I use Outlook at work and at times it repeatedly asks for Username/Password and fails to connect to the server and receive or send emails (even though I have checked the small ‘Remember Me’ box). I noticed that this usually happens after I have changed the password (mandatory in our organization, every 3 months). A tech-support staff once ended up spending hours trying to fix the issues, without success. I later figured that the solution is rather simple but perhaps not very well known:
There are two things you could do to fix the issue:
1) When you enter your Username/Password in Outlook and click on the ‘Remember Me’ button, it saves the credentials on your local system and retrieves it automatically whenever you start Outlook thereafter.
When the Password is changed however, Outlook can at times continue to retrieve the old saved Password (without you realizing it – since all you see in the Password box are dots). Since it finds a mismatch in the new and old passwords, it fails to connect to the server and keeps prompting you to supply the (new) Password – which, obviously, can be quite annoying.
What you would need to do is to go to the Control Panel-> User Accounts-> Manage your Credentials and once there remove all ‘Generic Credentials’ associated with Outlook.
Now, once you re-start Outlook, it should prompt you for the new Password and that should work. In case, it doesn’t move to Step 2.
2) Go to ‘File’ in outlook (Left most tab on top) -> Account Settings -> Account Settings -> Now highlight the Email you want to fix -> Click on Change -> More Settings -> Connection -> Un-check the box “Connect to Microsoft Exchange using HTTP”
Save the changes and restart Outlook. It should connect to the server now.
Did the above Steps help you resolve the issue? Do you know of any other tips that can be useful to fix this problem? Do share your comments below.