sting.startup...@icloud.com writes:

> 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.

Thanks for reporting.
Fixed, on bugfix.
https://git.savannah.gnu.org/cgit/emacs/org-mode.git/commit/?id=7a90f596d

-- 
Ihor Radchenko // yantar92,
Org mode contributor,
Learn more about Org mode at <https://orgmode.org/>.
Support Org development at <https://liberapay.com/org-mode>,
or support my work at <https://liberapay.com/yantar92>

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