I just tried replying to an indent below a bullet, expecting an additional indent. This was the result -- I would have expected an additional indent. Is this the intended behaviour?
Topic on Talk:Talk pages project/Replying/Flow
Usually an additional indent would be added – I think the tool becomes confused because there's no signature after the previous comment ("More generally…"), and it treats both paragraphs ("More generally…" and "Looking over your question…") as a single comment with incorrect indentation, and guesses wrong how to indent the reply.
It's quite common to see indented responses without signatures; two of the reviews I've posted on en-wiki recently were with editors who did not sign each indented response. I think it would be worth trying to make the tool handle this situation. The workaround is easy, at least; I can see the indent level and just add a colon.
The Reply tool used to calculate the indentation according to the last line of the comment. Then editors complained, so they changed it to set the punctuation according to the first line of the comment. What you encountered is the result of those editors' request. If we'd stuck with the original settings, your comment would have worked like you expected. (However, others wouldn't.)
How about making that a user preference?
Because we want it both ways. We want to indent according to the first when that makes sense, and to the last when that makes sense.
I think the solution is to let us manually override the software's best guess. That's primarily phab:T265750.