Mac OS X Server: How do I Relay outgoing mail to gmail using ssl on port 587?

madgunde · Feb 16th, 2008, 02:36 PM

I'd like to set up my mail server to Relay outgoing mail to gmail's smtp server, but gmail requires ssl and port 587 and on the Mail-->Settings-->General page, there doesn't seen to be any means of specifying what port to connect on and whether to use SSL or not.

I've tried entering the smtp.gmail.com host with the login and password for my gmail account and then enabling SSL for SMTP on the Advanced tab, but I suspect that is for clients connecting to my SMTP server, not for connection to the external relay.

I suspect this is supported by the postfix engine, just something that Apple hasn't put a GUI in to set.

I only use the mail server for sending email generated by my wordpress and phpbb websites hosted on the same server. I have to relay to an external SMTP server because Sympatico blocks me from using my own SMTP server for outgoing mail. I want to use Gmail because I'm not happy with the reliability of Sympatico's SMTP server.

I'm running Mac OS X Server 10.5.2 on a PowerMac G4 tower. I have a dynamic IP address and use dynamic DNS, although I don't think that matters in this case.

Any server admins who have done this? Thanks in advance.

John Clay · Feb 16th, 2008, 02:54 PM

I'm fairly sure that Gmail rejects outgoing messages sent to it's SMTP servers that are not from a Gmail address.

Your best bet for this is to switch to an ISP that doesn't block ports, and then to get a static IP and custom reverse DNS. I know of one ISP that offers this - TekSavvy. They have a $4/mo static IP plan, and will give you a custom reverse DNS (i.e., messages will be seen as originating from your domain, rather than xxxxx.teksavvy.com, or xxx.sympatico.ca, etc.). Many incoming mail servers will reject mail where the sender's SMTP server IP doesn't resolve to the IP.

I run my own mail server, but I relay everything through the TekSavvy SMTP server, as I can't be bothered to setup my own. This seems to work just fine.

madgunde · Feb 16th, 2008, 03:16 PM

Thanks for the recommendation John-Clay. Looks like TekSavvy charges about the same WITH a static IP as what I'm paying for Sympatico. Actually, it'll work out to $4 less per month, but I have to buy the modem.

How is their customer service and reliability? Had any outages and if so, how long? How's their Mac support and do you have any complaints/recommendations about their modems?

Thanks again.

John Clay · Feb 16th, 2008, 03:41 PM

	Quote:			Originally Posted by madgunde
	Thanks for the recommendation John-Clay. Looks like TekSavvy charges about the same WITH a static IP as what I'm paying for Sympatico. Actually, it'll work out to $4 less per month, but I have to buy the modem. How is their customer service and reliability? Had any outages and if so, how long? How's their Mac support and do you have any complaints/recommendations about their modems? Thanks again.

There are the occasional outages (for the non-emergency outages, they send an email to notify you of the downtime and the time bracket), while they upgrade their equipment, but the downtime is usually very short (hour or so), and in the wee hours of the morning.

Customer service is superb - the techs know what they are doing and it's all local (no outsourced crap). A few are Mac users as well. They also monitor the DSLReports.com forum, and provide support there (and other users pitch in as well). I've got the SpeedTouch 516 from them, as I couldn't be bothered to source it elsewhere. It can be had for around half the price they sell for, though. Keep in mind that you can use any extra Bell modems you have laying around, though the 516 will give you connection statistics (useful in debugging issues) and may yield a better connection (as it is a newer modem).

I'd say that 99% of the issues I've had with TekSavvy have been because Bell dropped the ball. Since I've been configured properly on Bell's end, I've had no problems (short of the hardware upgrades).

I currently have two accounts with them, once since August and one since November. The first one was the most painless, as it hadn't previously had DSL service. When migrating from Sympatico to another DSL ISP, Bell can be a bit careless. All the issues were quickly resolved, however. Also, keep in mind that you won't get any faster speeds than you get with Sympatico.

madgunde · Feb 16th, 2008, 03:50 PM

	Quote:			Originally Posted by John Clay
	I'd say that 99% of the issues I've had with TekSavvy have been because Bell dropped the ball. Since I've been configured properly on Bell's end, I've had no problems (short of the hardware upgrades).

That's what I've been afraid of, and the number one reason I'm still with Bell. It can be a hassle to get support when there is an issue just dealing with one company, I didn't relish having to deal with two companies that might point fingers at each other.

	Quote:			Originally Posted by John Clay
	I currently have two accounts with them, once since August and one since November. The first one was the most painless, as it hadn't previously had DSL service. When migrating from Sympatico to another DSL ISP, Bell can be a bit careless. All the issues were quickly resolved, however. Also, keep in mind that you won't get any faster speeds than you get with Sympatico.

As long as my speed doesn't drop, I'm OK with that. Also, is TekSavvy hostile towards bittorrent users? Do they throttle traffic for P2P traffice to your knowledge?

John Clay · Feb 16th, 2008, 03:59 PM

	Quote:			Originally Posted by madgunde
	That's what I've been afraid of, and the number one reason I'm still with Bell. It can be a hassle to get support when there is an issue just dealing with one company, I didn't relish having to deal with two companies that might point fingers at each other. As long as my speed doesn't drop, I'm OK with that. Also, is TekSavvy hostile towards bittorrent users? Do they throttle traffic for P2P traffice to your knowledge?

I agree with your first point, and that's what kept me with Sympatico for so long. However, the monetary savings of TekSavvy, combined with the sanity savings, brought me over. TekSavvy will lean on Bell for any problems, and you don't have to deal with them at all.

Speeds shouldn't drop, as long as you're connected to the same CO or remote DSLAM.

TekSavvy has been very open on the last issue, and have stated that they have not, and will not, block, filter or throttle any connections. They prefer, as evidenced by recent hardware upgrades, to upgrade infrastructure rather than restrict users. As a note: they have discussed blocking port 25 for all users, due to spamming and other issues caused by viruses, but this would be a free of charge opt-out policy.

madgunde · Feb 16th, 2008, 04:10 PM

	Quote:			Originally Posted by John Clay
	I agree with your first point, and that's what kept me with Sympatico for so long. However, the monetary savings of TekSavvy, combined with the sanity savings, brought me over. TekSavvy will lean on Bell for any problems, and you don't have to deal with them at all. Speeds shouldn't drop, as long as you're connected to the same CO or remote DSLAM. TekSavvy has been very open on the last issue, and have stated that they have not, and will not, block, filter or throttle any connections. They prefer, as evidenced by recent hardware upgrades, to upgrade infrastructure rather than restrict users. As a note: they have discussed blocking port 25 for all users, due to spamming and other issues caused by viruses, but this would be a free of charge opt-out policy.

Excellent. Thanks for the information John Clay. Having a static IP has always been a wish of mine and would make my life hosting my own blog/forum/email so much easier. I'm only a hobbyist, but I really love the autonomy of having total control over my own hosting rather than relying on third parties. Since it's more for personal use, I'm not worried about possible downtime that is a risk when hosting your own server on a non-redundant consumer DSL line. That being said, I'll probably continue to use GMail for my personal domain email rather than running my own IMAP server for reliability reasons.