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+;;; test-chime-extract-time.el --- Tests for chime--extract-time -*- lexical-binding: t; -*-
+
+;; Copyright (C) 2024 Craig Jennings
+
+;; Author: Craig Jennings <c@cjennings.net>
+
+;; This program is free software: you can redistribute it and/or modify
+;; it under the terms of the GNU General Public License as published by
+;; the Free Software Foundation, either version 3 of the License, or
+;; (at your option) any later version.
+
+;; This program is distributed in the hope that it will be useful,
+;; but WITHOUT ANY WARRANTY; without even the implied warranty of
+;; MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+;; GNU General Public License for more details.
+
+;; You should have received a copy of the GNU General Public License
+;; along with this program.  If not, see <http://www.gnu.org/licenses/>.
+
+;;; Commentary:
+
+;; Unit tests for chime--extract-time function.
+;; Tests cover normal cases, boundary cases, and error cases.
+
+;;; Code:
+
+;; Initialize package system for batch mode
+(when noninteractive
+  (package-initialize))
+
+(require 'ert)
+
+;; Load dependencies required by chime
+(require 'dash)
+(require 'alert)
+(require 'async)
+(require 'org-agenda)
+
+;; Load chime from parent directory
+(load (expand-file-name "../chime.el") nil t)
+
+;; Load test utilities
+(require 'testutil-general (expand-file-name "testutil-general.el"))
+
+;;; Setup and Teardown
+
+(defun test-chime-extract-time-setup ()
+  "Setup function run before each test."
+  (chime-create-test-base-dir))
+
+(defun test-chime-extract-time-teardown ()
+  "Teardown function run after each test."
+  (chime-delete-test-base-dir))
+
+;;; Normal Cases
+
+(ert-deftest test-chime-extract-time-scheduled-timestamp-extracted ()
+  "Test that SCHEDULED timestamp is extracted correctly."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "<2025-10-24 Fri 14:30>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (= (length result) 1))
+              (should (equal (caar result) "<2025-10-24 Fri 14:30>"))
+              (should (listp (cdar result)))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-deadline-timestamp-extracted ()
+  "Test that DEADLINE timestamp is extracted correctly."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 16:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (= (length result) 1))
+              (should (equal (caar result) "<2025-10-24 Fri 16:00>"))
+              (should (listp (cdar result)))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-plain-timestamp-extracted ()
+  "Test that plain TIMESTAMP is extracted correctly."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* Test Event\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "TIMESTAMP"))
+                         "<2025-10-24 Fri 10:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (= (length result) 1))
+              (should (equal (caar result) "<2025-10-24 Fri 10:00>"))
+              (should (listp (cdar result)))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-multiple-timestamps-all-extracted ()
+  "Test that multiple timestamps are all extracted."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "<2025-10-24 Fri 14:30>")
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 16:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (= (length result) 2))
+              ;; Check both timestamps are present
+              (should (--some (equal (car it) "<2025-10-24 Fri 14:30>") result))
+              (should (--some (equal (car it) "<2025-10-24 Fri 16:00>") result))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-all-three-timestamp-types-extracted ()
+  "Test that all three timestamp types can be extracted together."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Complex Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "<2025-10-24 Fri 09:00>")
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 17:00>")
+                        ((and (equal pom marker) (equal property "TIMESTAMP"))
+                         "<2025-10-24 Fri 12:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (= (length result) 3))))))
+    (test-chime-extract-time-teardown)))
+
+;;; Boundary Cases
+
+(ert-deftest test-chime-extract-time-no-timestamps-returns-empty ()
+  "Test that entry with no timestamps returns empty list."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       nil)))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (= (length result) 0))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-only-scheduled-extracted ()
+  "Test that only SCHEDULED is extracted when others are missing."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "<2025-10-24 Fri 14:30>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (= (length result) 1))
+              (should (equal (caar result) "<2025-10-24 Fri 14:30>"))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-only-deadline-extracted ()
+  "Test that only DEADLINE is extracted when others are missing."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 16:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (= (length result) 1))
+              (should (equal (caar result) "<2025-10-24 Fri 16:00>"))))))
+    (test-chime-extract-time-teardown)))
+
+;;; Error Cases
+
+(ert-deftest test-chime-extract-time-malformed-timestamp-returns-nil-cdr ()
+  "Test that malformed timestamps return cons with nil cdr."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "not-a-valid-timestamp")
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 16:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              ;; Should return both, but malformed one has nil cdr
+              (should (= (length result) 2))
+              ;; Find the malformed timestamp result
+              (let ((malformed (--find (equal (car it) "not-a-valid-timestamp") result)))
+                (should malformed)
+                (should-not (cdr malformed)))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-day-wide-timestamp-returns-nil-cdr ()
+  "Test that day-wide timestamps (no time) return cons with nil cdr."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "<2025-10-24 Fri>")  ; Day-wide, no time
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 16:00>")  ; Has time
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              ;; Should return both timestamps
+              (should (= (length result) 2))
+              ;; Day-wide timestamp has nil cdr
+              (let ((day-wide (--find (equal (car it) "<2025-10-24 Fri>") result)))
+                (should day-wide)
+                (should-not (cdr day-wide)))
+              ;; Timed timestamp has valid cdr
+              (let ((timed (--find (equal (car it) "<2025-10-24 Fri 16:00>") result)))
+                (should timed)
+                (should (cdr timed)))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-empty-timestamp-string-returns-nil-cdr ()
+  "Test that empty timestamp strings return cons with nil cdr."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "")
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "<2025-10-24 Fri 16:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              ;; Should return both entries
+              (should (= (length result) 2))
+              ;; Empty string has nil cdr
+              (let ((empty (--find (equal (car it) "") result)))
+                (should empty)
+                (should-not (cdr empty)))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-all-malformed-returns-cons-with-nil-cdrs ()
+  "Test that all malformed timestamps return cons with nil cdrs."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* TODO Test Task\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "SCHEDULED"))
+                         "not-valid")
+                        ((and (equal pom marker) (equal property "DEADLINE"))
+                         "also-not-valid")
+                        ((and (equal pom marker) (equal property "TIMESTAMP"))
+                         "<2025-10-24 Fri>")  ; Day-wide
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              ;; Should return 3 entries, all with nil cdr
+              (should (= (length result) 3))
+              (should (--every (not (cdr it)) result))))))
+    (test-chime-extract-time-teardown)))
+
+;;; org-gcal Integration Tests
+
+(ert-deftest test-chime-extract-time-org-gcal-time-range-format ()
+  "Test extraction of org-gcal style timestamp with time range.
+org-gcal uses format like <2025-10-24 Fri 17:30-18:00> with HH:MM-HH:MM range."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* Testing Round Trip\n")
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "TIMESTAMP"))
+                         "<2025-10-24 Fri 17:30-18:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (>= (length result) 1))
+              ;; Should extract the timestamp string
+              (should (equal (caar result) "<2025-10-24 Fri 17:30-18:00>"))
+              ;; Should have parsed time value (not nil)
+              (should (listp (cdar result)))
+              (should (cdar result))))))
+    (test-chime-extract-time-teardown)))
+
+(ert-deftest test-chime-extract-time-org-gcal-in-drawer ()
+  "Test extraction of timestamp inside org-gcal drawer.
+org-gcal stores timestamps in :org-gcal: drawers which should still be detected."
+  (test-chime-extract-time-setup)
+  (unwind-protect
+      (with-temp-buffer
+        (org-mode)
+        (insert "* Testing Chime!\n")
+        (insert ":PROPERTIES:\n")
+        (insert ":ETag:     \"3522688202987102\"\n")
+        (insert ":calendar-id: user@example.com\n")
+        (insert ":entry-id: abc123/user@example.com\n")
+        (insert ":org-gcal-managed: gcal\n")
+        (insert ":END:\n")
+        (insert ":org-gcal:\n")
+        (insert "<2025-10-24 Fri 17:30-18:00>\n")
+        (insert ":END:\n")
+        (goto-char (point-min))
+        (let ((marker (copy-marker (point))))
+          (cl-letf (((symbol-function 'org-entry-get)
+                     (lambda (pom property &optional inherit literal-nil)
+                       (cond
+                        ((and (equal pom marker) (equal property "TIMESTAMP"))
+                         "<2025-10-24 Fri 17:30-18:00>")
+                        (t nil)))))
+            (let ((result (chime--extract-time marker)))
+              (should (listp result))
+              (should (>= (length result) 1))
+              (should (equal (caar result) "<2025-10-24 Fri 17:30-18:00>"))
+              (should (cdar result))))))
+    (test-chime-extract-time-teardown)))
+
+(provide 'test-chime-extract-time)
+;;; test-chime-extract-time.el ends here