Erik,
  Is the issue that you check the check box to retain password, and then 
later it is clear?
-or-
  Is the issue that you check the check box to retain password, and the box 
remains checked but Outlook won't send the password and it prompts you for 
it?

In the last two weeks I have run into 2 similar things to this (no solutions 
yet)

1) Outlook EXPRESS - the check box stays checked but prompts for password 
exen though the password is entered correctly in the Server Tab. Only one 
account involed here.

2) Outlook EXPRES - the check box stays checked but the login fails. Click 
send receive right away and it works the second time.  This occurs on the 
second account connecting to the same POP3 server.

hope this helps jog something for someone,
Zack

>Has anyone had any experience with this problem? It seems to exist
>whenever you create a second email account profile in Outlook 2002 and
>that account checks for mail on the same POP3 server as your first
>account. (We are checking email addresses from different domains hosted on
>the same POP3 server.)
>
>Microsoft has a KB article on it (Q290684), but the instructions don't
>make sense under W2K Pro. Any help would be greatly appreciated!
>
>List Charter and FAQ at:
>http://www.sunbelt-software.com/exchange_list_charter.htm
>




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