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Don't understand how link between TripIt and expens'd is supposed to work

How and when does the link between TripIt and expens'd work? I have signed into both services and gone through the linking process and both applications seem to believe that they are linked.

I already have a trip successfully created in TripIt, but when I linked to expens'd no expenses seemed to be created in expens'd. How and when to expenses associated with a trip get populated into expens'd? Does this happen when travel bookings are first sent to TripIt? There appears to be no explanation of how all of this works - so I am completely unsure if for future trips things will be nicely automated (like I was expecting) or if there is anything I can do to get expensed related to the trip already in TripIt into expens'd. Can someone help clarify all this for me please?
 
sad I’m confused
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