1998 Montero Sport - Oil Pan drain plug question

Is there a trick to getting this thing out? I went to change my oil the other day by myself for the first time, and the plug would not come out, it would loosen, then tighten, then loosen again... all while turning counterclockwise. I then turned clockwise and it did the same thing... tighten, loosen, tighten. Also, now I notice I have a small oil leak after putting it in one of the "tight" positions.

Any help would be appreciated.

Sometimes If overtightend the oil pan bolt threads will strip and the bolt when turned will neither tighten nor loosen. To remove use screw driver and pry between bolt and pan applying constant pressure while turning the bolt in the counter clockwise dirrection. to repair you may need a helicoil installed which involves a tap and installer as well as the helicoil. sometimes once the old bolt is removed get a new bolt and the threads remaining in the oil pan may be sufficient to keep the new bolt tight enough to keep from leaking. You may want to add a hard rubber washer or some sealant to the bolt. be sure not to overtighten more than necessary.

It's a heck of a lesson, I always change my oil instead of a quick & cheap lube service.

Consider using synthic oil, and change every 6-thousand miles.
Check your oil once a month for shortage.