Cellular Phone Forum / Providers / ATT Wireless / August 2008
iPhone "can't send mail...invalid e-mail address"
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David G. Imber - 24 Aug 2008 04:33 GMT I inquired here a short while back about a persistent problem I've been having with the iPhone. It fails to send mail sometimes and feeds back a message saying that a recipient e-mail address is invalid, when I know that it's not (and of course the error message doesn't say which address is "invalid").
For the time being, I seem to have found a solution, and improved my mail transmission as well.
As iPhone users know, they pre-configure the AT&T SMTP server in a fallback position, so that it's used if the main doesn't work. But clearly their data network (such as it is) "likes" their own SMTP server.
When I reversed the positions and put _their_ SMTP first and my own network's in the fallback, mail started going through smoothly.
For now, that's my solution. It galls me a little because my own network server should properly be my main server, and their network should handle this without making me work so hard, but there you have it. DGI
Anybody - 24 Aug 2008 05:07 GMT > I inquired here a short while back about a persistent problem > I've been having with the iPhone. It fails to send mail sometimes and [quoted text clipped - 19 lines] > > DGI Many email SMTP servers do not like being accessed directly via another network connection (that's why you usually have to use a webmail inferface instead when acessing email from someone else's Internet connection). If you are using AT&T's iPhone network to connect to the Internet then your own network's SMTP server may well complain. This is done on purpose to prevent spammers simply using any old SMTP server.
By changing AT&T to be first probably means all out-going emails are being sent using AT&T's server instead of your own complaining one ... that's the way it's meant to work. You should probably delete your own SMTP server completely from the iPhone.
David G. Imber - 24 Aug 2008 07:52 GMT On Sun, 24 Aug 2008 16:08:10 +1200, Anybody
>Many email SMTP servers do not like being accessed directly via another >network connection True, but I work closely with my sys admin, and he says there should be nothing preventing me from accessing it. On the other hand, he's decidedly NOT a fan of AT&T's data network, and suggests that the hang up is almost certainly their failure or quirk or what have you.
>You should probably delete your own >SMTP server completely from the iPhone. I don't think that should be necessary. For one thing, my own SMTP server has worked in the past, so it's clearly feasible (just giving more credence to my sys admin's well-qualified opinion that AT&T's data network just blows). And if their own server is in the first position and mine is in the fallback, and theirs fails, I may as well put my own in, because it's better to have some chance of mail going out than none. It certainly can't hurt, being in the secondary rather than primary order in the queue.
Thanks for your advice! DGI
Anybody - 24 Aug 2008 08:27 GMT > On Sun, 24 Aug 2008 16:08:10 +1200, Anybody > [quoted text clipped - 5 lines] > he's decidedly NOT a fan of AT&T's data network, and suggests that the > hang up is almost certainly their failure or quirk or what have you. Maybe, maybe not. I obviously don't know your person and you may have one of the very few good ones, but in my many years of experience most tech people will tell you the fault is not with their system, usually because they're either simply too damn lazy to actually look and/or are so high-and-mighty that there can't possibly be a problem with what they're doing, and in the case of a Mac user problem they simply know nothing about Macs and don't want to know.
It took me about two weeks (and MANY phonecalls) to get my ISP to even look at fixing a problem that was stopping Mac OS 9 dial-up users from logging in. The (no)help desk getting insisting that there was no problem, the tech people kept insisting there was no problem, and they both kept telling me the problem was at my end and wanting to check my settings ... despite me telling them over and over that it had happened before and defintely was at their end. :-(
> >You should probably delete your own > >SMTP server completely from the iPhone. [quoted text clipped - 7 lines] > going out than none. It certainly can't hurt, being in the secondary > rather than primary order in the queue. One company I work for has had similar problems from their wired computer network. Sometimes it would send and other times it wouldn't, but in the end it did turn out to be this "you're not on the right network to use this SMTP server" problem.
Sometimes the server authentication / password settings is meant to be used, but mail can still sometimes get through in some peculiar quirk. In fact I know of one iMac on a network of Macs that always returns a "mail could not be sent" message for every outgoing email, even though the message has actually been sent and recieved at the other end.
Of course, another possibility for you is perhaps a weak signal on the iPhone causing problems. Or as your tech person suggests, and AT&T problem communicating your own server.
David G. Imber - 24 Aug 2008 20:31 GMT >Of course, another possibility for you is perhaps a weak signal on the >iPhone causing problems. That is very possible, I think, because I'm stubbornly keeping 3G turned on, even though here in the heart of Manhattan 3G is very poorly implemented and spotty.
My sys admin's a pretty good guy, and I trust him, though I'm not qualified to judge his expertise. He does know Macs though, and uses one that's running VMware Fusion in his array.
Thanks! DGI
DevilsPGD - 24 Aug 2008 10:51 GMT >On Sun, 24 Aug 2008 16:08:10 +1200, Anybody > [quoted text clipped - 5 lines] >he's decidedly NOT a fan of AT&T's data network, and suggests that the >hang up is almost certainly their failure or quirk or what have you. Have you tried an alternate port? If your sysadmin isn't stuck in the 80s and 90s, port 587 might work, whereas if AT&T is being even half way responsible with their network, they'll have off-network port-25 access blocked.
David G. Imber - 24 Aug 2008 20:34 GMT >Have you tried an alternate port? If your sysadmin isn't stuck in the >80s and 90s, port 587 might work, whereas if AT&T is being even half way >responsible with their network, they'll have off-network port-25 access >blocked. On sys admin's advice I'm using port 587. Using AT&T's SMTP as my main, mail is definitely going through, although it takes _forever_ to send, which I don't understand.
Thanks for your advice, DGI
Matt Simpson - 25 Aug 2008 14:39 GMT > Have you tried an alternate port? If your sysadmin isn't stuck in the > 80s and 90s, port 587 might work, whereas if AT&T is being even half way > responsible with their network, they'll have off-network port-25 access > blocked. If your sysadmin knows what he's doing, port 587 should work WITH AUTHENTICATION!! Neither port 25 nor 587 should relay mail from an off-network address to another off-network address unless the client authenticates itself.
DevilsPGD - 28 Aug 2008 07:56 GMT >> Have you tried an alternate port? If your sysadmin isn't stuck in the >> 80s and 90s, port 587 might work, whereas if AT&T is being even half way [quoted text clipped - 5 lines] >off-network address to another off-network address unless the client >authenticates itself. While true, the iPhone knows to use authentication on 587 automatically, which is why I didn't mention it.
In fact, at least on my config, it figured out 587 with authentication all by itself. I block 25 on my edge firewalls though, and I definitely did the initial config on wifi.
However, since port 25 was blocked from the start, I don't know if the iPhone tried 25 or 587 first, if 25 was available on one internet connection it might have been picked as the default and then become unavailable when changing to another connection.
Larry - 24 Aug 2008 05:22 GMT > For now, that's my solution. It galls me a little because my > own network server should properly be my main server, and their > network should handle this without making me work so hard, but there > you have it. The best mobile email comes from Google.....Just use Safari to access it.
David G. Imber - 24 Aug 2008 07:59 GMT >The best mobile email comes from Google.....Just use Safari to access it. Thank you for your advice. My own network also has a serviceable webmail application.
As I've written about this elsewhere, I don't mean to sound harsh and finicky, and I take no pleasure in slamming AT&T, but if I'm paying $60/month for data services on two phones, I want something stupidly simple and low-tech to work properly, rather than have to do something I didn't intend to in order to compensate for its not working.
Just my opinion. Thanks again!
DGI
Larry - 24 Aug 2008 17:03 GMT >>The best mobile email comes from Google.....Just use Safari to access it. > [quoted text clipped - 11 lines] > > DGI Ah, I see your point. I'd feel the same way. Webmail isn't rocket science, but then again it cannot be administered by someone who accepts pay like the janitor, either.
NightStalker - 24 Aug 2008 22:03 GMT > I inquired here a short while back about a persistent problem > I've been having with the iPhone. It fails to send mail sometimes and [quoted text clipped - 19 lines] > > DGI I suppose it's been mentioned before, but one way around the SMTP block is to make sure you set up your SMTP server as an Authenticated server, requiring UserID and Password. This doesn't work with ALL ISP blocks, but it works with mine, for instance.
I have my own email domain and server (hosted in Montreal, I'm in Australia) and I can use my own SMTP as long as I have it set up as authenticated. Before I did that, it was blocked.
If you've already done that, and still no joy, then have you tried talking to AT&T's tech support to find out just HOW you can get SMTP mail through an off-domain address?
If they have it blocked on the SMTP protocol rather than simple port blocking, then there is nothing you can do - you'll either just have to live with it, or change providers.
 Signature NightStalker
David G. Imber - 25 Aug 2008 05:57 GMT >If you've already done that, and still no joy, then have you tried >talking to AT&T's tech support to find out just HOW you can get SMTP [quoted text clipped - 3 lines] >blocking, then there is nothing you can do - you'll either just have to >live with it, or change providers. I try to avoid tech support conversations unless absolutely necessary. I find more knowledgeable people on line, including here.
The thing is, my own SMTP server works, but intermittently. So it's not a blocking situation.
Thanks, DGI
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