What the judge is doing is a mystery to me. It’s clear from the 302 that Flynn was doing regular outreach.
My totally amateur interpretation. The judge thinks he has a lot to say and do re the prosecution, but unless Flynn withdraws his plea he is forced to follow through with the sentencing. It is a very public trial. Quite a few people are aware that Flynn is pleading guilty to something that was not a crime. The judge does not like to be put in the role of the bad judge.
(I was about to write a “latter day Pontius Pilate” but that would have put Gen Flynn in a much better light than I think he deserves. )
Delayed 90 days.