If I am typing, and then type “Cmd-D” to delete the paragraph, then that paragraph is lost, and the undo stack restores something older.
If I wait about 1 or 2 seconds, the effect doesn’t happen. It only seems to happen if you trigger the command quickly after typing your last character(s).
(Often people make bug reports that should have been posted in help. This seems to be the opposite. I think it would have been better for you to fill out the template and report a bug. I’m just going to move it to Bug Reports.)
I think it’s better if your rewrite this as a BR and you are specific about what specifically should be handled differently. The undo logic is very complex.
If I type quickly and then use Cmd-D then the thing I typed gets clumped into the undo stack, and gets lost and can’t be redone.
Cmd-fn-delete (Cmd-Backspace) clumps into the undo stack, but it seems to redo just fine. (I think this is what OP was writing about. But I can only seem to reproduce with Cmd-D.)