Thanks everyone for your responses. I responded during the weekend but my email was too big and got rejected. It's not relevant anymore.
Pointing out the fact that the dot-stuffing works on the two sides (adding then removing) shows that in the current scenario, the issue is either caused by the sender or by us, and not between us and Gmail. I still don't have the root cause of this as we are investigating it. The sender claims they are adding an extra dot when needed, and the aiosmtpd library on which we relies does remove them. I'm starting to wonder if the issue isn't related to something else. I'm discussing with the sender on ways to get a raw email from them and check where the email starts breaking the DKIM signature. I'll keep you updated once we get to the root of the issue for those who are interested to find out. Have a nice week!
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