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iPhone/iPad SMTP Problems
Question asked by Scarab - 9/23/2014 at 11:09 AM
Answered
We have had multiple customers report that they are no longer able to send email from their iOS devices (although they are still able to connect via POP3 & IMAP with no problems). This all of a sudden started occurring last Thursday (nothing has changed server-side around this time), whereas they were able to connect via STMP just fine previously. Their iOS device gives the following error when trying to connect via SMTP:
 
 
"Cannot Get Mail
The mail server "smartermail.scarabmedia.com" is not responding. Verify that you have entered the correct account info in Mail Settings."
 
Here are the detailed logs of their SMTP connections:
 
[2014.09.22] 09:51:28 [70.199.143.143][30308871] rsp: 220 smartermail.scarabmedia.com
[2014.09.22] 09:51:28 [70.199.143.143][30308871] connected at 9/22/2014 9:51:28 AM
[2014.09.22] 09:51:28 [70.199.143.143][30308871] cmd: EHLO [10.183.4.86]
[2014.09.22] 09:51:28 [70.199.143.143][30308871] rsp: 250-smartermail.scarabmedia.com Hello [70.199.143.143]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250-STARTTLS250 OK
[2014.09.22] 09:51:29 [70.199.143.143][30308871] cmd: STARTTLS
[2014.09.22] 09:51:29 [70.199.143.143][30308871] rsp: 220 Start TLS negotiation
[2014.09.22] 09:51:29 [70.199.143.143][30308871] cmd: EHLO [10.183.4.86]
[2014.09.22] 09:51:29 [70.199.143.143][30308871] rsp: 250-smartermail.scarabmedia.com Hello [70.199.143.143]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250 OK
[2014.09.22] 09:51:30 [70.199.143.143][30308871] cmd: AUTH CRAM-MD5
[2014.09.22] 09:51:30 [70.199.143.143][30308871] rsp: 334 PC01NzQ2NDc4OTguNjM1NDY5NzYyOTAxNTQ1OTg2QHNtYXJ0ZXJtYWlsLnNjYXJhYm1lZGlhLmNvbT4=
[2014.09.22] 09:51:30 [70.199.143.143][30308871] disconnected at 9/22/2014 9:51:30 AM

[2014.09.22] 09:51:41 [70.199.143.143][57898536] rsp: 220 smartermail.scarabmedia.com
[2014.09.22] 09:51:41 [70.199.143.143][57898536] connected at 9/22/2014 9:51:41 AM
[2014.09.22] 09:51:41 [70.199.143.143][57898536] cmd: EHLO [10.183.4.86]
[2014.09.22] 09:51:41 [70.199.143.143][57898536] rsp: 250-smartermail.scarabmedia.com Hello [70.199.143.143]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250-STARTTLS250 OK
[2014.09.22] 09:51:41 [70.199.143.143][57898536] cmd: STARTTLS
[2014.09.22] 09:51:41 [70.199.143.143][57898536] rsp: 220 Start TLS negotiation
[2014.09.22] 09:51:41 [70.199.143.143][57898536] cmd: EHLO [10.183.4.86]
[2014.09.22] 09:51:41 [70.199.143.143][57898536] rsp: 250-smartermail.scarabmedia.com Hello [70.199.143.143]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250 OK
[2014.09.22] 09:51:42 [70.199.143.143][57898536] cmd: AUTH CRAM-MD5
[2014.09.22] 09:51:42 [70.199.143.143][57898536] rsp: 334 PC05MzUwMzAwNjkuNjM1NDY5NzYzMDIzODQ5OTg2QHNtYXJ0ZXJtYWlsLnNjYXJhYm1lZGlhLmNvbT4=[2014.09.22] 09:51:42 [70.199.143.143][57898536] disconnected at 9/22/2014 9:51:42 AM
 
[2014.09.23] 10:32:30 [70.199.137.210][53476531] rsp: 220 smartermail.scarabmedia.com
[2014.09.23] 10:32:30 [70.199.137.210][53476531] connected at 9/23/2014 10:32:30 AM
[2014.09.23] 10:32:30 [70.199.137.210][53476531] cmd: EHLO [10.179.192.49]
[2014.09.23] 10:32:30 [70.199.137.210][53476531] rsp: 250-smartermail.scarabmedia.com Hello [70.199.137.210]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250-STARTTLS250 OK
[2014.09.23] 10:32:30 [70.199.137.210][53476531] cmd: STARTTLS
[2014.09.23] 10:32:30 [70.199.137.210][53476531] rsp: 220 Start TLS negotiation
[2014.09.23] 10:32:31 [70.199.137.210][53476531] cmd: EHLO [10.179.192.49]
[2014.09.23] 10:32:31 [70.199.137.210][53476531] rsp: 250-smartermail.scarabmedia.com Hello [70.199.137.210]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250 OK
[2014.09.23] 10:32:31 [70.199.137.210][53476531] cmd: AUTH CRAM-MD5
[2014.09.23] 10:32:31 [70.199.137.210][53476531] rsp: 334 PDEzNjg1ODM3NzAuNjM1NDcwNjUxNTE5NjE1MDIzQHNtYXJ0ZXJtYWlsLnNjYXJhYm1lZGlhLmNvbT4=
[2014.09.23] 10:32:32 [70.199.137.210][53476531] disconnected at 9/23/2014 10:32:32 AM

[2014.09.23] 10:32:47 [70.199.137.210][7602651] rsp: 220 smartermail.scarabmedia.com
[2014.09.23] 10:32:47 [70.199.137.210][7602651] connected at 9/23/2014 10:32:47 AM
[2014.09.23] 10:32:47 [70.199.137.210][7602651] cmd: EHLO [10.179.192.49]
[2014.09.23] 10:32:47 [70.199.137.210][7602651] rsp: 250-smartermail.scarabmedia.com Hello [70.199.137.210]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250-STARTTLS250 OK
[2014.09.23] 10:32:47 [70.199.137.210][7602651] cmd: STARTTLS
[2014.09.23] 10:32:47 [70.199.137.210][7602651] rsp: 220 Start TLS negotiation
[2014.09.23] 10:32:47 [70.199.137.210][7602651] cmd: EHLO [10.179.192.49]
[2014.09.23] 10:32:47 [70.199.137.210][7602651] rsp: 250-smartermail.scarabmedia.com Hello [70.199.137.210]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250 OK
[2014.09.23] 10:32:48 [70.199.137.210][7602651] cmd: AUTH CRAM-MD5
[2014.09.23] 10:32:48 [70.199.137.210][7602651] rsp: 334 PC0yMTM5ODY5OTkuNjM1NDcwNjUxNjgyMzIzMDIzQHNtYXJ0ZXJtYWlsLnNjYXJhYm1lZGlhLmNvbT4=
[2014.09.23] 10:32:48 [70.199.137.210][7602651] disconnected at 9/23/2014 10:32:48 AM
 
I suspect that something happened with the recent iOS update that modified the way iOS devices connect via SMTP. Any suggestions on how to resolve this?

7 Replies

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1
Scarab Replied
9/23/2014 at 11:40 AM
Marked As Answer
I figured this out on my own.
 
Apparently the most recent iOS update changed all previous SMTP settings to MD5 Challenge-Response. The resolution is as follows:
 
  1. From the home screen on your device tap Settings, and then Mail, Contacts, Calendars.
  2. Then tap the email account under Accounts.
  3. Tap Account.
  4. Scroll down and tap SMTP under Outgoing Mail Server.
  5. Tap on your Primary SMTP server.
  6. Tap Authentication.
  7. Change MD5 Challenge-Response to Password.
  8. Tap the button on the top left to go to the previous screen, then click Done.
 
0
Steve Reid Replied
9/24/2014 at 5:35 AM
Would be nice if this thread simply turned into a Feature Request for Smartermail to handle MD5 Challenge-Response
0
Patrick Jeski Replied
9/24/2014 at 6:03 AM
Hmmm. iOS 8 didn't change my settings.
 
Edit - Oh yes it did. But I was able to send OK with it set to MD5 Challenge-Response
0
Steve Reid Replied
9/24/2014 at 6:35 AM
Well if it's working for pjeski then maybe it's something else
0
Michael Cummins Replied
10/31/2014 at 9:56 AM
We've run into this too. We're running 12.5.5409. Anyone have any additional insight?
0
Michael Cummins Replied
10/31/2014 at 11:55 AM
In our case it was an old entry in SMTP Blocking that was ineffective in version 11 and forgotten about, but quite effective after the upgrade to 12.
0
Bruce Barnes Replied
10/31/2014 at 1:07 PM
Are you running SSL? If so, that's the reason the MD5 Challenge-Response was successfully connected.

The iOS 8 edit of all mobile device settings is part of Apples updated security settings. Unfortunately, they rarely tell users that their settings will be modified when they update and it's up to the users to figure it out.
Bruce Barnes ChicagoNetTech Inc brucecnt@comcast.net Phonr: (773) 491-9019 Phone: (224) 444-0169 E-Mail and DNS Security Specialist Network Security Specialist Customer Service Portal: https://portal.chicagonettech.com Website: https://www.ChicagoNetTech.com Security Blog: http://networkbastion.blogspot.com/ Web and E-Mail Hosting, E-Mail Security and Consulting
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