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TC10284

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A roadwarrior that uses Apple Mail and iCal is having issues. He travels around the country and the world a lot. He tells me that in different hotels/places to get his email to work he has to change his Apple Mail account SMTP server port from the default of 25 to the alternate port I have setup of 2525. Then things start working. This doesn't happen all the time, just sometimes.
I have pfSense as the router/firewall between the server and the Internet.

Here are the ports I have forwarded (with applicable firewall rules)
(SMTP) 25 - TCP
(SMTP Alt)2525 - TCP
(POP3) 110 - TCP
(IMAP) 143 - TCP

We are not using SMTP-S and POP3-S yet because we still only have a self-signed SSL cert.

As for iCal, it is setup to use the Kerio calendar (same one that is in webmail). It works when he is "stationary", but when he travels it does not. He has two accounts under iCal. They both say the same. The error is:

"The request for account "email<_at_>company.com" failed.

The server responded with
"HTTP/1.1 504 Proxy Timeout ( Connection timed out. For more information about this event, see ISA Server Help. )"
to operation CalDAVAccountRefreshQueueableOperation.

It seems like this happens when he travels and taks his Macbook with him. I have an account setup in Outlook 2007 on a Windows 7 machine and do not have any issues with connecting to the mail server or sending email. I don't connect to the Kerio calendar in Outlook though.

Any ideas?
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stewie

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If he's using public networks then port 25 is probably closed on the public network. This is increasingly common as spammers use these networks to send their garbage so either the company or the ISP closes port 25. (And if he is using a public network it's extremely easy steal his credentials, extremely easy!) So just use web mail.

As for iCal, when you say "stationary" do mean at home, at the office, both??? Does web mail work when he gets these errors? ISA server...so is he setup to use a proxy??? Again, if this not your network it's hard to say what's going on. Best bet on the road, use web mail. Ports 80 (http) & 443 (https) are almost always open & unencumbered.
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TC10284

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I see. Perhaps using SMTP-S and POP3-S would help and also help secure login credentials? I do agree with using webmail. Preferably https.

By "stationary", I mean at the office and at home. It seems to work in those locations from what I know.

He should not be configured to use a proxy. Not sure where/why that's coming up.
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stewie

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Might help with both issues. Or use VPN & definitely solve both problems.

I suspect the proxy message was due to the DHCP settings on the network he was using. Bottom line, if he's able to connect from home directly through the Internet then everything is most likely set up & working properly. But if he can't connect from a foreign network it's probably because of the way the foreign network is setup & there's not much you can do about that. If it's a frequent enough issue, get a data plan from a mobile provider or just use a smartphone.

Good luck!
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