(using OS X mail) I have a vps, and on two separate domains, I set up an email on each, using mail.thedomain.com . One of them works perfectly. But when I add the second smtp setting in mail, it fails.

In OS X mail, it will only allow one smtp on the same server. Anyone know of this issue? It occurs on another server as well.

What do you mean, only allow one SMTP on the same server? The way you've phrased it, at least, it doesn't make any sense. Mail.app can send multiple email accounts through a single SMTP server, or multiple servers.

I would have thought so too, but no, it simply won't.

If the smtp is on another server, no problem. But 2 or more smtp from the same physical box,. mail won't do it. Only the first entry works. I've tested and retested the hell out of this, and can't figure out why this would be.

What you're saying again doesn't make sense.

Explain your complete setup (server side as well). Mail can, absolutely, send mail from multiple email addresses to the same SMTP server.

Are you trying to run 2 SMTP servers on the same IP address? You're not providing enough detail.

yes. two different smtp references on the same server, same IP address. -different domains-.

each smtp is referred to as mail.thedomain.com, they are different domains, on the same, physical server. The VPS uses whm, and cpanel for each account.

If I set up an email at one domain, and set the smtp to it's mail.ITSdomain.com, and then set up another domain, with an email with it's smtp set to -that- domain... mail.THATdomain.com, the outgoingserver fails for the second entry. only the first one works.

the setup, is simple, basic VPS for multiple domains.

Does it fail with an error or any sort of reference?

it simply says it can't find it. sets to offline. It hangs for ever trying to send it. Though I can use either one as long as the other smtp reference doesn't exist in the outgoing list at all. Telnet also works fine to either.

I just never noticed that you cannot use different smtp references to the same physical server in mail. Odd.

I imagine I could, use the reference to the primary domain for the VPS.

update, set them up in thunderbird mail, they both work. No go in mail, checked and rechecked settings. A bug in mail of sorts?

definitely a bug in mail.

I can set them up in thunderbird, but no way in mail. This is driving me insane.

definitely a bug in mail.

I can set them up in thunderbird, but no way in mail. This is driving me insane.

Very strange, and I suspect a fringe case as well. I'd submit it to Apple as a bug that needs fixing.

I have a tendency, to be the fringe case it seems.

so it isn't just mail.

I have to turn on ssl for outgoing server in order for this to work. You shouldn't have to correct? Generally ssl is when you use the host domain (and it's certificate if it has one) correct?

Do you have SSL certs setup for each domain? I'm pretty sure that SSL certs are restricted to the domain they're built for. Sounds like your primary one works fine using the built-in self-signed cert but the add-on domains aren't happy with it.

Just a guess.

I have a tendency, to be the fringe case it seems.

I'm with ya on that one. I find "issues" with everything, software, hardware, whatever.

Do you have SSL certs setup for each domain? I'm pretty sure that SSL certs are restricted to the domain they're built for. Sounds like your primary one works fine using the built-in self-signed cert but the add-on domains aren't happy with it.

Just a guess.

no, I don't. I don't have any need for ssl on these domains yet. I'm not sure what happened, but there was some back and forthing with the techs, and somehow, while they didn't say there was a problem, it magically started working.

Oddly the other server I have, worked fine with the usual settings. I think I may be moving my stuff into a dedicated box at the other company in the new year anyway.

But when you turn on SSL for the outgoing SMTP it needs some sort of cert in place for it.

Anyway glad it seems to be working for you.

yeah I know, but it wouldn't work at all without ssl initially which is odd, I simply got a message saying it couldn't identify the server blah blah that you'd usually get, and bang it's send.

Now, it can send without ssl, magically.

Yep sounds like they found the "problem" (or in their terms no problem) and got it sorted for you. I hate when they do crap like that, why not just be honest and say "Yep, we found the issue."