Sounds simple, but often overlooked. Ensure the oil ports on your bar are cleaned out so that the oil can get into the bar rails. I usually use a small pointed tip pocket knife to clean the gunk out of the rails starting at the tip first bringing it toward the heel of the bar (so it doesn't get gunk in the sprocket tip). You'll see some small holes in the sides of the bar on either side near the bar stud groove. Make sure the hole on the powerhead side of the bar is cleaned out. To ensure the oiler is actually functioning (or not), take the bar and chain off and run the engine (with the chain brake off) for a little bit. If it's oiling, you'll have a lot of bar lube coming from the pump. If you don't see any oil coming out, then you have another issue.
Have had multiple Huskies at home and at work of every shape and size and have never had an oiler not function, but anything is possible. Good luck.