Instructions For IMAP Email Server Settings with Mail Security Key

So, this past week I did a favor for my friend who is an attorney. I, myself, am an Apple Technician and do not touch Windows / Microsoft / Office / Outlook anything, simply because it is like pulling teeth do perform simple tasks compared to working in the Apple world.

My friend didn’t know what was wrong but he knew SOMETHING wasn’t working right. And I figured it out after a few minutes. It turns out that his Windows computer pulled “POP” mail settings automatically when we added it to Outlook. But both of his Apple products pulled IMAP settings correctly on initial setup. (Like they should have.)

So in this scenario of help for my buddy, I had 2 things counting against me. Not only is he using a email address for his personal email (which by the way is mixed up with and because of acquisitions, etc.), but he wants me to find out why it wasn’t working correctly in Outlook for Windows.

I already knew what I was getting into, but because he is who he is, I said I would do it. And after 1 hour and 45 minutes, I FINALLY got it to take my settings.

Why pretty much ALL of the articles you’ll find on Google will NOT work.

Out of 2 pages of Google searches with the term “email server settings for and Outlook”, not 1 of them had the answer. All of them were either vague, matter of fact (and wrong at the same time), or gave completely inaccurate, useless server setting information. And on top of that, not a single one mentioned anything about the “Security Key” that Bellsouth / added to their “security” a little while ago. And I use the word “security” loosely here, because bellsouth / att / yahoo and AOL to name a few, have been VERY late to the security game for their users / customers.

But anyways, in my case, the Security Key was detrimental to getting the manual server settings in Outlook to finally work. Below are the settings that worked for IMAP server settings in Outlook for Windows.

Step-by-Step Instructions For IMAP Email Server Settings with Mail Security Key

  1. The first thing you need to do is to go to (Yes, even though you have a account), and sign into your account. More instructions for this here:
  2. Once signed in, go to your PROFILE. (Usually in the upper right hand corner).
  3. Scroll down to the bottom of the page and look for Security Key. (Usually on the lower left side).
  4. Add / Create a “Secure Mail Key”.
  5. Once you see the key / code, make note of this because THIS is the password that Outlook will want, not your password.
  6. Make sure to click OK or SAVE.
  7. Now……..Open Microsoft Outlook 2016 and click File in the menu.
  8. Under Account Information, click + Add Account.
  9. Select Manual setup or additional server types and click Next.

Your Name: Enter Your Name (Example: Bob Smith)
Email Address: Your Email Address (Example:
Account Type: IMAP
Incoming Mail Server:
Outgoing MailServer (SMTP):

Logon Information:
Username: Your Full Email Address (Example:
Check Require logon using secure password authentication (SPA)

10. Now click MORE SETTINGS.
– General Tab: Name the mail account if you want.
– Outgoing Server Tab: Check the box that says “My Outgoing Server (SMTP) Requires Authentication / Use Same Settings As My Incoming Mail Server.
– Advanced:
Incoming Server (IMAP): 993
CHECK the SSL box or choose SSL.
Outgoing Server (SMTP): 465
CHECK the SSL box or choose SSL. Or try SSL / TLS.

Click Next and if all goes well, Incoming and Outgoing will pass the test and you will now be using IMAP settings, and all of your mail will synch like it should Email Settings Server Setup IMAP SMTP POP

I know that there is a chance that these settings will not work for you, but they finally worked for me, and it took a lot of testing and tweaking because every time you change a setting and test, it would take up to a minute each time just to tell you that the settings are wrong. So I hope that if this does not work for you, it at least puts you on the right track to solving your own settings issues.

Good luck.


ubermac previous recipients mac mail remove

In the past in Mac Mail, if a recipient populated, there was a little trick you could perform. And that was to add the old email address to the “To” field, and then click the little arrow next to it and choose “Remove From Previous Recipients List”.

Since Updating to OS X El Capitan 10.11, and then to MacOS Sierra 10.12, I had been noticing that it didn’t seem that option appeared anymore.

So I went to do a google search and the first few answers said got do exactly what I said to do above. But I know I didn’t see that option. So A little more digging and I found an even better, fool proof way to completely remove previous recipients. Read below for that process.

  1. First and foremost, you may want to go to that person’s Contact Card in your address book and make sure to remove or delete the old email addresses that you no longer want to show up.
  2. search your address book to make sure that the address in question isn’t in a random contact card as well.
  3. Open Mac Mail and choose “Window>Previous Recipients”.
  4. Search for the name or email address that keeps showing up and delete them from here.

That should do it. And if you need further help, contact us here. Hope this helped.