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We are experiencing a problem after migrating to a new mail server where users that connect to the mail server through Outlook (using IMAP) get prompted periodically/frequently for their username and password.

Pop-up prompts "Enter your username and password for the following server" and contains the name of the server, username and password. Since most users have opted for Outlook to save their passwords, they simply have to click on "Ok" to log in successfully and continue, but after a few minutes they will be prompted yet again. This probably happens when Outlook tries to connect to server periodically to send/receive mail.

We are running Windows 2008 Server using MailEnable Enterprise version 6.53. The server is hosted on AWS Amazon Web Services. Users do not connect via a domain, but use simple IMAP with servername, username and password to connect. It is not a connectivity issue because these same users used to connect to the old server without this problem.

What could be causing this and how do I fix it? (I did see Outlook 2003 repeatedly prompts for username and password but that relates to users logging on to a domain...)

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Does the problem occur with someone using a fresh Outlook profile? –  Simon Catlin Aug 22 '12 at 20:01
    
I assume that by "fresh" you mean deleting existing settings and setting it up as a new profile? We haven't tried that yet - I can try it on one of our users and see if that helps...Didn't really want to go this route since our 2000+ users all access their mail from remote sites where we can't really help them with a new Outlook setup and we'd have to guide them remotely. I assumed it had something to do with new server since outlook worked on the old server. –  Stanley Aug 23 '12 at 8:09

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