For some reason that I do not understand there seems to be a major issue with setting up Media Temple based email on a Mac running Yosemite. This issue is specific to the MacMail program as best as I can tell. After spending time with the wonderful folks at tech support and reading forums, I discovered the issue is a bug in Yosemite and it is flagging Media Temple as unsafe. In the steps below I will show you how to setup your iMap email and resolve this issue.
Step 1: Open Mail on your Mac
Step 2: Click on Mail
Step 3: Click on Preferences
Step 4: Click on the plus sign at the bottom left. This will tell the system that you are wanting to add a new email address.
Step 5: Fill in your name as you would like it to be seen by email recipients. You may want to sue your company name or your personal name. This choice is up to you but do know that people will see it.
Step 6: Put in your email address. My tip to you is to copy and paste everything.
Step 7: Enter your password for your email address. This password will be whatever you put in when you created the email address in your cPanel.
Step 8: Click on Create
Step 9: At this step the system is telling you that it needs more information. Go ahead and click next.
Step 10: Make sure that IMAP is highlighted
Step 11: Type in your mail server. If you are using Media Temple it may start with a K but double check your information.
Step 12: Your username is your email address.
Step 13: Copy and paste your password.
Step 14: Click Next
Step 15: Click on Show Certificate
This is the issue that we need to resolve today between a Mac running Yosemite and an email account supported by Media Temple. For some reason Macs have decided that Media Temple may not be a secure host. Of course Media Temple is an extremely secure host that I highly recommend. Do not think much of this, it is just a bug in the system.
Step 16: Click on Trust
Step 17: We need to tell our computer that we trust Media Temple. Click on each drop down and say always trust.
Note: When doing this tutorial I did not check always trust and therefore I have to repeat this process later, as you will see below. So go ahead and learn from my mistake and check always Trust.
Step 18: Your computer is going to prompt you to enter your master password to confirm that you really mean it. This is not your email password. This password is what you use to log onto your computer every day.
Step 19: Enter your email server information. If you are using Media Temple for your email then this likely starts with a K.
Step 20: Your username is your email address.
Step 21: Enter your email password (copy and paste).
Step 22: Click on Create
Step 23: Enter Port 587. If you are following along from your Media Temple mail setup instructions it is going to give you a different port for outgoing but this is the one that works.
Step 24: Make sure Use SSL is selected.
Step 25: Make sure that Password is selected.
Step 26: At this point your dialogue box should close down. Please close down your email completely.
Step 27: Reopen your Mac Mail
Step 28: Click on connect when this comes up
Step 29: Click on Trust
Step 30: Click on Always Trust
Step 31: Make all three of the drop downs Always Trust
Step 32: Click on Connect
Step 33: Enter your computer password
Step 34: Click on Connect
Step 35: Try sending an email.