From f915320914d1bc446e60cbcfe4cd7d75bad4dc2a Mon Sep 17 00:00:00 2001
From: jorvarea <47249803+jorvarea@users.noreply.github.com>
Date: Sat, 15 Aug 2026 14:10:32 +0200
Subject: [PATCH] fix(web): keep the final segment of directory paths with a
 trailing separator (#5460)

Co-authored-by: jorvarea <jorvarea@users.noreply.github.com>
---
 apps/web/src/markdown-links.test.ts | 25 +++++++++++++++++++++++++
 apps/web/src/markdown-links.ts      |  8 ++++++--
 2 files changed, 31 insertions(+), 2 deletions(-)

diff --git a/apps/web/src/markdown-links.test.ts b/apps/web/src/markdown-links.test.ts
index 9fc29613867276f00bdea7d460b2df1786883ae3..f7c507c178f9e50c7f8882e54e72efecba42b6ae 100644
--- a/apps/web/src/markdown-links.test.ts
+++ b/apps/web/src/markdown-links.test.ts
@@ -273,3 +273,28 @@ describe("resolveInlineCodeFileLinkMeta", () => {
     expect(resolveInlineCodeFileLinkMeta(".plans/worktree-management-v1.md")).toBeNull();
   });
 });
+
+describe("directory paths with a trailing separator", () => {
+  it("keeps the final segment for a POSIX directory path", () => {
+    expect(resolveMarkdownFileLinkMeta("/tmp/favicons/", "/repo/project")).toMatchObject({
+      basename: "favicons",
+    });
+  });
+
+  it("keeps the final segment for a Windows directory path", () => {
+    expect(
+      resolveMarkdownFileLinkMeta("C:\\Users\\kelchm\\.claude\\", "/repo/project"),
+    ).toMatchObject({ basename: ".claude" });
+  });
+
+  it("matches the label of the same path without a trailing separator", () => {
+    const withSlash = resolveMarkdownFileLinkMeta("/tmp/favicons/", "/repo/project");
+    const withoutSlash = resolveMarkdownFileLinkMeta("/tmp/favicons", "/repo/project");
+    expect(withSlash?.basename).toBe(withoutSlash?.basename);
+  });
+
+  it("does not produce an empty label for the filesystem root", () => {
+    const meta = resolveMarkdownFileLinkMeta("/tmp/", "/repo/project");
+    expect(meta?.basename).not.toBe("");
+  });
+});
diff --git a/apps/web/src/markdown-links.ts b/apps/web/src/markdown-links.ts
index a6dba941b8aceb53eb8aa37decea69b0bbfaac0e..e74bd170117f24a249336e69f69bdc617988dfaf 100644
--- a/apps/web/src/markdown-links.ts
+++ b/apps/web/src/markdown-links.ts
@@ -359,8 +359,12 @@ export function resolveInlineCodeFileLinkMeta(
 }
 
 function basenameOfPath(path: string): string {
-  const separatorIndex = Math.max(path.lastIndexOf("/"), path.lastIndexOf("\\"));
-  return separatorIndex >= 0 ? path.slice(separatorIndex + 1) : path;
+  // A trailing separator is a valid way to write a directory, so trim it before
+  // taking the final segment. Without this the segment reads as empty and the
+  // chip renders with no label at all.
+  const trimmed = path.replace(/[/\\]+$/, "") || path;
+  const separatorIndex = Math.max(trimmed.lastIndexOf("/"), trimmed.lastIndexOf("\\"));
+  return separatorIndex >= 0 ? trimmed.slice(separatorIndex + 1) : trimmed;
 }
 
 function workspaceRelativePath(path: string, workspaceRoot: string | undefined): string | null {
-- 
2.54.0