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I just set up my server today with one of my new static IP addresses to act as a mail and web server. The web server is working fine, and the mail server is working fine to receive mail, but I am unable to send any mail except to my own domain. I've looked in the SMTP log and it is filled with entries like this:

Oct  3 21:36:02 osxserver postfix/smtp[17767]: connect to mx3.hotmail.com[65.55.92.136]: Operation timed out (port 25)
Oct  3 21:36:13 osxserver postfix/smtp[17965]: connect to mx1.icloud.com.akadns.net[17.172.34.10]: Operation timed out (port 25)
Oct  3 21:36:32 osxserver postfix/smtp[17767]: connect to mx1.hotmail.com[65.55.37.72]: Operation timed out (port 25)
Oct  3 21:36:43 osxserver postfix/smtp[17965]: connect to mx3.icloud.com.akadns.net[17.172.34.64]: Operation timed out (port 25)
Oct  3 21:37:02 osxserver postfix/smtp[17767]: connect to mx3.hotmail.com[65.55.92.168]: Operation timed out (port 25)
Oct  3 21:37:13 osxserver postfix/smtp[17965]: connect to mx3.icloud.com.akadns.net[17.172.34.65]: Operation timed out (port 25)
Oct  3 21:37:32 osxserver postfix/smtp[17767]: connect to mx1.hotmail.com[65.54.188.72]: Operation timed out (port 25)
Oct  3 21:37:43 osxserver postfix/smtp[17965]: connect to mx4.icloud.com.akadns.net[17.172.34.66]: Operation timed out (port 25)
Oct  3 21:38:02 osxserver postfix/smtp[17767]: connect to mx3.hotmail.com[65.55.92.184]: Operation timed out (port 25)
Oct  3 21:38:13 osxserver postfix/smtp[17965]: connect to mx6.icloud.com.akadns.net[17.172.34.70]: Operation timed out (port 25)
Oct  3 21:38:32 osxserver postfix/smtp[17767]: connect to mx4.hotmail.com[65.55.92.184]: Operation timed out (port 25)
Oct  3 21:38:43 osxserver postfix/smtp[17965]: connect to mx2.icloud.com.akadns.net[17.172.34.12]: Operation timed out (port 25)
Oct  3 21:39:02 osxserver postfix/smtp[17767]: connect to mx2.hotmail.com[65.54.188.126]: Operation timed out (port 25)
Oct  3 21:39:13 osxserver postfix/smtp[17965]: connect to mx2.icloud.com.akadns.net[17.172.34.11]: Operation timed out (port 25)
Oct  3 21:39:32 osxserver postfix/smtp[17767]: connect to mx4.hotmail.com[65.54.188.126]: Operation timed out (port 25)
Oct  3 21:39:43 osxserver postfix/smtp[17965]: connect to mx1.icloud.com.akadns.net[17.172.34.9]: Operation timed out (port 25)
Oct  3 21:40:02 osxserver postfix/smtp[17767]: connect to mx4.hotmail.com[65.55.92.168]: Operation timed out (port 25)
Oct  3 21:40:13 osxserver postfix/smtp[17965]: connect to mx5.icloud.com.akadns.net[17.172.34.68]: Operation timed out (port 25)
Oct  3 21:40:13 osxserver postfix/smtp[17965]: 449966C1EC: to=<jehamlett@icloud.com>, relay=none, delay=39809, status=deferred (connect to mx5.icloud.com.akadns.net[17.172.34.68]: Operation timed out)

Any recommendations on how I can fix this so that I can send mail? My server is running OS X Server 10.4.11 and my ISP is AT&T u-verse business class.

Wesley
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user192603
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1 Answers1

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Regardless of your ISP being business class, often times outbound port 25 is blocked by default on all accounts and you need to explicitly enable the ability to make connections over port 25 either in some kind of ISP control panel or make a call to your account executive.

To troubleshoot, open telnet and attempt to connect over port 25 to one of the servers listed in gmail or hotmail's MX records, for example. You will most likely not be able to connect. Once you have that port opened by your ISP, voilà!

Wesley
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    That was it! Port 25 was blocked for all IPv4 traffic. I was able to call and get it unblocked. (Interestingly enough, it was not blocked to IPv6 traffic. Telnet was able to connect when I tried the google servers.) – user192603 Oct 04 '13 at 19:48