered,
 } from "../deployment-capabilities-api";
 import { useGranolaPluginConnected } from "../granola-plugin-availability";
-import { tenantKeys } from "../query-client";
+import { invalidateRoutineQueries } from "../query-client";
 import { useCanvasColumnRoutine, useCloseCanvas } from "./canvas-availability";
 import type { RoutinePanelSubject } from "./canvas-availability";
 import { CanvasPaneHeader } from "./canvas-column";
@@ -202,12 +202,7 @@ function RoutineEditorPanel({
 
   const invalidateRoutines = () => {
     if (tenantId === null) return;
-    void queryClient.invalidateQueries({
-      queryKey: tenantKeys.routines(tenantId),
-    });
-    void queryClient.invalidateQueries({
-      queryKey: tenantKeys.routineRunHistories(tenantId),
-    });
+    invalidateRoutineQueries(queryClient, tenantId);
   };
 
   const [routineId, setRoutineId] = useState<string | null>(