diff --git a/.changeset/run-directory-signal-cleanup.md b/.changeset/run-directory-signal-cleanup.md
new file mode 100644
index 00000000..4a273a6c
--- /dev/null
+++ b/.changeset/run-directory-signal-cleanup.md
@@ -0,0 +1,5 @@
+---
+"@taskless/cli": patch
+---
+
+Interrupting `taskless check` with Ctrl-C or SIGTERM now reliably removes the run's `.taskless/.run/` directory. Before this fix, a log entry that was still being written could recreate its file mid-removal, and the directory was left behind until a later run swept it.
diff --git a/packages/cli/src/rules/run-directory.ts b/packages/cli/src/rules/run-directory.ts
index 4c864538..635f5540 100644
--- a/packages/cli/src/rules/run-directory.ts
+++ b/packages/cli/src/rules/run-directory.ts
@@ -363,8 +363,17 @@ export async function openRun(
       return;
     }
     if (!preserve) {
+      // A queued append may be mid-flight on a worker thread, and can
+      // recreate its log between the unlinks and the final rmdir, which
+      // then fails ENOTEMPTY. Retrying removes the late file; the worker
+      // finishes while this thread waits. Bounded at 150ms.
       try {
-        rmSync(path, { recursive: true, force: true });
+        rmSync(path, {
+          recursive: true,
+          force: true,
+          maxRetries: 5,
+          retryDelay: 10,
+        });
       } catch {
         // The next run's sweep removes it.
       }