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

Select the Advanced tab in the settings for the account and check the box marked

Automatically detect and maintain account settings

Close the preferences window and save the change.

Also have this problem. Just after updating my two imacs at our office all mail accounts stop (IMAP) stop to connect to my mail server. I have also macbook air which I haven't updated yet, and the settings are identical. Though my macbook outgoing mail works like normal.

Seems like there is something Apple did in this update that corrupts the mail settings? I am thankful if someone have a sullotion for this?

Am having the exact same issues. The box in the Advanced tab is checked and still not able to send emails. They just "sit" in the outbox.

I have the same problem, and tried the same things, without success. In addition I ran Disk Utility and also tried Linc Davis' suggestion, about checking the box marked Automatically detect and maintain account settings. None of it helped. You have to be brave/foolish to be an early adopter! This is a pretty serious bug and I hope somebody discovers a simple solution for us.

Unfortunately as above suffering the same issue. Appears to be isolated to gmail SMTP server list...

'Other' email servers i.e. iCloud unaffected.

Another observation is that when you edit the SMTP gateway server list -> Advanced - the password is blank.(assuming this should have a entry)

After trying to reset this a few times it appears there is some process removes the password and resets to blank - frustrating...

I am in a similar position. Upgraded both OSX and iOS and now I am unable to send email using SMTP Port 587 SSL - not using GMAIL

Only using Mac Mail or Mail.app - I also have Outlook installed on my Mac and using the same account settings works fine.

Both worked prior to the update so it might seem the updates changed something with SSL or authentication.

I thought Apple would fix this on the final release for the 10.10.4 release. I experience the same issue with the 10.10.4 beta, so i have switch it back to 10.10.3. but then my photo library has been updated to 10.10.4 beta related.

so today, when the final version of 10.10.4 release, i updated so i can access my photo library. but it seems the smtp function will not work on mail. i have four different smtp account setting! none of those work

I discovered this problem shortly after applying the update this morning. I noticed the same problem a month or so ago with the developer preview and reported it. The company that I work for have their own email system with SSL secured SMTP server. We have had several help desk calls from people who did the update when they arrived at work this morning and have been unable to send email since. I've tried everything that I've seen on this forum plus some other things and here is the situation so far:

1) We have two ways to access the server, SSL and non-SSL. The non-SSL is not allowed offsite but works onsite. This makes me think the issue is SSL related.

2) The SSL certificate for our company email server is a self-signed certificate, i.e. not issued by Verisign etc. We do this to reduce cost because we have many servers and it has never been an issue before.

3) Installing the root certificate in Keychain and manually trusting it has no effect.

4) SMTP via Thunderbird works fine in both SSL and non-SSL mode so this is an Apple Mail related issue...

I'm going to continue to play with this (even though I should be getting work done now that we have a workaround (Thunderbird) I'' keep banging on this in the hope of a solution. I suspect it is just that Apple Mail no longer plays well with servers using certificates it doesn't trust.

Same problem here. We are unable to send mail using our mail server.

We've tried deleting the mail account completely and re-installing. No effect.

We've tried changing the settings to use SSL/No-SSL, port 25, 465, and 587 no effect.

We've tried setting to automatically mange changes, and not automatically save changes.... no effect.

This is effecting users on 10.10.4 who have taken the latest update.

We have a 10.10 in the lab that was not updated that is working fine, taking updates to see if the same thing happens to it.

When we use SSL port 587 (submission) logs fill up with:

Jul 1 10:37:48 postoffice sendmail[7360]: t61HbmbA007360: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

Jul 1 10:37:48 postoffice sendmail[7361]: t61HbmSA007361: [12redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA

Jul 1 10:37:48 postoffice sendmail[7362]: t61HbmkS007362: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to TLSMTA

Jul 1 10:37:48 postoffice sendmail[7363]: t61Hbmd4007363: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

Jul 1 10:37:48 postoffice sendmail[7364]: t61HbmiA007364: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA

Jul 1 10:37:48 postoffice sendmail[7365]: t61HbmuZ007365: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to TLSMTA

Jul 1 10:37:49 postoffice sendmail[7367]: t61Hbnx5007367: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

Jul 1 10:37:49 postoffice sendmail[7369]: t61HbnrR007369: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA

Jul 1 10:37:49 postoffice sendmail[7371]: t61HbnWm007371: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to TLSMTA

Jul 1 10:37:49 postoffice sendmail[7373]: t61HbnMR007373: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

Jul 1 10:37:49 postoffice sendmail[7374]: t61Hbnnb007374: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA

Jul 1 10:37:49 postoffice sendmail[7375]: t61HbnrF007375: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to TLSMTA

Jul 1 10:37:57 postoffice sendmail[7381]: t61HbvOI007381: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

Jul 1 10:37:57 postoffice sendmail[7382]: t61Hbv2V007382: [redacted] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA

I can partially support your observation, but can also add some weirdness:

- My private mail server is a courier-imap-ssl server with a self-signed certificate. From the moment of the update I haven't been able to connect to that server. Not via SSL. Nothing changed except OS X, and receiving and sending eMail still works with iPhone and iPad (Which I won't update for now) and for example with Thunderbird. Looking at the logs of my server O get weird SSL connection timeouts from my Mac.

- One of my professional mail accounts uses SSL with a self-signed certificate (it's a research institute, so money is short). With this account Mail still works without any problems, but I don't what kind of imap server they are using.

Have a lengthy session with the Apple support and level 2 support today

We finally get it working, but try it at your own risk!!!!!!!!!😕

We first backup the the V2 folder in the Mail in User/Preferences

then go to internet account in System Preferences, remove all the email account one by one

then go back to Mail to make sure all accounts have been removed

Quit and restart the computer

launch mail, add the most important email account and test the incoming and outgoing and it works

then slowly reimport all the old message from the backup V2 folder and make sure only import the mbox, if you have another level of folder inside that mbox

you should create a folder the same name, then move the sub directory mbox into that directory

for example

Folder A.mbox

-- Folder B.mbox

Folder A.mbox

Folder A (folder)

--- Folder B.mbox

I am still in process on this

My email setting, I use gmail as incoming server and third smtp service

I also have issue on the 10.10.4 beta, but at that time, I decide to switch back to 10.10.3

Clearly a big mistake upgraded to 10.10.4 Unable to send emails since upgrading, despite trying everything I could think of. At least it still works on my iPhone and on my macbook. Obviously a big bug with the new release. Look forward to a rapid resolution (ha ha)

This fixed all my mail accounts! Thanks for the suggestion.

you don't have to import message by messages, one mbox equal to one folder.

I wish i can go back to 10.10.3 but due to the beta locked up my photo library, really need to get back to 10.10.4 in order to access my older photo library

Good luck to you all!