diff --git a/packages/app/e2e/browser/context-window-meter.spec.ts b/packages/app/e2e/browser/context-window-meter.spec.ts
index d54bf977fc..6d37157d84 100644
--- a/packages/app/e2e/browser/context-window-meter.spec.ts
+++ b/packages/app/e2e/browser/context-window-meter.spec.ts
@@ -89,7 +89,9 @@ test.describe("context window meter", () => {
     }
   });
 
-  test("shows the host's plan limits in the context tooltip", async ({ page }) => {
+  test("shows host plan limits and lets keyboard users enter the context tooltip", async ({
+    page,
+  }) => {
     test.setTimeout(180_000);
     const usage = await installUsageReportsFixture(page, { lists: [[contextUsageReport()]] });
     const session = await seedMockAgentWorkspace({
@@ -102,22 +104,32 @@ test.describe("context window meter", () => {
       await expectComposerVisible(page);
       const meter = page.getByTestId("context-window-meter");
       await expect(meter).toHaveAccessibleName(/25%/, { timeout: 30_000 });
-      await meter.hover();
       await usage.waitForListRequests(1);
 
+      // The preceding Tab marks this as keyboard focus; tooltips deliberately ignore restored focus.
+      await page.keyboard.press("Tab");
+      await meter.focus();
+
       const tooltip = page.getByTestId("context-window-meter-tooltip");
       await expect(tooltip.getByText("Mock plan", { exact: true })).toBeVisible();
       await expect(tooltip.getByText("42% used", { exact: true })).toBeVisible();
-      const pin = tooltip.getByRole("checkbox", { name: /Pin Mock plan Session/ });
-      await pin.click();
-      await expect(pin).toBeChecked();
-
-      await tooltip.getByRole("button", { name: "Refresh Mock plan" }).click();
+      const refresh = tooltip.getByRole("button", { name: "Refresh Mock plan" });
+      await page.keyboard.press("Tab");
+      await expect(refresh).toBeFocused();
+      await page.keyboard.press("Enter");
       await usage.waitForListRequests(2);
       expect(usage.listRequests()[1]).toMatchObject({
         forceRefresh: true,
         reportIds: ["mock:account"],
       });
+
+      const pin = tooltip.getByRole("checkbox", { name: /Pin Mock plan Session/ });
+      await page.keyboard.press("Tab");
+      await expect(pin).toBeFocused();
+      await page.keyboard.press("Space");
+      await expect(pin).toBeChecked();
+      await pin.click();
+      await expect(pin).not.toBeChecked();
     } finally {
       await session.cleanup();
     }
diff --git a/packages/app/src/components/ui/tooltip.tsx b/packages/app/src/components/ui/tooltip.tsx
index 84b780cbda..d2a3332fd1 100644
--- a/packages/app/src/components/ui/tooltip.tsx
+++ b/packages/app/src/components/ui/tooltip.tsx
@@ -47,6 +47,8 @@ interface TooltipContextValue {
   cancelClose: () => void;
   scheduleClose: () => void;
   triggerRef: React.RefObject<View | null>;
+  contentRef: React.RefObject<View | null>;
+  focusContent: () => boolean;
   enabled: boolean;
   openOnPress: boolean;
   delayDuration: number;
@@ -101,6 +103,17 @@ function composeEventHandlers(
   };
 }
 
+function focusFirstContentControl(content: View | null): boolean {
+  if (!isWeb || typeof document === "undefined" || !content) return false;
+  const root = content as unknown as HTMLElement;
+  const control = root.querySelector<HTMLElement>(
+    '[role="button"][tabindex]:not([aria-disabled="true"]), [role="checkbox"][tabindex]:not([aria-disabled="true"]), a[href], input:not([disabled]), select:not([disabled]), textarea:not([disabled])',
+  );
+  if (!control) return false;
+  control.focus();
+  return document.activeElement === control;
+}
+
 function useControllableOpenState({
   open,
   defaultOpen,
@@ -247,6 +260,7 @@ export function Tooltip({
   interactive?: boolean;
 }>): ReactElement {
   const triggerRef = useRef<View>(null);
+  const contentRef = useRef<View>(null);
   const closeTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
   const [isOpen, setIsOpen] = useControllableOpenState({
     open,
@@ -274,6 +288,7 @@ export function Tooltip({
       closeTimerRef.current = null;
     }, 100);
   }, [cancelClose, interactive, setIsOpen]);
+  const focusContent = useCallback(() => focusFirstContentControl(contentRef.current), []);
 
   useEffect(() => cancelClose, [cancelClose]);
 
@@ -284,6 +299,8 @@ export function Tooltip({
       cancelClose,
       scheduleClose,
       triggerRef,
+      contentRef,
+      focusContent,
       enabled,
       openOnPress: opensOnPress,
       delayDuration,
@@ -294,6 +311,7 @@ export function Tooltip({
       setIsOpen,
       cancelClose,
       scheduleClose,
+      focusContent,
       enabled,
       opensOnPress,
       delayDuration,
@@ -311,6 +329,7 @@ export function TooltipTrigger({
   onHoverOut,
   onFocus,
   onBlur,
+  onKeyDown,
   onPress,
   asChild = false,
   triggerRefProp = "ref",
@@ -318,6 +337,7 @@ export function TooltipTrigger({
 }: PressableProps & {
   asChild?: boolean;
   triggerRefProp?: string;
+  onKeyDown?: (event: unknown) => void;
 }): ReactElement {
   const ctx = useTooltipContext("TooltipTrigger");
   const openTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
@@ -388,6 +408,21 @@ export function TooltipTrigger({
     [close, onBlur],
   );
 
+  const handleKeyDown = useCallback(
+    (event: unknown) => {
+      if (isCallable(onKeyDown)) onKeyDown(event);
+      if (!ctx.interactive || !ctx.open) return;
+      const keyboardEvent = event as {
+        key?: unknown;
+        shiftKey?: unknown;
+        preventDefault?: () => void;
+      };
+      if (keyboardEvent.key !== "Tab" || keyboardEvent.shiftKey) return;
+      if (ctx.focusContent()) keyboardEvent.preventDefault?.();
+    },
+    [ctx, onKeyDown],
+  );
+
   const handlePress = useCallback(
     (e: unknown) => {
       if (isCallable(onPress)) onPress(e);
@@ -412,6 +447,7 @@ export function TooltipTrigger({
     onHoverOut: handleHoverOut,
     onFocus: handleFocus,
     onBlur: handleBlur,
+    onKeyDown: handleKeyDown,
     onPress: handlePress,
     ...(isWeb
       ? ({
@@ -442,6 +478,7 @@ export function TooltipTrigger({
       onHoverOut: composeEventHandlers(Reflect.get(rawProps, "onHoverOut"), handleHoverOut),
       onFocus: composeEventHandlers(Reflect.get(rawProps, "onFocus"), handleFocus),
       onBlur: composeEventHandlers(Reflect.get(rawProps, "onBlur"), handleBlur),
+      onKeyDown: composeEventHandlers(Reflect.get(rawProps, "onKeyDown"), handleKeyDown),
       onPress: composeEventHandlers(Reflect.get(rawProps, "onPress"), handlePress),
       onPointerEnter: composeEventHandlers(Reflect.get(rawProps, "onPointerEnter"), handleHoverIn),
       onPointerLeave: composeEventHandlers(Reflect.get(rawProps, "onPointerLeave"), handleHoverOut),
@@ -561,6 +598,7 @@ export function TooltipContent({
       <View pointerEvents={ctx.interactive ? "box-none" : "none"} style={styles.portalOverlay}>
         <FloatingSurface
           pointerEvents={ctx.interactive ? "auto" : "none"}
+          ref={ctx.contentRef}
           entering={FadeIn.duration(80)}
           exiting={FadeOut.duration(80)}
           collapsable={false}
@@ -597,6 +635,7 @@ export function TooltipContent({
           />
           <FloatingSurface
             pointerEvents="auto"
+            ref={ctx.contentRef}
             entering={FadeIn.duration(80)}
             exiting={FadeOut.duration(80)}
             collapsable={false}
@@ -614,6 +653,7 @@ export function TooltipContent({
         <Pressable testID="tooltip-dismiss" style={styles.overlay} onPress={handleDismiss}>
           <FloatingSurface
             pointerEvents="none"
+            ref={ctx.contentRef}
             entering={FadeIn.duration(80)}
             exiting={FadeOut.duration(80)}
             collapsable={false}