iOS 8.4 killed SMTP SSL/TLS over port 465?

in iPhone edited July 2015

I run an email system with 2500 users, several hundred with iPhones. Today I've started getting reports that after the 8.4 upgrade, they can no longer send out-going mail through our server. I've confirmed this on an iPhone 4S I use. The server accepts authenticated connections over port 465 with TLS/SSL.


Since the upgrade, the server logs the following for every failed attempt: [xx.xx.xx.xx] did not issue MAIL/EXPN/VRFY/ETRN during connection to TLSMTA


It would appear that the upgrade had done something to the SSL/TLS routines in Mail.


Anyone else seeing this?


  • Reply 1 of 6
    gsouthgsouth Posts: 1member

    I am seeing issues on all iOS 8.4 clients connecting (or rather not connecting) to an sendmail installation running SSL on standard port 587, I don't believe it's a port issue.

  • Reply 2 of 6
    arne2arne2 Posts: 4member

    OK, that's worse than I thought. I figured I'd try to enable 587 via STARTTLS on my system, but if that's not going to work either...

  • Reply 3 of 6

    I just confirmed this with a senior tech advisor.  He admitted they killed SSL/TLS "for more security".  If that isn't the most inane comment, I'm not certain what is.


    Does anyone know if any of the third party email clients will work with SSL/TLS?  Otherwise, Apple just lost a whole bunch of customers. 

  • Reply 4 of 6

    Same problem here when we disable TLS v1 on our mail server. 


    PC's can connect no problem using TLS v1.2, but iPhone/iPad will not connect. 


    Anyone have any ideas?

  • Reply 5 of 6
    arne2arne2 Posts: 4member

    Same issue on the in OS X 10.10.4...


    Killed SSL/TLS for "security"? that's insane.

  • Reply 6 of 6
    arne2arne2 Posts: 4member

    So here's my issue - we provide email services to numerous local school districts, their staff has lots of Macs and many iPhones and iPads. If I can't use TLS/SSL anymore, what do they think we should do? Move everyone to webmail? I don't think that's gonna fly.

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