10.10.4 Mail SMTP problem

interesting....

I can confirm that the final release of 10.10.5 does not fix this bug.

Hi, I had the same problem and I tried many many suggestions and tricks I found here and on the web.

But none worked for me. I spent the whole night making several attempts but unfortunately I could not send mail.

I use an iMac and updated Yosemite to version 10.10.5: unfortunately I did not know about the problem with the SMTP authentication, otherwise I would not have made the update.

In the end, I was thinking to restore the iMac from a TimeMachine backup because I didn't knew what to do anymore.

But first I wanted to try last possibility and it works fine for me: I hope it will be helpful to those who still have not solved the problem.

That's exactly what I did:

1. I configured the mail and the SMTP server on a MacBook with Yosemite 10.10.2 and everything worked properly.

2. Then I tried this on my iMac with Yosemite 10.10.5 (from which I could not send mail):

- Quit out of the Mail app

- From the OS X Finder, hit Command + Shift + G and enter the following path:

~ / Library / Mail / V2 / maildata /

- There is a file called "Accounts.plist" and I made a copy of it to my desktop (it's important, do not forget to do this)

- Open, in the MailData folder, the file named "Accounts.plist" with TextEdit

3. I compared the section "<key> DeliveryAccounts </ key>" (it is at the beginning of the file "Accounts.plist") with the same file of the MacBook (which provide email working properly) and I saw that there were differences.

I made several attempts and at the end I was able to send mail correctly from my iMac with Yosemite 10.10.5, without downgrading to 10.10.2.

Please, check the png file attached for instructions.

I think it's a bug and hope that Apple will fix it as soon as possible. It was very frustrating....

Hope my solution will be helpful to you.

Bye,

Giovi

I also have this problem and since I noticed some inconsistence when editing Accounts.plist manually and via appleMail's settings, I dug some more and found that Mail also changes settings in /Users/<username>/Library/Containers/com.apple.mail/Data/Library/Preferences/com.apple.mail.plist .

When these "container" settings are used?

Are they corrupt if smtp server's port is listed as "string", etc. and might this affect how appleMail behaves?

My authenticating smtp settings also has "automatically detect" checked but grayed out, so I can't uncheck it...

apparently this works because you have disabled secure authentication - AllowInsecureAuthentication > false

Just to confirm that 10.10.5 update did not fix Mail SSL issue for me

Managed to fix my issue, here is how:

Go to Mail > Preferences > Accounts
Select your account, go to SMTP > Edit server list
Delete SMTP server account completely and restart everything
Create the account again

Before making the changes that I wrote above, I tried to change only the tag "AllowInsecureAuthentication" from true to false but I couldn't send email, the problem was still there. And I tried also all the possible solutions other people wrote but the only solution that worked for me is what I wrote.

I upgraded to Yosemite 10.10.5 and in that moment started the problem, so I suggest people not upgrade to 10.10.5.

I know that remove and install account again works but I didn't consider this solution: I have 4 accounts IMAP and tens of thousands of messages stored in different sub directory so I preferred to find another solution.

Not the account, only SMTP server used needs to be deleted and then created again, IMAP stays intact and all messages as well :>

That solution didn't' work for me: I have 3 STMP server accounts, I deleted them and create them again but I couldn't send email.

As I wrote, the only solution that worked for me is the one I posted.

Thanks anyway for your feedback.

ackiid wrote:

apparently this works because you have disabled secure authentication - AllowInsecureAuthentication > false

You mean unchecking "Allow insecure..." removes graying-out from "Automatically detect.." and then I can once again uncheck it?

Sorry, doesn't work.

joedjjjjj wrote:

I can confirm that the final release of 10.10.5 does not fix this bug.

Not for me either.

Uncheck it didn't work for me too. That's why I published those instruction above.

If you have "automatically detect" checked but grayed out (as I had), you have to try to modify the accounts.plist file manually but before remember to close the Mail.app.

giovi73 wrote:

If you have "automatically detect" checked but grayed out (as I had), you have to try to modify the accounts.plist file manually but before remember to close the Mail.app.

Modifying /Users/<username>/Library/Mail/V2/MailData/Accounts.plist doesn't change a thing in my Mail.

But editing /Users/<username>/Library/Containers/com.apple.mail/Data/Library/Preferences/com.apple.mail.plist does.