Max Nikulin <manikulin@gmail.com> writes:

>> I am unable to reproduce on the latest Org.
>
> Thank you, Ihor. I have checked it once more for current main HEAD 
> 2bd34edb64. I can reproduce it using the provided steps in Emacs-26, but 
> not in Emacs-27.
>
> Unless there is a reason to suspect something weird underneath, the 
> issue should be considered with rather low priority. Anyway, I have 
> added trailing newline to generated content and mostly use org-capture 
> with org-protocol for communication between applications.

Thanks for the extra info!
I managed to reproduce using Emacs 26 and it is a real problem with some
edge case in org-indent. The problem is masked by
combine-after-change-calls that is used since Emacs 27 but replaced by a
placeholer in Emacs 26.

The fix is attached. Let me know if it also works on your side.

Best,
Ihor