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diff --git a/tests/test-transcription-log-cleanup.el b/tests/test-transcription-log-cleanup.el
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+;;; test-transcription-log-cleanup.el --- Tests for log cleanup logic -*- lexical-binding: t; -*-
+
+;;; Commentary:
+;; Tests for cj/--should-keep-log function
+;; Categories: Normal cases, Boundary cases
+
+;;; Code:
+
+(require 'ert)
+(require 'transcription-config)
+
+;; ----------------------------- Normal Cases ----------------------------------
+
+(ert-deftest test-cj/--should-keep-log-success-keep-disabled ()
+  "Test that logs are deleted on success when keep-log is nil."
+  (let ((cj/transcription-keep-log-when-done nil))
+    (should-not (cj/--should-keep-log t))))
+
+(ert-deftest test-cj/--should-keep-log-success-keep-enabled ()
+  "Test that logs are kept on success when keep-log is t."
+  (let ((cj/transcription-keep-log-when-done t))
+    (should (cj/--should-keep-log t))))
+
+(ert-deftest test-cj/--should-keep-log-error-keep-disabled ()
+  "Test that logs are always kept on error, even if keep-log is nil."
+  (let ((cj/transcription-keep-log-when-done nil))
+    (should (cj/--should-keep-log nil))))
+
+(ert-deftest test-cj/--should-keep-log-error-keep-enabled ()
+  "Test that logs are kept on error when keep-log is t."
+  (let ((cj/transcription-keep-log-when-done t))
+    (should (cj/--should-keep-log nil))))
+
+;; ----------------------------- Boundary Cases --------------------------------
+
+(ert-deftest test-cj/--should-keep-log-default-behavior ()
+  "Test default behavior (should not keep on success)."
+  ;; Default is nil based on defcustom
+  (let ((cj/transcription-keep-log-when-done nil))
+    (should-not (cj/--should-keep-log t))
+    (should (cj/--should-keep-log nil))))
+
+(provide 'test-transcription-log-cleanup)
+;;; test-transcription-log-cleanup.el ends here