I think this may be a subtlety of Sage 300, but I don't know. I have some converted Sage 300 data including a lot of quotes from up to November 2019. I can't print any of them out. When I enter a new quote, as of today 7/30/2020 it prints fine. I definitely checked the "reprint quotes already printed" box. 

When I go into the system it was converted from, I can print quotes as old as April 2020 but nothing earlier. That system has periods locked up to and including 4/2020.

FWIW, This user does day-end every day.

So, what might be the problem here?