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2000 Chevy Silverado 1500 5.3liter V8

I have a 2000 Chevy silverado 1500 with about 146,000 miles on it. About a month and half ago. It started delaying going in to Reveser. I fine it does it when it been in Drive for a while and running. Here what happen I go to put in R and I only hear it drop in to gear half way. I go take my foot off the brake and it starts rolling forward. Some time it does it. Its been to my trans place and they found a trans leak and they said that was the cause of it. Its still doing it. I use this truck to pull a 2 horse trailer. I know how to fix this I need a bigger truck to pull the load. But I don’t have the money. It has a rebuild trans in it. What could be causeing this???

You are low on fluid. Keep the fluid level up.

I been checking the fluid and its been fine. Its getting to the point its starting to bother me. Because when I am trying to back up to the trailer it scerws every thnig up…