iPhone "can't send mail...invalid e-mail address"

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

In article <fbl1b4pcea73o3bmhl84bn6j35b4ack1ma@4ax.com>, David G. Imber
<imber@maniform.com> wrote:

> 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

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 <imber@maniform.com> wrote in
news:fbl1b4pcea73o3bmhl84bn6j35b4ack1ma@4ax.com:

> 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.

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

On Sun, 24 Aug 2008 04:22:02 +0000, Larry <noone@home.com> wrote:

>
>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

In article <uv02b410gurljv0mqca2uilnsmp71sbll6@4ax.com>, David G. Imber
<imber@maniform.com> wrote:

> 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.

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.
>
> 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.

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.

In message <uv02b410gurljv0mqca2uilnsmp71sbll6@4ax.com> David G. Imber
<imber@maniform.com> wrote:

>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.

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 <imber@maniform.com> wrote in
news:9a12b4d5j5vbnoadei47cgmmqdmm6ut4dt@4ax.com:

> On Sun, 24 Aug 2008 04:22:02 +0000, Larry <noone@home.com> wrote:
>
>>
>>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
>
>
>

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.

On Sun, 24 Aug 2008 19:27:41 +1200, Anybody
<anybody@anywhere-anytime.com> wrote:


>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

On Sun, 24 Aug 2008 03:51:47 -0600, DevilsPGD
<spam_narf_spam@crazyhat.net> wrote:


>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