Multiple problems on every single startup after recent releases

Grievous Angel · December 2023

Multi-decade quicken user here, going back to the DOS based app. It's never been more frustrating.

Recently, I've started encountering a couple of nagging startup issues.

Every time I open quicken, it "can't open specified file." It's the last file I opened. After I acknowledge, I just do "file" then open the only "recent" data file and it opens fine. I DO use quicken on multiple computers, and sync my quicken data directory using Onedrive, but this has never been a problem before. Just for giggles I set my Quicken file directory to "always be synced" (so local) to rule out the scenario where it has to sync before it opens. No dice. I've done a validate/repair on the file, including checking the box that has to do with authentication
Every time I try to sync, it asks me for my Quicken password. It almost never used to do this. Now it does it every time. Bonus points: it's now doing 2 factor. After that I put in my vault password.

This cropped up in the past few months. Kinda feels like it's been happening since the "classic" rebranding. Yes I've done a good bit of googling (which is why I did the file validation/repair/authentication checkbox thing.

Anyone else seeing this behavior and have you found any solutions?