HI Aaron,
I hope you are using Azure AD connect. If not install that. I will give you some links below, the most important one is where you have to add a couple of MS sites to your intranet zone via GPO. This will log your users ( to whom the GPO is applied), straight in. This is a working solution.
https://docs.microsoft.com/en-us/azure/active-directory/connect/active-directory-aadconnect-sso-quick-start -- gives the URLs of the MS web sites to be added via GPO
Test SSO connectivity. https://testconnectivity.microsoft.com/ -- This requires ADFS as it looks for ADFS to perform it's SSO tests. --- Very useful to test your connectivity levels and get an idea what's going on.
Hope this helps.
You need to set up a service account on AD that has Global admin permissions, login as that person to the server / computer where you install Azure AD connect. Then in stall AAD connect make sure your firewalls let the traffic through for that server etc.
You should be a happy person at the end of today. For me it took less that two hours after I found the above web sites and a re-install of AAD connect.
Best Wishes.
