diff --git a/apps/web/src/components/files/filePath.test.ts b/apps/web/src/components/files/filePath.test.ts
index 22cb582493df2..3bc371b5c1ab9 100644
--- a/apps/web/src/components/files/filePath.test.ts
+++ b/apps/web/src/components/files/filePath.test.ts
@@ -1,6 +1,12 @@
 import { describe, expect, it } from "vite-plus/test";
 
-import { fileBreadcrumbChildren, fileBreadcrumbs, retainedBreadcrumbTrail } from "./filePath";
+import {
+  breadcrumbPathOf,
+  fileBreadcrumbChildren,
+  fileBreadcrumbs,
+  isListableHostFolder,
+  retainedBreadcrumbTrail,
+} from "./filePath";
 
 describe("fileBreadcrumbs", () => {
   it("starts host paths outside the workspace at the filesystem root", () => {
@@ -20,6 +26,26 @@ describe("fileBreadcrumbs", () => {
       "\\\\server\\share\\report.md",
     ]);
   });
+
+  it("builds home-relative breadcrumbs with navigable folders", () => {
+    expect(fileBreadcrumbs("t3code", "~/.claude/CLAUDE.md")).toEqual([
+      { label: "~", path: "~/", kind: "directory" },
+      { label: ".claude", path: "~/.claude", kind: "directory" },
+      { label: "CLAUDE.md", path: "~/.claude/CLAUDE.md", kind: "file" },
+    ]);
+    expect(isListableHostFolder("~/")).toBe(true);
+    expect(isListableHostFolder("~/.claude")).toBe(true);
+  });
+
+  it("keeps a project folder named ~ inside the project", () => {
+    expect(fileBreadcrumbs("t3code", "~").map((crumb) => crumb.path)).toEqual(["", "~"]);
+  });
+});
+
+describe("breadcrumbPathOf", () => {
+  it("keeps the home root listable", () => {
+    expect(breadcrumbPathOf("~/")).toBe("~/");
+  });
 });
 
 describe("fileBreadcrumbChildren", () => {
diff --git a/apps/web/src/components/files/filePath.ts b/apps/web/src/components/files/filePath.ts
index 76e10839bb2c8..f9f3c9a5ac40a 100644
--- a/apps/web/src/components/files/filePath.ts
+++ b/apps/web/src/components/files/filePath.ts
@@ -23,7 +23,8 @@ export function fileBreadcrumbs(projectName: string, relativePath: string): File
       return {
         label: part,
         // A bare drive (`C:`) means the drive's current directory; its root is `C:\`.
-        path: /^[A-Za-z]:$/.test(path) ? `${path}\\` : path,
+        // A bare `~` is not a host path; the home folder is `~/`.
+        path: /^[A-Za-z]:$/.test(path) ? `${path}\\` : hostPath && path === "~" ? "~/" : path,
         kind: index === parts.length - 1 ? ("file" as const) : ("directory" as const),
       };
     }),