Outlook login/windows security pops up every time

Every time I start Outlook 2010 , it pops up this dialog:

How to get rid of this dialog ? - "Remember my credentials" is checked, but it doesn't ... remember.

This worked for me. Basically delete all the wrong credentials in your vault and save the correct ones in. Here's how:

1. Click Start, click Control Panel, and then click Credential Manager.

2. Locate the set of credentials that has Outlook in the name.

3. Click the name to expand the set of credentials, and then click Remove from Vault.

4. Repeat step 3 for any additional sets of credentials that have the word Outlook in the name.

Then it should ask you for your credentials again. But this time make sure you have them right and click "remember me".

This could be an issue with Outlook not authenticating properly against your exchange server. I have seen this issue when users upgraded to Office 2010. One thing you could try doing is repairing the email account. To do this, go to Start > Control Panel > then search Mail > Email Accounts. Highlight your email account and click "repair". Once this is done, restart the machine and see if this issue continues. If you do not have access to your exchange server, I recommend contacting your system administrator. This should be a simple fix. Good luck!

There are two possible solutions available from Microsoft, here:

  I get an Enter Network Password prompt
  http://office.microsoft.com/en-us/outlook-help/i-get-an-enter-network-password-prompt-HA010151354.aspx

What you're seeing is a prompt for your network password. It probably is related to the second solution that explains how to clear out the Protected Storage System Provider sub-key in the Windows Registry. Unfortunately this is not a new problem and I remember having to fix it many times with MS-Office 2003 on Windows XP when MS-Exchange was a part of the picture too.