Why is the oil Dip stick easy to remove but hard to put back in?

Hello, times like these I suggest visiting a repair facility near you to show them and get an opinion. For something like this, a consultant should be able to take a moment and help you without having to generate a repair order or charge you anything. At the same time, you might be able to create a valued relationship with a trusted technician or shop. Good luck! https://repairpal.com/repair-shops/toyota-repair-and-service-in-tucson-arizona

Its possible the dip stick tune is pinched. This would make it hard to remove, install and it could wipe the oil clean. Take a good look at the tube and look for bends or see if its crushed. Alex

Use a little finesse - don't force it .. It's nothing wrong - just inherent to the 22RE 4 cyl. Insert the dip stick into the tube in same position it came out. I'm assuming it's the 4 cyl. engine in the truck - just by your question.