Serious iPhone SMTP Issues - cannot send

telecomputers
Posts: 43
Joined: Sat Dec 04, 2004 3:59 pm

Serious iPhone SMTP Issues - cannot send

Postby telecomputers » Tue Jan 31, 2017 5:45 pm

We are getting calls from iPhone users who are unable to send email from their devices.
It would appear new iPhones (and perhaps a recent update) has changed the way their SMTP settings are configured on the phone.
I read that it automatically uses the format username@hostname instead of username@domainname.com - we have been unable to get anyone configured to be able to send outbound. They can get mail in but not send. We really need to resolve this ASAP.

Has anyone else figured out how to get this working? I'd appreciate any links to step-by-step or images of SMTP configuration screens that work.

I sent several clients to their Apple store with the complete configuration settings and even their own "geniuses" couldn't get it working.

I saw where there is supposed to be a "new" IMAP set up function on the WebMail page to automatically do the configuration - but not having an iPhone I cannot see if this exists and if it is working (with this seemingly new iPhone issue).
j@mes

MEpro 9.61
JAM Software - SpamAssassin in a Box
ClamAV / Sanesecurity

cjard
Posts: 35
Joined: Wed Jan 04, 2012 5:55 pm

Re: Serious iPhone SMTP Issues - cannot send

Postby cjard » Mon Feb 27, 2017 3:23 pm

Ask your iphone users to report on what their following settings are for your mailserver (settings.. mail.. accounts.. <the mail account>.. account.. outgoing mail server.. primary server..):

Use SSL y/n
Authentication (can be: password, md5 digest, md5 CR, ntlm)


For me, a recent iOS update changed all co phones to use_ssl=y, auth=md5challenge

telecomputers
Posts: 43
Joined: Sat Dec 04, 2004 3:59 pm

Re: Serious iPhone SMTP Issues - cannot send

Postby telecomputers » Mon Feb 27, 2017 5:42 pm

Thanks for the reply. I should have come back in and posted that we had resolved this.
We were a bit too aggressive in blocking at the HELO level (SMTP | Properties | Security tab} and blocked what appeared to be 100% spam coming from:
[*.*.*.*]
It turns out that some smartphones use the bracketed IP address format for their ELHO - HELO information.
Once we unblocked that the phones all began working again.
Unfortunately about 99% of the HELO formatted this way are spam.
j@mes

MEpro 9.61
JAM Software - SpamAssassin in a Box
ClamAV / Sanesecurity

cjard
Posts: 35
Joined: Wed Jan 04, 2012 5:55 pm

Re: Serious iPhone SMTP Issues - cannot send

Postby cjard » Thu Mar 02, 2017 4:44 pm

You might still be able to block a lot of these with a script (Advanced SMTP tab, Edit Script) as the script can examine the HELO that was sent, but only after the mail from command is issued/whether the sender is authed..

At a guess you might want to bin 100% of HELO matching [*.*.*.*] where senderauth is 0

Only thing I'm not clear on, is that ME classes this inder the SMPT "Inbound" tab and I don't know what they mean by inbound - if they run the script upon every incoming data, then it will work.. If they run the script after determining the mail itself is "inbound" (= has a RCPT TO: address that is destinated for a mailbox in a local postoffice??) then it wouldn't work.. Or maybe it would because it won't run for you iPhone users as they're "outbound"ing..

Worth a try I guess, though be warned that scripting in ME is kinda horrible, really hard to debug and things sometimes don't work as they should even though it reads OK

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