diff --git a/packages/app/e2e/file-editing.spec.ts b/packages/app/e2e/file-editing.spec.ts
index 2a2c7dc11..e6d1cab4b 100644
--- a/packages/app/e2e/file-editing.spec.ts
+++ b/packages/app/e2e/file-editing.spec.ts
@@ -90,6 +90,27 @@ test.describe("CodeMirror workspace file editing", () => {
     await expect(selection).toHaveCSS("background-color", "rgba(255, 255, 255, 0.2)");
   });
 
+  test("applies the interface font to portaled tooltips", async ({ page, withWorkspace }) => {
+    await page.addInitScript(() => {
+      localStorage.setItem("@paseo:app-settings", JSON.stringify({ uiFontFamily: "monospace" }));
+    });
+    const workspace = await withWorkspace({ prefix: "file-tooltip-font-" });
+    const relativePath = "tooltip-font.txt";
+    await writeFile(path.join(workspace.repoPath, relativePath), "tooltip font\n", "utf8");
+    await workspace.navigateTo();
+    await openFileExplorer(page);
+    await openFileFromExplorer(page, relativePath);
+    await expectFileTabOpen(page, relativePath);
+
+    await page.getByTestId(`workspace-tab-file_${relativePath}`).first().hover();
+
+    await expect(
+      page
+        .getByTestId(`workspace-tab-tooltip-file_${relativePath}`)
+        .getByText(relativePath, { exact: true }),
+    ).toHaveCSS("font-family", "monospace");
+  });
+
   test("autosaves, saves immediately, resolves conflicts, and restores live updates after reconnect", async ({
     page,
     withWorkspace,
diff --git a/packages/app/src/screens/settings/appearance/apply-root-font.web.ts b/packages/app/src/screens/settings/appearance/apply-root-font.web.ts
index 3fdfe615c..16a263014 100644
--- a/packages/app/src/screens/settings/appearance/apply-root-font.web.ts
+++ b/packages/app/src/screens/settings/appearance/apply-root-font.web.ts
@@ -8,7 +8,8 @@
 // on stylesheet order. Code/diff/terminal surfaces carry `data-pmono` (and have their
 // subtree excluded via `:not([data-pmono] *)`) so they keep their monospace font.
 const STYLE_ID = "paseo-ui-font";
-const RULE = "#root *:not([data-pmono]):not([data-pmono] *){font-family:var(--paseo-ui-font);}";
+const RULE =
+  ":is(#root, #overlay-root) *:not([data-pmono]):not([data-pmono] *){font-family:var(--paseo-ui-font);}";
 
 export function applyRootUiFont(uiFontStack: string): void {
   if (typeof document === "undefined") return;
diff --git a/packages/app/src/styles/code-surface.ts b/packages/app/src/styles/code-surface.ts
index bdf20eed4..cd067ce52 100644
--- a/packages/app/src/styles/code-surface.ts
+++ b/packages/app/src/styles/code-surface.ts
@@ -1,7 +1,7 @@
 // Marker for code / diff / monospace surfaces. On web, the app-wide interface-font
 // rule (see screens/settings/appearance/apply-root-font.web.ts) targets
-// `#root *:not([data-pmono]):not([data-pmono] *)`, so tagging a code container with
-// this dataSet excludes it and its subtree — they keep their monospace font. On
-// native it renders nothing and is harmless. Use a shared stable reference so it
-// doesn't trip the react-perf "new object as prop" rule.
+// app and overlay roots while excluding `[data-pmono]` subtrees, so tagging a code
+// container with this dataSet keeps its monospace font. On native it renders nothing
+// and is harmless. Use a shared stable reference so it doesn't trip the react-perf
+// "new object as prop" rule.
 export const CODE_SURFACE_DATASET = { pmono: "" } as const;