Set Up a MAPI Account in Outlook 2016 or 2019 for Windows

Regardless of whether you're using Microsoft Outlook 2016 or Outlook 2019 for Windows, setting up an account is exactly the same. However, there are a few pre-requisites you'll want to follow prior to attempting to set up your MAPI account in Outlook:
  1. MAPI/EWS requires a valid SSL certificate for the domain -- either a wildcard covering the domain as a whole, or an individual certificate for the mail domain.
  2. You'll want to make sure that the MAPI/EWS add-on is activated on the server.
  3. You'll want to make sure autodiscover is enabled for MAPI/EWS on the domain.
  4. You'll want to make sure MAPI/EWS is enabled for the account you're going to connect.
Adding a MAPI Account to Outlook
Once you've made sure the above is set up properly, you can add your account in Outlook. To do this:
  1. Open Outlook.
  2. Either use the default Profile Outlook gives you (named, appropriately enough, "Outlook") or create a new Profile for this account.
  3. If you want, you can choose to have Outlook prompt you for a specific profile when it opens, or you can set Outlook to always open a specific Profile -- it's your choice.
  4. Enter the full email address you want to set up.
  5. Click the Next button.
  6. You may be presented with an Advanced Setup modal -- select Exchange from the list of options if you are. (Office 365 may be selected by default -- BE SURE to change that select to Exchange to set up a MAPI connection to SmarterMail.)
  7. If you are prompted with a certificate warning, click the Yes button to accept the certificate. (This will generally only occur if you haven't accepted a connection that uses the same SSL certificate before.)
  8. During the set up process, you'll see a Windows Security modal that asks for a password -- input your mail account password and check the box to "Remember my credentials". Checking this box saves your credentials in Windows Credential manager.
  9. Click the OK button.
  10. After you input your password, Outlook will ask you to set your sync settings. This, essentially, is telling Outlook how far back to go to sync your account. By default, 1 year is selected, which is a good place to start. If you have a large mailbox -- say, 5GB or more -- you may want to limit the sync to 6 months or less, if possible. Regardless, you can always change this in Account Settings once the account is set up.
  11. Click the Next button.
  12. You will automatically have the account set up in Outlook, and should see the following window:
  13. Clicking the Done button will open Outlook -- if you have Outlook set to select a Profile each time you open it, you'll have to select your newly-created Profile from the dropdown menu. Otherwise, Outlook should open and start syncing to your SmarterMail account.
Troubleshooting
MAPI integration with SmarterMail is not without potential issues. This is primarily due to how ingrained Outlook for Windows is in the Microsoft ecosystem, Office 365 in particular. We worked long and hard to try and avoid any possible roadblocks, but there are some that even Microsoft can't help resolve. So, below are some potential issues you may run into, and the steps we've found that can help work around those issues. [THIS DOC WILL BE EDITED REGULARLY AS ADDITIONAL ISSUES ARE FOUND]

When using autodiscover, I'm prompted with a Microsoft Office login window as opposed to a Windows Security modal
This is probably because the domain you're using either was on Office365 in the past, but isn't now, or you're using Office365 for the online productivity suite, but not the Exchange portion. As such, Microsoft has cached the domain in its internal systems and is therefore defaulting to Office365 when doing its own lookups.

If you're running something like Fiddler when you're trying to connect your account, you'll notice that, regardless of the domain being used, Microsoft pings it's own systems first before moving on to any autodiscover or other DNS lookups during the account set up process. If it finds your domain in its cache, it assumes you're trying to connect to Office365, so it prompts you for your Office365 login credentials. (This opens in a small browser window whereas the Windows Security modal is an actual system modal.) To get around this, you can try one of the following:
  1. Simply click the X in the Office365 login modal -- this should cancel that login attempt, prompting Outlook to do a normal autodiscover lookup for the domain. If that does NOT work, 
  2. Cancel the set up and restart the process, but this time try setting up the account manually, avoiding any autodiscover lookups.