diff --git a/apps/web/src/components/settings/automations/AutomationsSettings.render.client.test.tsx b/apps/web/src/components/settings/automations/AutomationsSettings.render.client.test.tsx
index b6a9b053e..58079bda3 100644
--- a/apps/web/src/components/settings/automations/AutomationsSettings.render.client.test.tsx
+++ b/apps/web/src/components/settings/automations/AutomationsSettings.render.client.test.tsx
@@ -6,11 +6,13 @@ import {
   screen,
   waitFor,
 } from '@testing-library/react';
+import { toast } from 'sonner';
 const managerInstructionsPlaceholder =
   /Optional guidance for which ideas to prioritize or avoid/;
 
 const state = vi.hoisted(() => ({
   customAutomationsPending: false,
+  customAutomationRunPendingId: null as string | null,
   customAutomations: [] as Array<{
     id: string;
     name: string;
@@ -252,9 +254,13 @@ const mutations = vi.hoisted(() => ({
   } | null,
   latestTriggerOptions: null as {
     onSuccess?: (
-      result: NonNullable<typeof state.nextUpdateSettingsResult>,
+      result: { outcome: 'launched'; taskId: string },
+      variables: { automationKey: string },
     ) => void;
   } | null,
+  latestCustomTriggerOptions: null as {
+    onSuccess?: (result: { outcome: 'launched'; taskId: string }) => void;
+  } | null,
 }));
 
 vi.mock('next/link', () => ({
@@ -276,6 +282,8 @@ vi.mock('sonner', () => ({
   toast: {
     success: vi.fn(),
     error: vi.fn(),
+    info: vi.fn(),
+    message: vi.fn(),
   },
 }));
 
@@ -364,9 +372,13 @@ vi.mock('@tanstack/react-query', () => ({
     ) => void;
     onError?: (...args: unknown[]) => void;
     mutationKind?: 'triggerCustomAutomation';
+    mutationKey?: unknown[];
   }) => {
     return {
-      isPending: false,
+      isPending:
+        _options?.mutationKind === 'triggerCustomAutomation' &&
+        (typeof _options.mutationKey?.[1] !== 'string' ||
+          _options.mutationKey[1] === state.customAutomationRunPendingId),
       mutate: vi.fn((variables: unknown) => {
         if (_options?.mutationKind === 'triggerCustomAutomation') {
           mutations.triggerCustomAutomation(variables);
@@ -421,10 +433,15 @@ vi.mock('@/trpc/client', () => ({
         mutationOptions: (options?: Record<string, unknown>) => options ?? {},
       },
       triggerCustomAutomation: {
-        mutationOptions: (options?: Record<string, unknown>) => ({
-          ...options,
-          mutationKind: 'triggerCustomAutomation',
-        }),
+        mutationOptions: (options?: Record<string, unknown>) => {
+          mutations.latestCustomTriggerOptions =
+            (options as typeof mutations.latestCustomTriggerOptions) ?? null;
+
+          return {
+            ...options,
+            mutationKind: 'triggerCustomAutomation',
+          };
+        },
       },
       resolveCustomAutomationSchedule: {
         mutationOptions: (options?: Record<string, unknown>) => options ?? {},
@@ -504,8 +521,10 @@ describe('AutomationsSettings', () => {
   beforeEach(() => {
     vi.clearAllMocks();
     state.nextUpdateSettingsResult = null;
+    state.customAutomationRunPendingId = null;
     mutations.latestSettingsOptions = null;
     mutations.latestTriggerOptions = null;
+    mutations.latestCustomTriggerOptions = null;
     state.settingsQuery.data.capabilities.slackConnected = true;
     state.settingsQuery.data.capabilities.discordConnected = false;
     state.settingsQuery.data.capabilities.telegramConnected = false;
@@ -895,6 +914,24 @@ describe('AutomationsSettings', () => {
     ).toBeInTheDocument();
   });
 
+  it('names built-in automations in run-now task toasts', () => {
+    render(<AutomationsSettings />);
+
+    act(() => {
+      mutations.latestTriggerOptions?.onSuccess?.(
+        { outcome: 'launched', taskId: 'task-built-in-1' },
+        { automationKey: 'suggester' },
+      );
+    });
+
+    expect(toast.success).toHaveBeenCalledWith(
+      'Running Suggest Ideas now',
+      expect.objectContaining({
+        action: expect.objectContaining({ label: 'View task' }),
+      }),
+    );
+  });
+
   it('renders custom automations as a compact control list and honors their permalinks', async () => {
     state.environments = [{ id: 'env-1', name: 'Production' }];
     state.customAutomations = [
@@ -937,6 +974,35 @@ describe('AutomationsSettings', () => {
     expect(mutations.triggerCustomAutomation).toHaveBeenCalledWith({
       id: 'automation-1',
     });
+    act(() => {
+      mutations.latestCustomTriggerOptions?.onSuccess?.({
+        outcome: 'launched',
+        taskId: 'task-custom-1',
+      });
+    });
+    expect(toast.success).toHaveBeenCalledWith(
+      'Running Weekly flaky-test scan now',
+      expect.objectContaining({
+        action: expect.objectContaining({ label: 'View task' }),
+      }),
+    );
+
+    state.customAutomations.push({
+      ...state.customAutomations[0]!,
+      id: 'automation-2',
+      name: 'Daily dependency scan',
+    });
+    state.customAutomationRunPendingId = 'automation-1';
+    rerender(<AutomationsSettings />);
+    expect(
+      screen.getByRole('button', { name: 'Run Weekly flaky-test scan now' }),
+    ).toBeDisabled();
+    expect(
+      screen.getByRole('button', { name: 'Run Daily dependency scan now' }),
+    ).toBeEnabled();
+    expect(screen.getByRole('button', { name: 'New' })).toBeEnabled();
+
+    state.customAutomationRunPendingId = null;
     state.customAutomations[0]!.enabled = false;
     rerender(<AutomationsSettings />);
     expect(
diff --git a/apps/web/src/components/settings/automations/AutomationsSettings.tsx b/apps/web/src/components/settings/automations/AutomationsSettings.tsx
index e529c4e6a..27935608e 100644
--- a/apps/web/src/components/settings/automations/AutomationsSettings.tsx
+++ b/apps/web/src/components/settings/automations/AutomationsSettings.tsx
@@ -1800,9 +1800,9 @@ export function AutomationsSettings() {
 
         switch (data.outcome) {
           case 'launched':
-            toast.success(`${automationLabel} started a task.`, {
+            toast.success(`Running ${automationLabel} now`, {
               action: {
-                label: 'Open task',
+                label: 'View task',
                 onClick: () => window.open(`/task/${data.taskId}`, '_blank'),
               },
             });
diff --git a/apps/web/src/components/settings/automations/CustomAutomationsSection.tsx b/apps/web/src/components/settings/automations/CustomAutomationsSection.tsx
index 1d24f7950..8e218f234 100644
--- a/apps/web/src/components/settings/automations/CustomAutomationsSection.tsx
+++ b/apps/web/src/components/settings/automations/CustomAutomationsSection.tsx
@@ -119,6 +119,62 @@ function cadenceLabel(row: CustomAutomationListItem): string {
     : 'Custom schedule';
 }
 
+function CustomAutomationRunButton({
+  automation,
+  disabled,
+}: {
+  automation: CustomAutomationListItem;
+  disabled: boolean;
+}) {
+  const trpc = useTRPC();
+  const triggerMutation = useMutation({
+    ...trpc.automations.triggerCustomAutomation.mutationOptions({
+      onSuccess: (result) => {
+        switch (result.outcome) {
+          case 'launched':
+            toast.success(`Running ${automation.name} now`, {
+              action: {
+                label: 'View task',
+                onClick: () => window.open(`/task/${result.taskId}`, '_blank'),
+              },
+            });
+            break;
+          case 'completed':
+            toast.success(`${automation.name} ran successfully.`);
+            break;
+          case 'skipped':
+            toast.info(
+              `${automation.name} had nothing to do: ${result.reason}`,
+            );
+            break;
+          case 'failed':
+            toast.error(`${automation.name} failed: ${result.error}`);
+            break;
+        }
+      },
+      onError: (error) => {
+        toast.error(error.message || `Failed to run ${automation.name}`);
+      },
+    }),
+    mutationKey: ['customAutomationRun', automation.id],
+  });
+
+  return (
+    <BasicTooltip content="Run now">
+      <Button
+        type="button"
+        size="icon"
+        variant="ghost"
+        disabled={disabled || triggerMutation.isPending || !automation.enabled}
+        aria-label={`Run ${automation.name} now`}
+        onClick={() => triggerMutation.mutate({ id: automation.id })}
+      >
+        <Play />
+      </Button>
+    </BasicTooltip>
+  );
+}
+
 function targetFromRow(row: CustomAutomationListItem): {
   provider: CustomAutomationFormState['targetProvider'];
   channelId: string;
@@ -350,35 +406,6 @@ export function CustomAutomationsSection() {
     }),
   );
 
-  const triggerMutation = useMutation(
-    trpc.automations.triggerCustomAutomation.mutationOptions({
-      onSuccess: (result) => {
-        switch (result.outcome) {
-          case 'launched':
-            toast.success('Custom automation started a task.', {
-              action: {
-                label: 'Open task',
-                onClick: () => window.open(`/task/${result.taskId}`, '_blank'),
-              },
-            });
-            break;
-          case 'completed':
-            toast.success('Custom automation ran successfully.');
-            break;
-          case 'skipped':
-            toast.info(`Custom automation had nothing to do: ${result.reason}`);
-            break;
-          case 'failed':
-            toast.error(`Custom automation failed: ${result.error}`);
-            break;
-        }
-      },
-      onError: (error) => {
-        toast.error(error.message || 'Failed to run custom automation');
-      },
-    }),
-  );
-
   const resolveScheduleMutation = useMutation(
     trpc.automations.resolveCustomAutomationSchedule.mutationOptions({
       onSuccess: (result, variables) => {
@@ -431,8 +458,7 @@ export function CustomAutomationsSection() {
     createMutation.isPending ||
     updateMutation.isPending ||
     deleteMutation.isPending ||
-    toggleMutation.isPending ||
-    triggerMutation.isPending;
+    toggleMutation.isPending;
 
   const closeEditor = () => {
     setIsCreating(false);
@@ -1062,18 +1088,10 @@ export function CustomAutomationsSection() {
                       </p>
                     </div>
                     <div className="col-start-2 row-start-2 flex shrink-0 items-center gap-1 sm:col-start-3 sm:row-start-1">
-                      <BasicTooltip content="Run now">
-                        <Button
-                          type="button"
-                          size="icon"
-                          variant="ghost"
-                          disabled={busy || !row.enabled}
-                          aria-label={`Run ${row.name} now`}
-                          onClick={() => triggerMutation.mutate({ id: row.id })}
-                        >
-                          <Play />
-                        </Button>
-                      </BasicTooltip>
+                      <CustomAutomationRunButton
+                        automation={row}
+                        disabled={busy}
+                      />
                       <BasicTooltip content="Configure">
                         <Button
                           type="button"