Sorry for the late reply. The patch solves the problem for me, thanks!
Would be great to have this fixed.

On Sun, 2023-01-22 at 11:44 +0000, Ihor Radchenko wrote:
> * This is test
> SCHEDULED: <2023-01-28 Sat>
> 
> Then, M-: (setq org-extend-today-until 20)
> Then, C-c C-s on the heading above
> 
> What will happen if one tries to do "." or +1 or ++1. I find the
> current
> behavior rather disorienting. Could someone check what we promise in
> the
> Org manual, `org-read-date' docstring, `org-extend-today-until'
> docstring, and what actually happens in practice?
> 

Unless you see a bug that I'm not seeing, the behavior looks correct to
me (with the patch applied): The default date (when the user hasn't
entered anything) is the existing timestamp.  Then "." selects today
explicitly, "+" is relative to today, and "++" is relative to the
default date. That's exactly what's promised
inĀ https://orgmode.org/manual/The-date_002ftime-prompt.html and also in
the `org-read-date` doctring. (And I think it makes sense.)

Best,
Tim

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