Why can't outlook remember my password? from Nov 29 radio show

I would put under today’s show but it is not on here yet. The 2004 update to windows introduced bugs as always. this one was very frustrating as when Outlook forgot the password I also had to do the two-factor for gmail. when I switched to an aol account with pop3 it still happened, only the app password no longer worked and I had to go get a new one from aol.com each time the loss happened. I was saved from my misery by a guy named Tavis who provided ‘solution #2’ in this article:

funny thing is I think you covered this one in a previous show???

Outlook isn’t updated with Windows 2004.

However, Outlook does get confused when there are multiple accounts and asks for passwords, you need to ensure you give the right username and password for each account (and click the remember password box). It has a habit of asking for the first username and password and then using that username for all subsequent accounts, you need to read what is in the dialog very closely, to ensure you have the right ones.

If that doesn’t work, delete the profile and create a new one, that usually solves the problem.

I had to set up a fleet of new laptops a couple of weeks back and each user had their own account, a sales account and an export account. It took a couple of restarts of Outlook, before it had all the passwords correctly associated. It is a pain, setting them up, but it all works very smoothly after that.

If Outlook loses its connection to the server, it can start asking for passwords again (timeout is somehow treated as a password failure), it has always done this. Closing Outlook and re-starting it is usually all that is required, it will reset the password failure and use the existing, saved password.

Not sure how this is relevant. There is a bug in the OS where ANY saved credential gets forgotten. It’s a known problem, in specific conditions, and after Tavis Ormandy poked MS with his details, MS is supposedly working on a fix.

Ah, okay. The problem with Outlook forgetting passwords is not necessarily related to this issue, it has always had problems, especially with multiple accounts.

I guess we have been lucky, we have upgraded over 200 PCs to 2004 and none are showing any of these problems.

right - this is not to downplay issues Outlook has by itself! But I am sure many people were going along just fine with their outlook setup until they got a major windows update. the bizarre part for me was that my AOL app passwords had to be refreshed each time, still scratching my head about that.

if you look at solution #2 from Tavis, certain 3rd party products may trigger it depending on how they set up background work. in my case it was my own ‘cron’ job I set up to run a cygwin shell. And easy enough to fix thanks to Mr. Tavis.