Last Wednesday, the Leafs made a trade to clear cap space that sent Timothy Liljegren to the San Jose Sharks. On Friday, in a corresponding move, the Leafs announced that Jani Hakanpaa and Connor Dewar were assigned to the Toronto Marlies on a conditioning stint.
At the time, many were confused by the move as the Marlies played just one game this past weekend and are off until this coming Saturday. Not many understood that the conditioning stint could be three games OR six days, rather than just any three games. On Monday's '32 Thoughts' Elliotte Friedman revealed the Leafs may seek an extension of their conditioning stint.
Should the Leafs ask for an extension on the conditioning stints of Dewar and Hakanpaa, it would give them until November 17th to sort out their roster issues instead of November 11th. Essentially, the Leafs would get an extra week to figure out how and who to remove from their 23-man roster to create the necessary space for Dewar and Hakanpaa to be activated from LTIR.
The status of Calle Jarnkrok is also up in the air. At this point, Jarnkrok has not resumed skating, so perhaps this issue is less pressing, but it's certainly something that the team will need to ponder in the coming weeks as well.