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Outlook 2010 POP Authenication fails with knows good credentials

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  • Outlook 2010 POP Authenication fails with knows good credentials

    I've been presented with a strange issue on a small group of PC's (3x windows 7 +office 2010 and 1x XP with office 2003) Server 2008 domain members
    On friday email was working normally
    come Monday morning outlook fails to authenticate to a POP3 account hosted outside of this network on all 4 PC's
    the same account settings allow another computer not associated with the domain (my laptop, other staff laptops) to use the pop 3 account normally
    outlok will connect to another pop3 account ok (my gmail)
    No updates have been installed over the weekend
    I've repaired outlook - no joy
    removed and reinstalled outlook rebooting inbetween -no joy
    same sympton on local admin user account on the PC's - chkdsk run, didn't seem to defect issues
    temporory files removed
    error in outlook is that the server rejected the username or password, so the server can be contacted (pings successfully)
    as new accounts have been created I've carefully been through the settings to make sure the authentication methods are correct (as default no SSL etc)
    I've not yet installed 3rd party mail app like thunderbird - going to try this next to confirm I seem to have pinned the issue down to outlook 2010 and 2003 on one email account only. It really sounds like a possible provider issue but the accounts work fine on other machines, so that kinda throws it off a but
    any ideas?
    if there a cache for outlook authentication? how can I enable some advanced logging in outlook.I'm tempted to use a packet sniffer to see if the password is being sent correctly
    I really have looked at this carefully.made sure no stupid typos etc.
    I've disjoined the machine from the domain. created a new user - same symptoms
    I've run wireshark packet sniffer to verify the password is being sent ok. seems to be, confirms server returns bad password error but password is definately 100% correct as outlook express on another machine can use the pop account ok
    I've even had the passoword changed by the provider just to try something different
    windows live mail on the same windows 7 machine (only testing on one initilly) also fails to authenticate. I guess it uses the same framework maybe?
    I really could do without formatting 4 PC's and fixing all the 3rd party software that needs updates etc to work, as they are production machines
    any help apreciated
    Last edited by The Phesant Has No Agenda; 18th April 2011, 15:14. Reason: Update, furhter checks made

  • #2
    Re: Outlook 2010 POP Authenication fails with knows good credentials

    Have you tried manually authenticating with the remote server via telnet?
    Often helps troubleshoot the problem.

    Disable anti virus!

    telnet some.server.fqdn 110

    You should get a POP3 ready kind of response

    USER someusername

    you should get an OK kind of response

    PASS somepass

    you should get an OK kind of response

    If this does not work, where does it fail and with what error?


    • #3
      Re: Outlook 2010 POP Authenication fails with knows good credentials

      Antivirus is the first place to look as David! said - if you have one of those that filters network traffic. Also any software firewalls for the same reason.

      We had an issue with POP traffic once where a Cisco SOHO router would corrupt the traffic stream. That wasn't at the authentication stage though it would hang the connection immediately after a RETR.

      Actually we had it happen a couple of times with different SOHOs but only with one ISP (BT Internet).

      Can you get one of the machines onto a different network/Internet connection? That'll help you pin down whether it is the machine or the network causing your issue.