Why do I have to sign into my quicken classic account each time I open the software [Edited]

Hello @jgplbw,

Thanks for reaching out! This repeated sign-in prompt can happen if there’s an authentication issue with your Quicken ID. Please review this support article that covers this scenario in detail, and follow the steps provided below (which can also be found within the article).

1. Download the latest update here if you have not done so already.
2. After completing the update, open Quicken.
3. Hold the Control key and select File menu > Validate and Repair File.
4. Check the Validate file box and click OK. 

If initiated correctly, the Validate file checkbox will also show the message "Authentication block will be fixed" as pictured above.

If the issue persists

1. If you don't see or can't get to the Edit menu on the upper left, close the sign in window.  You may have to close it several times before you can see the Edit option.
2. Click on the Edit Menu, and select Preferences.
3. In the left panel, select Quicken ID & Cloud Accounts.
4. Click Sign in as a different user.
5. Type "yes" as prompted, and click Sign Out.
6. Sign back in with your Quicken ID.

Hope this helps!

Hello again,

Checking in once more before this thread is closed.
Let us know if you still need assistance.

Thank you!