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Level 1

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SMTP with SSL completely broken after iOS 8.4 update

Hello,

I'm an admin for a 500 user email system, about 200 of which are iPhones. All users who have updated to 8.4 are unable to connect to our secure SMTP server. This has never been an issue on previous iOS versions (server unchanged since 2011).

The server uses SMTP over SSL, MD5 Ch/Resp on port 587.

The sendmail server is logging the following on connection attempts:

Jul 3 10:30:36 mail1 sm-mta[23928]: STARTTLS=server, error: accept failed=0, SSL_error=5, errno=0, retry=-1

Jul 3 10:30:36 mail1 sm-mta[23928]: t63FUZlI023928: [***IP***] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

iOS 8.4

Posted on Jul 3, 2015 8:35 AM

Best reply

miluc

Level 1

13 points

Posted on Jul 4, 2015 3:20 AM

I had this too (1 iPhone and iPad). Workaround: switch off the Handoff feature did the trick for me.

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17 replies

eluis

Level 1

0 points

Jul 9, 2015 1:42 AM in response to GBat

That's my problem too.... I have an old system and updates are too dangerous by now as it may cause broken services.

I tried the instructions from weakdh.org too and didn't work too on my sendmail installation.

I think the problem maybe an outdated version of Open-SSL because I can generate successefully a 2048bits certificate.

It seems that the problem will only be solved with a fresh and recent OS installation.

Jul 9, 2015 7:38 AM in response to eluis

Well, here's an encouraging update. As mentioned earlier, fixing the cyphers as instructed at weakdh.org did not fix the problem on either my test iPhone or MacBook with 10.10.4 immediately.

But after the server tweaks, completely deleting the accounts and building them new from scratch did.

On the iPhone, I deleted methodically and completely - deleted the SMTP server first, then the entire account. I then powered off the phone completely and restarted it, then rebuilt the account from scratch, using the exact same SMTP settings as before (port 465, SSL on, password auth in my case). After the normal long validation, sending email works as it should again.

For the MacBook, I did similar, except I didn't reboot in the middle, just shut down Mail.app after account deletion. As with the iPhone, this process has restored SMTP ability to the MacBook as well.

The last bit is untested yet—now that the server has been remediated to Apple's liking, what will happen when the next iOS 8.3 device is updated to 8.4? Will it simply work as-is? Or will we need to delete and recreate the account on those devices as well?

SMTP with SSL completely broken after iOS 8.4 update