diff --git a/apps/web/src/components/ChatMarkdown.browser.test.tsx b/apps/web/src/components/ChatMarkdown.browser.test.tsx
index 66dc5c150a65..ae678a02c834 100644
--- a/apps/web/src/components/ChatMarkdown.browser.test.tsx
+++ b/apps/web/src/components/ChatMarkdown.browser.test.tsx
@@ -3,7 +3,7 @@ import { EnvironmentId, ThreadId } from "@t3tools/contracts";
 import { AsyncResult } from "effect/reactivity";
 import { type ReactElement } from "react";
 import { describe, expect, it, vi } from "vite-plus/test";
-import { page, userEvent } from "vite-plus/test/browser";
+import { commands, page, userEvent } from "vite-plus/test/browser";
 
 import { act, render } from "../../test/render";
 import "../index.css";
@@ -682,6 +682,22 @@ describe("ChatMarkdown alert copy", () => {
 });
 
 describe("ChatMarkdown file chip tooltips", () => {
+  it("stays open while the pointer selects the path, then closes when it leaves", async () => {
+    setup();
+    await using screen = await renderText("[notes](/tmp/project/docs/notes.md)");
+    await userEvent.hover(screen.container.querySelector(".chat-markdown-file-link")!);
+    const path = page.getByText("/tmp/project/docs/notes.md");
+    await expect.element(path).toBeVisible();
+
+    // Forced so the pointer lands on the popup even when it ignores pointer events.
+    await userEvent.tripleClick(path, { force: true });
+    expect(window.getSelection()?.toString().trim()).toBe("/tmp/project/docs/notes.md");
+    await expect.element(path).toBeVisible();
+
+    await commands.resetPointer();
+    await expect.element(path).not.toBeInTheDocument();
+  });
+
   it("wraps a long path so its file name stays inside the tooltip", async () => {
     setup();
     const path =
diff --git a/apps/web/src/components/ComposerPromptEditorTiptap.tsx b/apps/web/src/components/ComposerPromptEditorTiptap.tsx
index 5a036e34611e..d6354080e832 100644
--- a/apps/web/src/components/ComposerPromptEditorTiptap.tsx
+++ b/apps/web/src/components/ComposerPromptEditorTiptap.tsx
@@ -300,7 +300,7 @@ function ComposerMentionNodeView({ node }: NodeViewProps) {
     <NodeViewWrapper as="span" className={CHIP_NODE_SELECTION_CLASS_NAME}>
       <Tooltip>
         <TooltipTrigger render={chip} />
-        <TooltipPopup side="top">
+        <TooltipPopup side="top" className="pointer-events-auto">
           <WorkspaceEntryTooltip
             path={path}
             environmentId={actions.environmentId}
diff --git a/apps/web/src/components/chat/MarkdownFileLink.tsx b/apps/web/src/components/chat/MarkdownFileLink.tsx
index 0fa8eaf4f30f..ac8933395013 100644
--- a/apps/web/src/components/chat/MarkdownFileLink.tsx
+++ b/apps/web/src/components/chat/MarkdownFileLink.tsx
@@ -391,7 +391,7 @@ export const MarkdownFileLink = memo(function MarkdownFileLink({
           )
         }
       />
-      <TooltipPopup side="top" variant="code">
+      <TooltipPopup side="top" variant="code" className="pointer-events-auto">
         <WorkspaceEntryTooltip path={iconPath} label={targetPath} environmentId={environmentId} />
       </TooltipPopup>
     </Tooltip>
diff --git a/apps/web/src/components/chat/UserMessageContextChips.tsx b/apps/web/src/components/chat/UserMessageContextChips.tsx
index 39801a908b95..d6c320d09054 100644
--- a/apps/web/src/components/chat/UserMessageContextChips.tsx
+++ b/apps/web/src/components/chat/UserMessageContextChips.tsx
@@ -92,7 +92,7 @@ function UserMessageMentionChip(props: {
           </ContextChip>
         }
       />
-      <TooltipPopup>
+      <TooltipPopup className="pointer-events-auto">
         <WorkspaceEntryTooltip
           path={props.record.path}
           environmentId={ctx.activeThreadEnvironmentId}