> If you love git so much, try to do a squash merge to the main, then do some other changes in your branch, and try to merge again. Have fun solving all the merge conflicts that actually shouldn't be there.

Why I should want to do it? It feels unnatural. What problem you are trying to solve by this workflow?

I'm very curious how your favorite VCS handle this case.

> try to do a squash merge to the main, then do some other changes in your branch, and try to merge again

For this situation, at the end just do:

git rebase -i main

And delete all of the commits that you included in your squashed commit. If you want to preserve your detailed history you can create a new branch for the rebase like so:

git checkout -b mybranch-rebase && git rebase -i main

> do a squash merge to the main

If you want Git to continue keeping track of your commits, don’t squash-merge them.

Squash merging loses valuable history in general and use of it is a sign that commits on source branches are being made carelessly.

(That said, if I had to do this, I’d rebase off of the squash before merging again and have no problems.)

I would just delete the branch after merge to the main and then create a new branch from main.