You just re-enabled IWA DSSO and notice it's not behaving as it should. What is an aspect you should keep in mind?
Solution: That when re-enabling IWA DDSO you have to issue another API token for the AD / IWA Agents
With agentless DSSO (Desktop Single Sign-on), you still have a need of deploying IWA Agents in your Active Directory domains to implement DSSO functionality.
Solution: The statement is true, as agentless DSSO means no AD agents, not no IWA agents
After you turn on Desktop SSO, a default DSSO related routing rule is created. You must configure the network information for this rule.
Solution: You have nothing to do and even the rule is by default set to "Active"
When you are trying to federate (via WS-FED) Office 365 with Okta:
Solution: You can try to federate multiple Office 365 custom domains into a single Okta Office 365 app instance via SWA SSO protocol