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Martin HambalekMartin Hambalek 

Lessons Learned from 365/Okta Integration

We will be turning on the integration this weekend for our organization as a test to understand what the user can expect when we turn it on permanently. We know the integration will work, but we want to know what the user see or have to deal with once Okta is enabled. This will allow us to tailor communications and training materials.

Can anyone share with me their experience with Outlook desktop and moble, Sharepoint Online, Skype desktop and mobile, and any other 365 apps?  Any gotchas or changes in how users interact with those applications?
Alan JohnstoneAlan Johnstone
Make sure you enable modern authentication within various o365 apps or the user will be prompted for creds more often than they need.  I believe Skype, Exchange, and a couple others needed powershell to turn this on.  (Modern auth is what Okta is using)

We just went live about 6 months ago.  Originally with User Synch provisioning, then Universal Synch, then limitations caused us to install AD Connect and switch to roles/licenses only.

The Okta/o365 experience has been good so far.  Make sure you are running latest IWA or certain features won't work. (IWA must be encrypted, etc)   Playing with Conditional access now and device registration. 
Martin HambalekMartin Hambalek
We plan on turning on IWA later.  Is it required?