ArcGIS Online won't connect from ArcMap or Catalog

After several days of interaction with ESRI tech support it turns out that the issue stemmed from having setup an organizational account with ArcGIS online after already logging in at one point with a personal account. Because the organization was not setup at the same time as the first initial install, I had only the default portal connection (www.arcgis.com) setup in the ArcGIS Administrator App.

The fix was...

• Load the ArcGIS Administrator app
• Click the "Advanced" button
• Click "Manage Portal Connections"
• Add our personal organizational account domain to the list of connections.

The list now contains both the default "http://www.arcgis.com" and our organizational domain "https://www.xxxxxxx.maps.arcgis.com"

This seems like such a simple problem in hind-sight... It's hard to believe it took this long to resolve.

I've noticed now that it seems that ArcGIS Online doesn't like named user accounts to switch on a single install which makes total sense. My situation was a result of my company using ArcGIS for years but having never setup an organizational account until recently.