Q: os x update 10.10.4; mail won't send 6/30/15

Thanks!  This gave me a clue as to where to look.

PeetDeVos wrote:

 

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

Thanks!  This is what fixed it for me.  I also run my own mail server.

Thanks PeetDeVose (your awesome)!!

That fixed it for me. In my case on Fedora Core first generated the 2048 DH pem file:

# cd /etc/pki/tls/certs

# openssl gendh -out dh_2048.pem -2 2048

Then added the following line to /etc/mail/sendmail.mc:

dnl # Added to resolve issues with Mac Mail

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

Then issued the command:

# cd /etc/mail

# make

# systemctl start sendmail.service

-or (Fedora Core older than 18) -

# /etc/init.d/sendmail restart

Apple provided this update:

Use modern cryptographic practices when setting up SSL and TLS services on your server - Apple Support

"To ensure security and privacy for your users, and interoperability with Apple products, server administrators should use a group size of 2048 bits or greater when using Diffie-Hellman key exchange. ...devices no longer connect to servers or webpages that are set up using weaker Diffie-Hellman encryption"

Again, using a 2048 Bit Diffi-Hellmann key may solve the problem for some servers. But there is another problem:

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] >> EHLO  (19 additional bytes)

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-my-server.de

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-PIPELINING

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-SIZE 110000000

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-VRFY

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-ETRN

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-AUTH PLAIN LOGIN

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-AUTH=PLAIN LOGIN

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-ENHANCEDSTATUSCODES

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250-8BITMIME

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 250 DSN

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] >> AUTH  (5 additional bytes)

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 334  (12 additional bytes)

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] >>  (12 additional bytes)

Jul  3 15:38:52 garion Mail[46508] <Debug>: [0x60000017ee40] << 334  (12 additional bytes)

Jul  3 15:38:53 garion Mail[46508] <Debug>: [0x60000017ee40] >> * (0 additional bytes)

At this stage it is already connected, but Mail sends an empty password. This is another problem.

Thanks Henningm,

So it turns out to not be a bug, but a security fix .

If it's a security fix then why haven't they fixed their own iCloud email service?  I have emails sitting in my outbox from my iCloud, Gmail and work accounts and none of them will go since I updated to 10.10.4.

An Apple support person contacted me as a result of my posts here. A potential terminal command to fix the problem didn't work. I've sent diagnostic logs to him and I'm waiting for a solution from him or from the administrators who look after the mail server that I use.

In the meantime, overnight, my laptop has inexplicably updated itself to 10.10.4. And so I've lost the ability to send mail from my main account again. I'm traveling and so I can't revert to 10.10.3 using my time capsule. This is very frustrating.

I can send mail through several other lesser-used accounts, including gmail and yahoo. It's only my main email, run through a university server, that won't connect with 10.10.4. And so it seems to be the encryption problem that has been mentioned in this thread. The administrators who look after that server have been working on a fix but want to make certain the fix doesn't disrupt other users' computers.

I Can't tell you why, but starting Mail with the SHIFT key pressed fixes it for me. That tip came from Apple Support

Using the shift key pressed doesn't work for me. The problem isn't the settings on my computer. It seems to be the lower level of encryption that the current outgoing mail server requires, and the higher level of encryption that Mail requires in 10.10.4. Starting up with the shift key pressed does nothing to fix that incompatibility.

As mentioned, my gmail and yahoo and another mail account on a private server are working fine. Those servers evidently use the higher level of encryption. But my main account, which is run by a university, uses a lower level of encryption, and the outgoing mail server won't respond to Mail.

So, a nice senior tech from AppleCare contacted me after reading this thread and asked if I'd be willing to reinstall 10.10.4 and produce some logs for her. No cure was suggested or provided, and nothing happened differently: I still couldn't send from any of my accounts.

But afterwards, stuck with the same problem and heartened by a few of the tales of success I'd read here since my last post, I thought I'd give it another try. I have the following four email accounts:

•iCloud,

• two Gmail (one regular, one Google Apps), and

• FastMail.

All are IMAP, so deleting and reactivating didn't put me at risk of a major reconstruction job.

Trying to delete an account by clicking the minus sign in Mail>Preferences>Accounts sends you to the Internet Accounts pane of System Prefs. One at a time I subtracted them there (which basically just grays them out). Then, back in Mail>Preferences>Accounts, I reenabled them by clicking "Enable this account." And one at a time, they all worked, that delicious whoosh of a successful send.

I'm happy to report that the problem preventing mail from being able to send on one of my accounts has been solved.

It was, as reported earlier, the problem of the new, higher level of encryption that Apple is requiring on smtp servers. The university IT people have adjusted the server to meet the new level of encryption, and it is now accepting connections from my iPhone, laptop, and desktop.

As I mentioned earlier, gmail, yahoo, and another mail account were working fine throughout this. It was just my main account, a university server, that wasn't working.

Deleting and readding accounts or using the shift key or disabling SSL (etc.)were not solutions because it wasn't an issue of outdated preference files etc. It was that Apple requires a higher level of encryption now that some servers aren't currently using.

I'm happy to say that just quitting Mail and restarting it by holding down the shift key did the trick me.  My email accounts are with Earthlink and gmail and I can usually fix things on my mac but this time none of the menu-driven solutions worked.  I am an old lady and relatively fearless when it comes to computers but I draw the line at going into the system and messing with files and commands that I don't understand.  Fortunately I am brilliant at reading the message boards and chats and I thank all you geniuses for having helped me once again!

Hooray! It's working for me too, although I keep checking the App Store for a proper fix.

And incidentally, I have tried a few other email programs designed for OS X and been sorely disappointed.

I was locked out of gMail IMAP and SMTP (I use dual authentication). Ticking the check box for Automatically detect and maintain account settings sorted it.

Unfortunately I had had problems with a another account and had been advised to uncheck all those boxes!

So now they are unchecked except for gMail where I have them checked.

C.