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+;;; test-dwim-shell-security.el --- ERT tests for dwim-shell-config security functions -*- lexical-binding: t; -*-
+
+;; Author: Claude Code and cjennings
+;; Keywords: tests, dwim-shell, security
+
+;;; Commentary:
+;; ERT tests for security-related dwim-shell-config.el functions.
+;; Tests are organized into normal, boundary, and error cases.
+;;
+;; These tests verify that password-protected operations:
+;; - Do not expose passwords in process lists or command output
+;; - Use temporary files with restrictive permissions (mode 600)
+;; - Clean up temporary files after use (even on error)
+;; - Properly handle edge cases and errors
+
+;;; Code:
+
+(require 'ert)
+(require 'dwim-shell-config)
+(require 'testutil-general)
+
+;;; Setup and Teardown
+
+(defun test-dwim-shell-security-setup ()
+  "Set up test environment for dwim-shell-security tests."
+  (cj/create-test-base-dir)
+  ;; Create test PDF file
+  (setq test-pdf-file (expand-file-name "test.pdf" cj/test-base-dir))
+  ;; Create minimal valid PDF (this is a minimal PDF structure)
+  (with-temp-file test-pdf-file
+    (insert "%PDF-1.4\n")
+    (insert "1 0 obj\n<< /Type /Catalog /Pages 2 0 R >>\nendobj\n")
+    (insert "2 0 obj\n<< /Type /Pages /Kids [3 0 R] /Count 1 >>\nendobj\n")
+    (insert "3 0 obj\n<< /Type /Page /Parent 2 0 R /MediaBox [0 0 612 792] >>\nendobj\n")
+    (insert "xref\n0 4\n")
+    (insert "0000000000 65535 f\n")
+    (insert "0000000009 00000 n\n")
+    (insert "0000000058 00000 n\n")
+    (insert "0000000115 00000 n\n")
+    (insert "trailer\n<< /Size 4 /Root 1 0 R >>\nstartxref\n203\n%%EOF\n"))
+  ;; Create test files for archive operations
+  (setq test-file-1 (expand-file-name "file1.txt" cj/test-base-dir))
+  (setq test-file-2 (expand-file-name "file2.txt" cj/test-base-dir))
+  (with-temp-file test-file-1 (insert "Test content 1"))
+  (with-temp-file test-file-2 (insert "Test content 2")))
+
+(defun test-dwim-shell-security-teardown ()
+  "Clean up test environment after dwim-shell-security tests."
+  ;; Clean up test directory
+  (cj/delete-test-base-dir))
+
+;;; Helper Functions
+
+(defun test-dwim-check-temp-file-cleanup (pattern)
+  "Check that no temporary files matching PATTERN remain after operation."
+  (let ((temp-files (directory-files temporary-file-directory nil pattern)))
+    (should (null temp-files))))
+
+(defun test-dwim-check-file-permissions (file expected-mode)
+  "Check that FILE has EXPECTED-MODE permissions."
+  (when (file-exists-p file)
+    (should (equal (file-modes file) expected-mode))))
+
+;;; Normal Cases - PDF Password Protect
+
+(ert-deftest test-dwim-pdf-password-protect-creates-temp-file-normal ()
+  "Normal: PDF password protect creates temporary file with secure permissions."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let* ((captured-temp-file nil)
+             (original-make-temp-file (symbol-function 'make-temp-file)))
+        ;; Wrap make-temp-file to capture the temp file path
+        (cl-letf (((symbol-function 'make-temp-file)
+                   (lambda (&rest args)
+                     (setq captured-temp-file (apply original-make-temp-file args))
+                     captured-temp-file))
+                  ;; Mock read-passwd to avoid interactive prompts
+                  ((symbol-function 'read-passwd)
+                   (lambda (_prompt) "test-password"))
+                  ;; Mock dwim-shell-command-on-marked-files to check behavior
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description command &rest _args)
+                     ;; Verify temp file exists with correct permissions during execution
+                     (should (file-exists-p captured-temp-file))
+                     (test-dwim-check-file-permissions captured-temp-file #o600)
+                     ;; Verify password is in temp file, not in command
+                     (should (string-match-p captured-temp-file command))
+                     (should-not (string-match-p "test-password" command)))))
+          (cj/dwim-shell-commands-pdf-password-protect)
+          ;; Verify temp file is cleaned up after operation
+          (should-not (file-exists-p captured-temp-file))))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-pdf-password-protect-no-password-in-command-normal ()
+  "Normal: Password does not appear in shell command string."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let ((test-password "SuperSecret123!"))
+        (cl-letf (((symbol-function 'read-passwd)
+                   (lambda (_prompt) test-password))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description command &rest _args)
+                     ;; Password should NOT appear in command
+                     (should-not (string-match-p test-password command))
+                     ;; Command should reference password file
+                     (should (string-match-p "--password-file=" command)))))
+          (cj/dwim-shell-commands-pdf-password-protect)))
+    (test-dwim-shell-security-teardown)))
+
+;;; Normal Cases - PDF Password Unprotect
+
+(ert-deftest test-dwim-pdf-password-unprotect-creates-temp-file-normal ()
+  "Normal: PDF password unprotect creates temporary file with secure permissions."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let* ((captured-temp-file nil)
+             (original-make-temp-file (symbol-function 'make-temp-file)))
+        (cl-letf (((symbol-function 'make-temp-file)
+                   (lambda (&rest args)
+                     (setq captured-temp-file (apply original-make-temp-file args))
+                     captured-temp-file))
+                  ((symbol-function 'read-passwd)
+                   (lambda (_prompt) "test-password"))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description command &rest _args)
+                     (should (file-exists-p captured-temp-file))
+                     (test-dwim-check-file-permissions captured-temp-file #o600)
+                     (should (string-match-p captured-temp-file command))
+                     (should-not (string-match-p "test-password" command)))))
+          (cj/dwim-shell-commands-pdf-password-unprotect)
+          (should-not (file-exists-p captured-temp-file))))
+    (test-dwim-shell-security-teardown)))
+
+;;; Normal Cases - Create Encrypted Archive
+
+(ert-deftest test-dwim-create-encrypted-zip-uses-7z-normal ()
+  "Normal: Create encrypted archive uses 7z, not zip."
+  (skip-unless (executable-find "7z"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (cl-letf (((symbol-function 'read-passwd)
+                 (lambda (_prompt) "test-password"))
+                ((symbol-function 'read-string)
+                 (lambda (_prompt &optional _default) "test-archive"))
+                ((symbol-function 'dwim-shell-command-on-marked-files)
+                 (lambda (_description command &rest args)
+                   ;; Should use 7z, not zip
+                   (should (string-match-p "7z a" command))
+                   (should-not (string-match-p "zip -" command))
+                   ;; Should use AES encryption
+                   (should (string-match-p "-mhe=on" command))
+                   ;; Verify utils parameter is 7z
+                   (should (equal (plist-get args :utils) "7z")))))
+        (cj/dwim-shell-commands-create-encrypted-zip))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-create-encrypted-zip-no-password-in-command-normal ()
+  "Normal: Password does not appear in shell command string for archive creation."
+  (skip-unless (executable-find "7z"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let ((test-password "VerySecret456!"))
+        (cl-letf (((symbol-function 'read-passwd)
+                   (lambda (_prompt) test-password))
+                  ((symbol-function 'read-string)
+                   (lambda (_prompt &optional _default) "test-archive"))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description command &rest _args)
+                     ;; Password should NOT appear directly in command
+                     (should-not (string-match-p test-password command))
+                     ;; Should use cat to read from temp file
+                     (should (string-match-p "cat" command)))))
+          (cj/dwim-shell-commands-create-encrypted-zip)))
+    (test-dwim-shell-security-teardown)))
+
+;;; Normal Cases - Remove Archive Encryption
+
+(ert-deftest test-dwim-remove-zip-encryption-uses-7z-normal ()
+  "Normal: Remove archive encryption uses 7z for both extract and create."
+  (skip-unless (executable-find "7z"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (cl-letf (((symbol-function 'read-passwd)
+                 (lambda (_prompt) "test-password"))
+                ((symbol-function 'dwim-shell-command-on-marked-files)
+                 (lambda (_description command &rest args)
+                   ;; Should use 7z for both extract and archive
+                   (should (string-match-p "7z x" command))
+                   (should (string-match-p "7z a" command))
+                   ;; Verify utils parameter is 7z
+                   (should (equal (plist-get args :utils) "7z")))))
+        (cj/dwim-shell-commands-remove-zip-encryption))
+    (test-dwim-shell-security-teardown)))
+
+;;; Boundary Cases
+
+(ert-deftest test-dwim-pdf-password-empty-password-boundary ()
+  "Boundary: Empty password is accepted (though qpdf may reject it)."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let ((command-executed nil))
+        (cl-letf (((symbol-function 'read-passwd)
+                   (lambda (_prompt) ""))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description _command &rest _args)
+                     (setq command-executed t))))
+          (cj/dwim-shell-commands-pdf-password-protect)
+          ;; Function should accept empty password (tool may reject later)
+          (should command-executed)))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-pdf-password-special-characters-boundary ()
+  "Boundary: Password with special characters is properly handled."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let ((special-password "p@$$w0rd!#%^&*()"))
+        (cl-letf (((symbol-function 'read-passwd)
+                   (lambda (_prompt) special-password))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description command &rest _args)
+                     ;; Special characters should not appear in command
+                     (should-not (string-match-p (regexp-quote special-password) command)))))
+          (cj/dwim-shell-commands-pdf-password-protect)))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-archive-very-long-password-boundary ()
+  "Boundary: Very long password (1000+ chars) is properly handled."
+  (skip-unless (executable-find "7z"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let ((long-password (make-string 1000 ?x))
+            (captured-temp-file nil))
+        (cl-letf (((symbol-function 'read-passwd)
+                   (lambda (_prompt) long-password))
+                  ((symbol-function 'read-string)
+                   (lambda (_prompt &optional _default) "test"))
+                  ((symbol-function 'make-temp-file)
+                   (lambda (&rest args)
+                     (setq captured-temp-file (apply (symbol-function 'make-temp-file) args))
+                     captured-temp-file))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description _command &rest _args)
+                     ;; Verify password was written to temp file
+                     (with-temp-buffer
+                       (insert-file-contents captured-temp-file)
+                       (should (equal (buffer-string) long-password))))))
+          (cj/dwim-shell-commands-create-encrypted-zip)))
+    (test-dwim-shell-security-teardown)))
+
+;;; Error Cases
+
+(ert-deftest test-dwim-pdf-password-temp-file-cleanup-on-error-error ()
+  "Error: Temporary file is cleaned up even when command fails."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let* ((captured-temp-file nil)
+             (original-make-temp-file (symbol-function 'make-temp-file)))
+        (cl-letf (((symbol-function 'make-temp-file)
+                   (lambda (&rest args)
+                     (setq captured-temp-file (apply original-make-temp-file args))
+                     captured-temp-file))
+                  ((symbol-function 'read-passwd)
+                   (lambda (_prompt) "test-password"))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description _command &rest _args)
+                     ;; Simulate command failure
+                     (error "Command failed"))))
+          ;; Should error, but still clean up temp file
+          (should-error (cj/dwim-shell-commands-pdf-password-protect))
+          ;; Temp file should be cleaned up despite error
+          (should-not (file-exists-p captured-temp-file))))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-archive-temp-file-cleanup-on-error-error ()
+  "Error: Archive temp file cleaned up even when 7z command fails."
+  (skip-unless (executable-find "7z"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (let* ((captured-temp-file nil)
+             (original-make-temp-file (symbol-function 'make-temp-file)))
+        (cl-letf (((symbol-function 'make-temp-file)
+                   (lambda (&rest args)
+                     (setq captured-temp-file (apply original-make-temp-file args))
+                     captured-temp-file))
+                  ((symbol-function 'read-passwd)
+                   (lambda (_prompt) "test-password"))
+                  ((symbol-function 'read-string)
+                   (lambda (_prompt &optional _default) "test"))
+                  ((symbol-function 'dwim-shell-command-on-marked-files)
+                   (lambda (_description _command &rest _args)
+                     (error "7z command failed"))))
+          (should-error (cj/dwim-shell-commands-create-encrypted-zip))
+          (should-not (file-exists-p captured-temp-file))))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-pdf-password-temp-file-write-error-error ()
+  "Error: Error when unable to write to temporary file."
+  (skip-unless (executable-find "qpdf"))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (cl-letf (((symbol-function 'read-passwd)
+                 (lambda (_prompt) "test-password"))
+                ;; Mock make-temp-file to return a path that can't be written
+                ((symbol-function 'make-temp-file)
+                 (lambda (&rest _args) "/nonexistent/path/temp-file")))
+        ;; Should error when trying to write to non-existent path
+        (should-error (cj/dwim-shell-commands-pdf-password-protect)))
+    (test-dwim-shell-security-teardown)))
+
+(ert-deftest test-dwim-multiple-temp-file-cleanup-error ()
+  "Error: Multiple operations don't leave temp files behind."
+  (skip-unless (and (executable-find "qpdf") (executable-find "7z")))
+  (test-dwim-shell-security-setup)
+  (unwind-protect
+      (progn
+        ;; Track temp files before operations
+        (let ((initial-temp-files (directory-files temporary-file-directory nil "^qpdf-pass-\\|^7z-pass-")))
+          (cl-letf (((symbol-function 'read-passwd)
+                     (lambda (_prompt) "password"))
+                    ((symbol-function 'read-string)
+                     (lambda (_prompt &optional _default) "archive"))
+                    ((symbol-function 'dwim-shell-command-on-marked-files)
+                     (lambda (&rest _args) nil)))
+            ;; Run multiple operations
+            (cj/dwim-shell-commands-pdf-password-protect)
+            (cj/dwim-shell-commands-pdf-password-unprotect)
+            (cj/dwim-shell-commands-create-encrypted-zip)
+            (cj/dwim-shell-commands-remove-zip-encryption))
+          ;; Check no new temp files remain
+          (let ((final-temp-files (directory-files temporary-file-directory nil "^qpdf-pass-\\|^7z-pass-")))
+            (should (equal (length final-temp-files) (length initial-temp-files))))))
+    (test-dwim-shell-security-teardown)))
+
+(provide 'test-dwim-shell-security)
+;;; test-dwim-shell-security.el ends here