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I cannot seem to get the SMTP proxy to work reliably with my Outlook users. The functionality is there but fails frequently. I have a number of people using Thunderbird and seldom hear a peep from them. Occasionally they will say they can't send mail but I think it is usually due to switching networks (hotel to client site) while on the road....a reboot usually fixes it.
My Outlook 2003 users ALL have issues. Usually it will just timeout and leave their messages as unsent. I 'think' it has something to do with the Hotel network's security settings but can't seem to narrow it down.
Originally I had issues with port 25. It seemed as though some hotels would block SSL on port 25 so I setup a NAT rule on a different port that accepted the connection and forwarded it on. This worked great for Thunderbird users but Outlook still had issues.
I've looked through the logs which hasn't been that helpful because when the Outlook users have a timeout issue, nothing is logged. I did however find the following under a number of entries from Outlook users:
SMTP protocol violation: synchronization error (input sent without waiting for greeting): rejected connection from H=hostname+IP_Address
When this happens the message is still delivered....
1. Has anybody had issues with Outlook users sending mail while on the road?
2. Could it be that Thunderbird has a 'Use TLS' option and Outlook only has 'Use SSL?'
Any help will be greatly appreciated!!!
My setup is as follows:
SMTP Proxy = Enabled
Allows relay from Internal network
Use RBLs, Deny RCPT Hacks, Verify recipient, Verify sender enabled.
Scan outgoing messages with content filter = off
Spam protection enabled
SMTP Authentication = Enabled
Require TLS = Enabled
Authentication Methods = LDAP
Regards,
Claud1e
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