Consider:
* Test :LOGBOOK: CLOCK: [2023-02-19 Sun 22:30]--[2023-02-20 Mon 00:35] => 2:05 :END: Hitting C-S-up/down in the first time stamp does not preserver duration, and can lead to negative durations, which "break" the clock. The same keystrokes work as intended in the second timestamp. Emacs : GNU Emacs 28.2 (build 1, x86_64-apple-darwin21.6.0, Carbon Version 165 AppKit 2113.6) of 2022-11-01 Package: Org mode version 9.6.1 (release_N/A-N/A-747e60 @ /Users/[]/.emacs.d/elpa/org-9.6.1.0.20230218.123114/) current state: ============== (setq org-link-elisp-confirm-function 'yes-or-no-p org-bibtex-headline-format-function #[257 "\300\236A\207" [:title] 3 "\n\n(fn ENTRY)"] org-persist-after-read-hook '(org-element--cache-persist-after-read) org-export-before-parsing-hook '(org-attach-expand-links) org-cycle-tab-first-hook '(org-babel-hide-result-toggle-maybe org-babel-header-arg-expand) org-archive-hook '(org-attach-archive-delete-maybe) org-cycle-hook '(org-cycle-hide-archived-subtrees org-cycle-show-empty-lines org-cycle-optimize-window-after-visibility-change org-cycle-display-inline-images) org-persist-before-read-hook '(org-element--cache-persist-before-read) org-mode-hook '(#[0 "\301\211\207" [imenu-create-index-function org-imenu-get-tree] 2] #[0 "\300\301\302\303\304$\207" [add-hook change-major-mode-hook org-fold-show-all append local] 5] #[0 "\300\301\302\303\304$\207" [add-hook change-major-mode-hook org-babel-show-result-all append local] 5] org-babel-result-hide-spec org-babel-hide-all-hashes) org-confirm-shell-link-function 'yes-or-no-p outline-isearch-open-invisible-function 'outline-isearch-open-invisible org-agenda-before-write-hook '(org-agenda-add-entry-text) org-src-mode-hook '(org-src-babel-configure-edit-buffer org-src-mode-configure-edit-buffer) org-confirm-elisp-link-function 'yes-or-no-p org-speed-command-hook '(org-speed-command-activate org-babel-speed-command-activate) org-persist-directory "/var/folders/by/19mt78cj63v5_tslqh826g7w0000gn/T/org-persist-XBsel1" org-fold-core-isearch-open-function 'org-fold--isearch-reveal org-persist-before-write-hook '(org-element--cache-persist-before-write) org-tab-first-hook '(org-babel-hide-result-toggle-maybe org-babel-header-arg-expand) org-link-shell-confirm-function 'yes-or-no-p org-babel-pre-tangle-hook '(save-buffer) org-agenda-loop-over-headlines-in-active-region nil org-occur-hook '(org-first-headline-recenter) org-metadown-hook '(org-babel-pop-to-session-maybe) org-link-parameters '(("attachment" :follow org-attach-follow :complete org-attach-complete-link) ("id" :follow org-id-open) ("eww" :follow org-eww-open :store org-eww-store-link) ("rmail" :follow org-rmail-open :store org-rmail-store-link) ("mhe" :follow org-mhe-open :store org-mhe-store-link) ("irc" :follow org-irc-visit :store org-irc-store-link :export org-irc-export) ("info" :follow org-info-open :export org-info-export :store org-info-store-link :insert-description org-info-description-as-command) ("gnus" :follow org-gnus-open :store org-gnus-store-link) ("docview" :follow org-docview-open :export org-docview-export :store org-docview-store-link) ("bibtex" :follow org-bibtex-open :store org-bibtex-store-link) ("bbdb" :follow org-bbdb-open :export org-bbdb-export :complete org-bbdb-complete-link :store org-bbdb-store-link) ("w3m" :store org-w3m-store-link) ("doi" :follow org-link-doi-open :export org-link-doi-export) ("file+sys") ("file+emacs") ("shell" :follow org-link--open-shell) ("news" :follow #[514 "\301\300\302Q\"\207" ["news" browse-url ":"] 6 "\n\n(fn URL ARG)"] ) ("mailto" :follow #[514 "\301\300\302Q\"\207" ["mailto" browse-url ":"] 6 "\n\n(fn URL ARG)"] ) ("https" :follow #[514 "\301\300\302Q\"\207" ["https" browse-url ":"] 6 "\n\n(fn URL ARG)"] ) ("http" :follow #[514 "\301\300\302Q\"\207" ["http" browse-url ":"] 6 "\n\n(fn URL ARG)"] ) ("ftp" :follow #[514 "\301\300\302Q\"\207" ["ftp" browse-url ":"] 6 "\n\n(fn URL ARG)"] ) ("help" :follow org-link--open-help :store org-link--store-help) ("file" :complete org-link-complete-file) ("elisp" :follow org-link--open-elisp)) org-metaup-hook '(org-babel-load-in-session-maybe) )