This is a direct challenge to anyone out there that believes they know Outlook well Basically we recently installed a new server on a domain (Zentyal Linux Community Edition). As far as taking the machines off the old failing server and onto the new Linux machine running Samba 4 as a PDC that was moderately flawless. The issues arose when we created new profiles on the workstations. Basically they had an existing install of Office 2013 (Standard Edition, Charity License x64) and after the new profile was created for that machine everything seemed fine, Word opened fine and opened documents as did Excel. We setup Outlook and re-entered all the POP3 settings into it and did a Test Account Settings.... (*sigh*) it waited a moment and failed with an -ERR[AUTH] error. I turned on advanced logging in Outlook and it got to the PASS [tx] part and failed. After much troubleshoot I tried a telnet client on Port 110 and sent a (edited for obvious reasons)


CAPA
USER username@domain.com
PASS realpassword

This worked fine, we tried again and again in Outlook with no luck it kept prompting for the user/password regardless of what we entered, in fact we even tried another mail providers/mail account with no luck. Next I tried a small open source mail program it worked fine! I grew annoyed beyond believe I installed Wireshark and did a capture. Sure enough in Telnet and the small open source program I could see it send plaintext the username and password. When I did a packet capture of Outlook and it's interaction with the mail server and CLEARLY it seemed to be sending a null password every single time no matter what was typed.

Does anyone out there have any idea what I could do to further troubleshoot this issue?