problems with outlook 2003 and secure pop3

  • From: "Harondel J. Sibble" <exchangelist@xxxxxxxxx>
  • To: "[ExchangeList]" <exchangelist@xxxxxxxxxxxxx>
  • Date: Mon, 19 Dec 2005 14:17:59 -0800

Bit of an odd one, have several users backeast connecting to our Exchange 
server. It has secure pop3 on port 995 and secure smtp on port 465, it works 
find for sending, and using my account on the exchange server, downloads of 
email work without issue. on their accounts I see the same problems they are 

The 2 users back east have XP Pro machines and Outlook 2003, upgraded from 
Outlook 2000, office 2000 is still installed, only the outlook portion was 
upgraded to 2003.  They are running the Trend Antivirus client from CSM4SMB 

The Exchange server is Exchange 2003 Enterprise with SP2 running behind a 
Fortigate FG60 firewall on a 1.5mb dsl connection.

On my test machine here, it's running Windows 2000, Outlook 2003 and the 
Fortigate Forticlient (antivirus, firewall, vpn etc). When I pop email from 
my account, there are no issues, when they pop email, it times out after a 
few minutes. Sometimes it will download no messages, other times it will 
download say 3 of 6 messages and hang on the 4th one.  When Outlook 
reconnects, they end up with duplicats, triplicates on the new messages. In 
the test I had one of the users do a few minutes ago, she ended up with 8 
copies of some of the messages.

On my machine, logging into one of the users's accounts resulted in 3 or 4 
copies of some messages.

For the first user back east, everything was working fine until about a week 
ago, he'd been successfully sending and receiving email without issue. His 
notes follow. This user had 955 messages in his inbox, but moving them to 
another folder and putting in say 2 or 3 messages in the inbox results in the 
same problems.

The only thing I can think that was changed around that time was that our IP 
address got on a SpamHaus blocklist (not our fault) as our ISP had been 
ignoring a prior SpamHaus block for the past year and it got escalated 
resulting in the entire class c we are in being blocked.  Other than that, 
there have been no major changes to the server corresponding with the 
problems. Being that the ISP ignored the blockage, I've since got an ip from 
a non blocked class c and put the server on that and adjusted the DNS 
accordingly and mail is flowing, however the problem with pop3s is still 
happening :-(

Harondel J. Sibble 
Sibble Computer Consulting
Creating solutions for the small business and home computer user.
help@xxxxxxxxx (use pgp keyid 0x3AD5C11D)
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