Double upgrade and password

I started using the subscription version of quicken for windows in March/April. My system is on R28.18. Just like the old traditional software version the product prompts to update and I run through that part. Then the upgrade just becomes annoying and not as friendly as the traditional software version.

I have to log in to quicken from within the product twice to get prompted to download the update. The first couple of times I did download and install the update a second time. I think that requires another log in to the program. Then I try to run the account update and my passwords are blank. I know that storing the passwords in the program is not safe but it made the feature easy to use. So I have to go to the password manager and copy / paste those back in and click save. Everything works but is a little slow until the next update and the process is repeated.

How do I update the product without the loss of passwords?