O SX Yosemite 10.10 Smtp Mail Problem

I am now on 10.10.2 and still having mail issues, I have to say I though this app was going in the right direction with Snow Leopard but now think it is a total mess of an application.

Apart from all the other issues and gripes the main problem I have is with SSL connections, I have several accounts some POP some IMAP, the POP accounts that connect using a secure connection and the IMAP accounts that use SSL settings periodically have connection issues, all at the same time. None of the suggestions offered actually seem to help, even selecting the 'Use a non secure connection' checkbox. I am bewildered that at 10.10.2 even simple things like Mail remembering settings have been changed and asking the user to save before leaving the account settings... this has still not been fixed and so creates even more confusion with all the other issues.

I can get mail to connect to these SSL accounts again by restarting the laptop, restarting mail does nothing to help but as I mention... I have found restarting the computer then brings these accounts back online, at least until whatever it is that mail is using from the computer system goes into a wobble again!

HTH

1: Fix Sending Mail Errors in OS X Yosemite with Credentials

If you’re getting cannot send mail errors only when trying to send mail or connect to your emails SMTP server, the solution is probably the same as when Mail repeatedly asks for a password, you simply need to re-authenticate and provide the SMTP server your login and password as set in the mail preferences:

1. Now click “OK” and close Preferences, selecting to “Save” when asked about changes
2. Compose a new email message and send it (to yourself, us, your Mom, Santa, whoever, this is just a test email)

The email should now send as usual.

Once that email goes through, you may have some unsent messages sitting in your outbox, they will send automatically in time, but you can also synchronize the mail account to push it along.

Im running on macbook pro OS X Yosemite 10.10.2 and my outgoing mails were stuck for days although i can send from my iPhone, here is what worked with me:

Unchecked Automatically detect and maintain account settings

Unchecked Use SSL

Checked Allow insecure authentication

Re-entered my username and password (not sure if that having anything to do with it)

Port 25

TLS Certificate None

Anyone have a solution for this yet? Wow lots of problems and no apple solution. I love my apple products but this one is not good. I get emails but can't send. I upgraded because I was having trouble with mail on prior version, wish I would not have upgraded.

I am pretty used to email account issues, and usually know what to do. My wife's apple mail stopped sending, and I tried most all of the solutions I have read. I got on with AppleCare level 2 support. After a couple of hours of more of the same, we decided to delete and reinstall the accounts. It's not hard. BUT (!!!) that only worked for a couple of days. The password would disappear in the smtp section. I finally called the Apple repair shop where we have gotten more memory and hard drives. These guys are great (Chesapeake Systems in Baltimore). Here is what they had me do:

Go to Applicaitions>Utiltities>Keychain access. Find all passwords that resemble email passwords. They usually have the blue circle with the white @ in it for ACCOUNTS. Delete them. At least for the time being this has resolved our issue when none of the other things did (because re-entering the password would not take). I hope this helps. Mostly, I hope Apple makes this much easier. To me it is strange that we can all entere our email accounts on our iOS devices with so much ease, and our computers feel like a Windows nightmare from the 90s. Get on it, Apple!

Hi, I also have a lot of problems with mail since the upgrade

tried:

- deleting the envelope index files

- turning off the automatically detect and maintain account settings

furthermore I was not happy with the fact that my iphoto application was gone and the file still there. the new iphoto is not as user friendly as the old and has less functionality. takes some time to figure out things as well.

any help with the mail problem is well appreciated...

This appears to continue to be problematic for some folks in 10.10.4. There's some interesting behind-the-scenes details about what's (not) actually happening when the Mail app is trying to send mail: 10.10.4 Mail SMTP problem

I'm just a little startled that it's been going on since 10.10 and hasn't been fully addressed. However, it doesn't seem to be universal, but rather hit-and-miss as to who inherits the issue, and who doesn't, as well as when it might hit.

It's now 2015, having all of these issues in Yosemite.... did yours ever resolve in 2014? what did you do?

Now it is 2016, Just loaded 10.10.5 and it broke my email again. This time I have spent 4 days and I can not get it back up and working. I have tried so many things, and nothing really worked. I was able to create a a new account and get it to work until mail was restarted then smtp die again and went offline line again. From what I am reading El capitan is having problems to.... Apple knows about this, either can't or won't fix the problem. The software is not viable, so it it time to start to find find 3rd party software.

From what I am reading the 3rd party software is not very good either. the 2 best that I see are:

.. postbox is 40 (discount to $32) has feature, no documentation, poor support that costs money.

.. Mailmate is $50 plain text feel, map only, not user friendly, but it works.

both have free 30 trial periods.