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I configured Outlook to use port 25 on my ISP's smtp server. That works fine and I can send email. But if I try to use the server in one of my applications (using JavaMail), I can't connect to the server. Same thing if I try to "manually" telnet to it: I get

telnet: Unable to connect to remote host: Connection refused

How is this possible? And how do I configure my application to be able to send mail?

Edit to add more information:

Wireshark shows that when Outlook tries to send email, it connects to port 25 of the ISP's smtp server. Everything works as expected. When I try 'telnet server 25', the connection never makes it to the server. I see 'Destination unreachable (Communication administratively filtered)', which seems to indicate the firewall at my workplace blocked it. If that's the case, how does the firewall know to let Outlook through?

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Are you sure you didn't configure SSL/TLS in Outlook for SMTP? –  thims Dec 22 '11 at 17:42
    
Exactly how did you setup mail in Outlook to your ISP? If it's POP3, then the connection to the server is on port 110 (POP3), not 25 (SMTP). –  Ƭᴇcʜιᴇ007 Dec 22 '11 at 18:42
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@techie007, you cannot send mail over POP3. It's always SMTP. –  grawity Dec 22 '11 at 19:21
    
@grawity Yeah ME = brainfart, it's 110 to get it, but it sends on 25. Sorry about that. ;) I was thinking about POP3 'listening' on 110. I'd still like to know how the account is setup in the OP's Outlook. :) –  Ƭᴇcʜιᴇ007 Dec 22 '11 at 19:30
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Any anti-virus/"Internet Protection" suites installed/enabled? They may block non-email clients (or unknown email clients) from sending from your computer in case you unwittingly become a spam-zombie. –  Ƭᴇcʜιᴇ007 Dec 22 '11 at 19:37

3 Answers 3

I would use a network sniffer like Wireshark (free) to see what Outlook does - Wireshark's "Follow TCP Stream" is useful for this.

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Microsoft has a free Network Monitor. –  thims Dec 22 '11 at 17:43

Bear in mind that Windows can block outbound connections on a per-application basis. Check the Windows Security control panel.

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up vote 2 down vote accepted

techie007 was on the right track. The anti-virus running on the computer is what was blocking the connection. I'm now running the program from a linux box and that works fine.

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