It appears that this is working if there are waypoints. Either the behavior has changed or I was mistaken in my original post (leaning towards the latter). Any direct flightplans will not compute a wind component.
The flight yesterday from CYUL to CKK7 had waypoints, but the wind component was 0. When I look back at that plan in my history, it appears simbrief didn’t render the waypoints on the map, likely causing a lack of wind data. Not sure why, I may have made a bad flight plan. A reference image of the generated flight plan:
Here’s the edit screen showing that it understands where the waypoints are, they just didn’t come across in the generated plan for some reason.
So the plan generation issue appears to be some other issue, apologies for the confusion.
I suppose my question now is: Should there be wind data in flight plans that are filed simply as direct to destination?