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Cannot send POP3 email from Outlook 2003 except off site

Posted on 2009-05-13
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Last Modified: 2013-11-30
Environment:  Windows 2003 SBS, all current patches and updates.  Exchange is used for internal mail only, and POP3 used for external mail.  Connection is via a somewhat slow wireless ISP.

Outlook 2003 on multiple client computers, using POP3 to send/receive email to hosted email domain.  Can receive mail fine, but outgoing mail fails.   When testing email (within Outlook email accounts), two errors appear:

Send test e-mail message: The specified server was found, but there was no response from the server. Please verify that the port and SSL information is correct.

Find outgoing mail server (SMTP): Outlook could not connect to the outgoing mail server (SMTP).  The problem could be the server name or port, or your server may not support SSL.  Verify your port and SSL settings..."

This issue is the same for all computers at the site.  The same email server is used for incoming POP3 and outgoing SMTP traffic.  Webmail works from this site.

Off-site, we are able to send/receive mail without any problems.  AVG AntiVirus on the server and on the client PCs is set to check incoming mail only, not outgoing mail.

No changes have been made to any firewall settings, yet outgoing mail is blocked.  The Outlook client can find the SMTP server, but does not receive any response.  Any ideas?
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Question by:4RunnerBob
9 Comments
 
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Expert Comment

by:MiniDevo
ID: 24373676
Have you tried authenticating the outgoing mail with smtpauth.domain.net? It will prompt you for the username and password, you can either set it to the incoming credentials, or manually set it. The only reason I recommend it is because there may be an issue with tunneling, etc. and re-authenticating may bypass this.
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Expert Comment

by:Dave Howe
ID: 24374530
do you have an antivirus solution? seen issues where smtp outbound was blocked by antivirus.
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Author Comment

by:4RunnerBob
ID: 24374905
AVG Antivirus 8.5 on server and PCs, all configured to check incoming email only.

PCs connect to the Internet through the Windows 2003 SBS server.  Server has two network connections, one to LAN and another to the Internet connection.  No firewall or other configuration changes have been made for many months.

Could a recent patch or update cause this problem?
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Expert Comment

by:Mestha
ID: 24374922
Name resolution?
Inside, does the name for the outbound server resolve correctly?

Simon.
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Author Comment

by:4RunnerBob
ID: 24374937
Name resolution works.  The same server name is used for incoming (POP3) and outgoing (SMTP) mail, and incoming mail is working fine.  We are also able to ping the server from the PC as well.
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Accepted Solution

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dcsdave earned 500 total points
ID: 24375139
I have seen a few ISPs block emails that aren't sent through one of their own connections.  A work around that I found was to call the current ISP and ask them for a server to send through.

Example:

myemail@myemaildomain.com won't send through mail.myemaildomain.com SMTP on the office network.

Call your current ISP for the office and ask them for an SMTP setting that you can send your mail through.

myemail@myemaildomain.com can send through mail.myisp.com SMTP on the office network.

In all the networks that I manage I went away from POP other that bringing it into the exchange server via GFI and then just using exchange to send and receive.  This relieved a lot of headaches when troubleshooting email issues.

Hope that helps.
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Author Comment

by:4RunnerBob
ID: 24393854
The ISP (DTN Speed Net) states that they do not block any ports or outbound email traffic.
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Author Comment

by:4RunnerBob
ID: 24396157
If no configuration changes have been made to the server, is it possible that we need to check any settings?  The server uses one network connection to connect to the DTN Speed Net wireless ISP, and another network connection to connect to the LAN, and other computers on the internal network.

The email host does not see any (outbound email) smtp traffic hitting their server, yet the same server show normal POP3 traffic as the PCs download their incoming messages.  What can block outgoing smtp email, when the standard ports are used?
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Author Closing Comment

by:4RunnerBob
ID: 31580910
Although we called and asked DTN Speed Net three times if they were blocking any outbound email, they said no each time.  We fixed the problem by trying different possible smtp servers, and using smtp.dtnspeed.net worked.  No help from DTN Speed Net, which should have provided this simple information during the first phone call.  They later said that they "don't block outgoing email in any way, you just have to send it through our smtp server", for what is worth.

Thanks, DCSDave for pointing us in the right direction.  Next time, in addition to asking the ISP if the block smtp outgoing mail, we will also ask if they have a required smtp server.
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