727 Torqueflight Won't Engage

Update on the issues I was having. Ran the car again let it warm up and rechecked fluid level. It was very low. Well looks like I have a deep aftermarket chrome pan with "727" embroidered on the bottom. I didn't know this wasnt stock since I've never worked with one of these trans. Obviously more fluid needed to get proper level. Rechecked in neutral and went through the gears again and started to engage as normal. Went back and forth in the garage with no issues and went around the block with no issues or hard shifts. Looks to be good to go. Thanks again to everyone who commented.