Repeated login requests--a theory
I keep my data file in Dropbox, and access it from two different computers. Things work fine on one, but oddly on the other.
On computer A, a Win11 laptop, everything works as it should: I get a Quicken login request now and then, but mostly when I do OSU I just get the Vault authentication request. Also, update installs work flawlessly.
On computer B, a Win11 desktop, I get the Quicken login dialog every time I do OSU the first time during a session, followed by the Vault authentication; if I close the file and open again, I have to do the Quicken login again. Also, although some update installs work fine, about half of them fail with an "administrator privileges required" error even though the account is an admin account, but if I restart Quicken using "run as administrator" the install works fine, albeit after Quicken warning me there's no such thing as "run as administrator".
There's one key difference between the two computers. Computer A just has one disk drive, so the data file (from Dropbox) and Quicken's config files (in AppData|Roaming|Quicken|config) are on the same drive. Computer B has two drives, and whereas Quicken's config files are on the C drive (an SSD), my Dropbox files, including the Quicken datafile, are on the D drive (a spinning terabyte drive).
Here's my theory why Computer B misbehaves: I think that when I do a Quicken authentication, Quicken records the resulting authentication ticket in a config file called "authslots" on the C drive, and lets me use my data file. However, when I re-open the file, I think Quicken goes looking for its config files on the same drive as the data file—that is, the D drive—and when it doesn't find any it forces a reauthentication.
Minor evidence for this is that if I open my datafile on Computer B, do something, and then close it, when I open the same file on Computer A I don't have to reauthenticate to Quicken, presumably because Quicken finds the authslots file on the same drive where it got the datafile, namely C.
If this is right, then the obvious fix for the problem is either to have Quicken know the full path for the config files, or to store the auth tickets in the same location as the datafile.