Q: Mail not working after update OS X 10.10.4 and IOS 8.4

NOTE: I fixed the Sending Issue on Server side.

I've had the same issue as all (10.10.4), but the issue was on the Mail Server, not Apple Mail.  This was a big pain, but I was able to fix the issue on the Mail Server side (since I'm the administrator).  This post is for Mail Server Administrators using Sendmail.

Sendmail server on CentOS / Linux:

I added the following to the /etc/mail/sendmail.mc file before re-make (make -C /etc/mail) and restart of sendmail only (service sendmail restart).  It instantly worked:

dnl # Added to resolve issues with Mac Mail

define(`confDH_PARAMETERS',`/etc/mail/certs/dh_2048.pem')

Before you do that, create the dh_2048.pem file using (openssl gendh -out dh_2048.pem -2 2048) in the relevant path (/etc/mail/certs or what you use).

I hope this helps,

Regards,

Peet

Hello MwarkV,

In Account Information go to ' Outgoing Mail Server SMTP ' near the bottom, click Edit SMTP server, new window opens, make sure you are on the correct server from the list, then click ' Advanced ' In Advanced turn off SSL which worked for me but you may also need to set Authentication to ' None '.

Hope it works !

M

OK

I have one POP3 and three IMAP Gmail accounts. The POP3 is fine, all the Gmails stopped working after the 10.10.4 upgrade.

I tried various things suggested above.

The only thing I find works is to go through each of the accounts, in Preferences>accounts>edit the outgoing SMTP server and under advanced, re-enter the correct password.

This works for all three accounts ONCE, and for two of them all of the time.

So, for the one that does not work (its outgoing server now showing Off line), I use one of the other Gmail accounts outgoing servers!

This works a treat.

These **** SMTP / Password issues started with Yosemite. Strangely enough, so did the reordering of email account in the Apple mail account!!!

Spooky or what? If you look at the order in mail vs the order in preferences vs the order in accounts vs the order in the Edit SMTP server list, they are NOT the same.

I wonder if the stupid mail programme is getting its index knickers in a twist and is sending the wrong password to Gmail?

Sort it out Apple

I have only had the Mac a year, transferring from a PC. Now I wis I had just used MS Outlook.

Happy days guys

Tony

Thanks Michael for this.

Hello Everyone, mine is working already!

The problem I encountered was having an unsigned certificate (due to internal routing of web traffic etc). The solution is, on the Invalid Certificate prompt when Mail Loads, on the details, tick the box to disregard the  Invalid Certificate.

Hope this helps

Hello Tony,

Please don't give up on Mail just yet, i've been using it for years & years with virtually no issues at all.  This is a are one. In fact my problems this time were solved by simply turning SSL off on the Outgoing mail server.

Regards,  Michael

Hi

I had another go (Thanks Michael Prior), since my solution may have sent emails, but from the wrong address and nothing synced (is that a word?)

So,

- I found this Google website:

https://productforums.google.com/forum/#!topic/gmail/Ihf4CiAb0ys

- I gave it 20 minutes (to allow the password attempts to cool down) and followed the instructions

- I Went back to edit the ingoing and outgoing servers, using my correct password

- Then, In advanced, I ticked "Automatically detect and maintain account settings" (this greys out IMAP.GMAIL.COM)

- I saved it

And it all works again

Phew!

Cheers

One Happy Tony

I're sure that this is WAAAY too technical for  most users including myself.

The simple : HOLD THE SIFT DOWN WHILE STARTING APPLE MAIL solved my problem.

It's truly unbelievable how this made it to "market".  It's inconceivable that this issue  would not have been raised in even MINIMAL beta testing....

How could Apple allow this product out without sufficient testing.

This sort of testing insufficiency was demonstrated at previous releases of OX X

APPLE ??????... come on now...please explain this...

Hi Oldcritic.  I have the same situation.  I called Cableone and they told me that I need to wait a week for some sort of upgrade, and to use webmail in the meantime.  I hate webmail.  Did you find a solution ?   Thanks,  Paul

SO I turned off the "ssl" feature in the settings outgoing server/primary server and I am now sending email. Problem fixed for me. I was on a IMAP email account and my hot and yahoo were unaffected ( iPhone 6). This worked despite the fact that this setting was the same in iOS 8.3.

GIve it it a try for those who are still unable to "send."

Hi Everybody,

I'd just like to mention that: No SSL = Not a good idea.

To switch off SSL is a temporary solution, but in the long run, its best to get the SSL/TLS fixed/patched on the Mail server side.

This is technically not a BUG, but a security fix by Apple.  They are not allowing weak security keys anymore ("Logjam" vulnerability).  See Use modern cryptographic practices when setting up SSL and TLS services on your server - Apple Support for more detail. 

So, if you think about it, disabling any form of secure connection to get around a weak security issue is not helping.  We're on the spot because we did not have a heads-up about this security update, but its really not Apple's fault that they are closing vulnerable security holes. This is how the world works .

My suggestion is to log a ticket/issue with your service provider and ask them to fix the issue on their side.  They basically have a security breach (send them the above Apple notice).  I was not aware of the issue on our mail servers, and this was how I was forced to fix it (see my post above for detail on how to fix it).

I hope this helps.

Regards,

Peet

I've had this problem for a couple of months now - even with 10.10.3. I don't think it has anything to do with smtp or settings like that....

I fire up the mail program; and there are NO EMAILS AT ALL in any of the folders, including the ones on my mac that I created

to save important emails.

then I get the spinning wheel when i try to quite; and, then I have to force quit.

in 10.10.3 i would get the 'Report to Apple'. Now, I don't even get that.

I think it has something to do with the email folders 'rebuilding' every time you boot the mail program.

sometimes the program just doesn't find them, for some reason. 'Pointers are off'.

Very annoying that they having fixed this. I've sent about 30 reports to Apple since this started happening.

Then, every once and awhile it just boots ok......maybe i should just leave the mail program open all the time........

I've had exactly the same problem for a month or two using 10.10.3, but it happens more frequently with 10.10.4. Starting Mail with the shift key held down has worked on the two or three occasions when I've tried it. This is on a Macbook Pro that is used mainly by my wife. I've only suffered the empty mailboxes once on the iMac, which uses exactly the same operating system and version of Mail. I wouldn't like to turn SSL off because that would lose a layer of security.

Thank-you Damo Clark.

Installed the 10.10.4 upgrade today - mail immediately stopped synchronizing on all accounts.  I applied your fix below and now mail is working.

The way I fixed it was to go into preferences for Mac Mail, and then Accounts.  Then for each mailbox, go to the advanced tab and tick "Automatically detect and maintain account settings".

I then saved the configuration changes and restarted Mail and my accounts started working again.

I'm pleased for you that this helped, but I've always had that box checked, and it hasn't always enabled mail to open with folders populated by emails

LIFE SAVER.  That is all.

Many thanks - the serverside change on CentOS fixed it.