Agree...are you saying that support recommended that approach as a fix or  workaround?

Seems odd that something that is clearly not working as expected would be normal. We have just implemented Connect for Outlook and haven't seen this issue before. I will watch for it and perhaps even create a test case. 

Yes support advised it was expected behaviour and said:

“In your case, I would suggest duplicating the event and modifying the duplicated event as opposed to the existing one, as only the events from the Outlook calendar 2 days before the job run date will be retrieved to check for the existence of LMS events in Outlook Calendar.”

Frustrating behaviour for us as we frequently have location changes.

Wow... 

We don’t have an active Outlook Connector over here, but I can see a bunch of example recipes for it. So I think I was able to find the problematic part of the recipe that you’re describing: 

So, without even having a live connection to test, I’m not sure how specific I can be with my advice here. However, given that we know (or ought to know) the actual dates of the events and sessions that need updating, I am truly puzzled that the logic of these recipes does not seem to use that information to filter the search.

But perhaps you could, for example, add an extra step before the current step 2, to get the session from Docebo, and then you’d have the start/end dates you’re looking for? I would certainly hope that you can use these in filtering your search. If it can filter for the past two days, I would have thought it would allow you to filter based on an absolute date range instead…

Anyway. I hope this helps. Please let us know how you get on; our organization is considering Outlook as a second connector, but this limitation would certainly dampen my enthusiasm for it, if it can’t be resolved.

@natashaparish curious why this was not mentioned during onboarding. 

Agree with the comments...this isn't anything we experienced during testing...although Connect is far from perfect.