diff --git a/.changeset/tidy-voles-glide.md b/.changeset/tidy-voles-glide.md
new file mode 100644
index 000000000..92bd662ce
--- /dev/null
+++ b/.changeset/tidy-voles-glide.md
@@ -0,0 +1,5 @@
+---
+type: Fixed
+pr: 2235
+---
+**`commit_docs` no longer silently disables on CRLF `.gitignore` repos** — git check-ignore falsely reports a trailing-slash path (e.g. `.planning/`) as ignored when the .gitignore has CRLF line endings with blank lines. isGitIgnored now strips trailing slashes before querying, so the false positive cannot occur. (#2206)
diff --git a/src/config-loader.cts b/src/config-loader.cts
index 2384f60a2..c5216dfb5 100644
--- a/src/config-loader.cts
+++ b/src/config-loader.cts
@@ -175,10 +175,14 @@ interface ParsedConfig {
 const _gitIgnoredCache = new Map<string, boolean>();
 
 function isGitIgnored(cwd: string, targetPath: string): boolean {
-  const key = cwd + '::' + targetPath;
+  // #2206: strip trailing slashes — `git check-ignore` has a quirk where a
+  // CRLF .gitignore with blank lines falsely reports a trailing-slash path
+  // (e.g. `.planning/`) as ignored. Normalizing here protects every call site.
+  const normalized = targetPath.replace(/\/+$/, '');
+  const key = cwd + '::' + normalized;
   if (_gitIgnoredCache.has(key)) return _gitIgnoredCache.get(key)!;
   // --no-index checks .gitignore rules regardless of whether the file is tracked.
-  const result = execGit(['check-ignore', '-q', '--no-index', '--', targetPath], { cwd });
+  const result = execGit(['check-ignore', '-q', '--no-index', '--', normalized], { cwd });
   const ignored = result.exitCode === 0;
   _gitIgnoredCache.set(key, ignored);
   return ignored;