diff --git a/apps/web/src/pages/routine-detail-page.tsx b/apps/web/src/pages/routine-detail-page.tsx
index 161f6e5b0..b81e1b0b0 100644
--- a/apps/web/src/pages/routine-detail-page.tsx
+++ b/apps/web/src/pages/routine-detail-page.tsx
@@ -365,14 +365,26 @@ export function RoutineDetailPage({
         subtitle={row.tenantName}
         actions={
           <>
-            <RunNowButton variant="outline" size="sm" onRun={onRunNow} />
-            <Button
-              type="button"
-              size="sm"
-              onClick={() => onToggleEnabled(!row.routine.enabled)}
-            >
-              {row.routine.enabled ? "Pause" : "Resume"}
-            </Button>
+            {!row.routine.enabled || health.state === "paused" ? (
+              <Button
+                type="button"
+                size="sm"
+                onClick={() => onToggleEnabled(true)}
+              >
+                Resume
+              </Button>
+            ) : (
+              <>
+                <RunNowButton variant="outline" size="sm" onRun={onRunNow} />
+                <Button
+                  type="button"
+                  size="sm"
+                  onClick={() => onToggleEnabled(false)}
+                >
+                  Pause
+                </Button>
+              </>
+            )}
             <Button type="button" variant="outline" size="sm" onClick={onEdit}>
               Edit
             </Button>
diff --git a/apps/web/src/pages/routines-page.tsx b/apps/web/src/pages/routines-page.tsx
index 8fd0d2f60..c36de50f7 100644
--- a/apps/web/src/pages/routines-page.tsx
+++ b/apps/web/src/pages/routines-page.tsx
@@ -351,7 +351,7 @@ export function GlobalRoutinesList({
               <TableCell>
                 <Switch
                   checked={row.routine.enabled}
-                  label={`${row.routine.enabled ? "Pause" : "Resume"} ${row.routine.name}`}
+                  label={`${row.routine.enabled ? "On" : "Off"} ${row.routine.name}`}
                   onCheckedChange={(enabled) => onToggleEnabled(row, enabled)}
                 />
               </TableCell>
diff --git a/apps/web/test/routine-detail-page.test.tsx b/apps/web/test/routine-detail-page.test.tsx
index da56c0100..cf0307db5 100644
--- a/apps/web/test/routine-detail-page.test.tsx
+++ b/apps/web/test/routine-detail-page.test.tsx
@@ -173,6 +173,32 @@ describe("RoutineDetailPage", () => {
     expect(actions).toContain("Run now");
     expect(actions).toContain("Pause");
   });
+
+  function topBarActions(markup: string): string {
+    const start = markup.indexOf('data-testid="stage-top-bar-actions"');
+    const end = markup.indexOf("</header>", start);
+    return markup.slice(start, end === -1 ? undefined : end);
+  }
+
+  test("hides Run now when the routine is off, and offers Resume only", () => {
+    const actions = topBarActions(
+      renderPage({ routine: { ...routine, enabled: false } }),
+    );
+    expect(actions).toContain("Resume");
+    expect(actions).not.toContain("Run now");
+    expect(actions).not.toContain("Pause");
+  });
+
+  test("hides Run now when the routine is dead-lettered, and offers Resume only", () => {
+    const actions = topBarActions(
+      renderPage({
+        routine: { ...routine, deadLetteredAt: "2026-01-02T00:00:00.000Z" },
+      }),
+    );
+    expect(actions).toContain("Resume");
+    expect(actions).not.toContain("Run now");
+    expect(actions).not.toContain("Pause");
+  });
 });
 
 describe("RoutineDetailPage lifecycle actions", () => {
@@ -237,6 +263,21 @@ describe("RoutineDetailPage lifecycle actions", () => {
     }
   });
 
+  test("Resume on a dead-lettered routine asks for it to be enabled again", () => {
+    const calls: boolean[] = [];
+    const { container, root } = mount(
+      { onToggleEnabled: (enabled: boolean) => calls.push(enabled) },
+      { routine: { ...routine, deadLetteredAt: "2026-01-02T00:00:00.000Z" } },
+    );
+    try {
+      clickButton(container, "Resume");
+      expect(calls).toEqual([true]);
+    } finally {
+      act(() => root.unmount());
+      container.remove();
+    }
+  });
+
   test("Run now triggers the run-now mutation", () => {
     let runs = 0;
     const { container, root } = mount({
@@ -254,6 +295,37 @@ describe("RoutineDetailPage lifecycle actions", () => {
     }
   });
 
+  test("Run now reads as starting while the request is in flight", async () => {
+    let resolveRun: () => void = () => undefined;
+    const pending = new Promise<void>((resolve) => {
+      resolveRun = resolve;
+    });
+    const { container, root } = mount({
+      onRunNow: () => pending,
+    });
+    try {
+      clickButton(container, "Run now");
+      const button = [...container.querySelectorAll("button")].find(
+        (candidate) => candidate.textContent?.includes("Starting") === true,
+      );
+      expect(button).not.toBeUndefined();
+      expect(button?.disabled).toBe(true);
+
+      await act(async () => {
+        resolveRun();
+        await pending;
+      });
+      expect(
+        [...container.querySelectorAll("button")].some(
+          (candidate) => candidate.textContent?.includes("Starting") === true,
+        ),
+      ).toBe(false);
+    } finally {
+      act(() => root.unmount());
+      container.remove();
+    }
+  });
+
   test("Edit opens the routine's editor", () => {
     let edits = 0;
     const { container, root } = mount({
diff --git a/apps/web/test/routines-page.test.tsx b/apps/web/test/routines-page.test.tsx
index 62e306bff..44b8f675e 100644
--- a/apps/web/test/routines-page.test.tsx
+++ b/apps/web/test/routines-page.test.tsx
@@ -262,6 +262,20 @@ describe("GlobalRoutinesList", () => {
     expect(markup).toContain("—");
   });
 
+  test("the On switch is named On, not Pause, while the routine is enabled", () => {
+    const markup = renderList([row()]);
+    expect(markup).toContain('aria-label="On Morning brief"');
+    expect(markup).not.toContain('aria-label="Pause Morning brief"');
+  });
+
+  test("the On switch is named Off when the routine is disabled", () => {
+    const markup = renderList([
+      row({ routine: { ...routine, enabled: false } }),
+    ]);
+    expect(markup).toContain('aria-label="Off Morning brief"');
+    expect(markup).not.toContain('aria-label="Resume Morning brief"');
+  });
+
   test("Run now calls onRunNow with the row", async () => {
     const calls: GlobalRoutineRow[] = [];
     const container = document.createElement("div");
@@ -371,6 +385,16 @@ describe("GlobalRoutinesList", () => {
     }
   });
 
+  test("a dead-lettered routine's action reads Resume, not Run now", () => {
+    const markup = renderList([
+      row({
+        routine: { ...routine, deadLetteredAt: "2026-01-02T00:00:00.000Z" },
+      }),
+    ]);
+    expect(markup).toContain("Resume");
+    expect(markup).not.toContain("Run now");
+  });
+
   test("Edit calls onEditRoutine with the row", () => {
     const calls: GlobalRoutineRow[] = [];
     const container = document.createElement("div");