The two most recent upsets were GPG deliberately breaking a whole bunch of compatability, meaning newer versions will not decrypt older files. For people who use GPG for e.g. securing transferred documents that might be called in court, it's pretty upsetting, to put it mildly, that the maintainer has told us we're on our own if we want to be able to access old files[1]. Since this is one of the core uses for GPG it's generated a lot of angst.
The more obnoxious one for me is going out of his way to break a whole bunch of GPG integration, complete with acerbic error messages for people who had been relying on it. Making encryption harder to use will not improve security.
[1] Sure, you can keep old sources around and hope GPG 1.x will still build 10 years from now, but that's a bit of a gamble.