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I have a 2000, F250, 7.3, automatic with 220,500 miles. When I purchased my truck used in 2008 (173,000 miles), i had the transmission rebulit by a ford dealership. Okay my problem is now that the weather is cooler here in Texas, when I back out of my parking spot in the morning, it takes several seconds for my truck to engage into drive. The rest of the day it works fine, only first thing in the morning. No problems driving (shifting) during the day.
The fluid, when cold, is slightly thicker, causing it to take longer to pressurize everything. Once the fluid warms, it thins a bit and flows better and pressurizes everything faster.
Most likely you have some pump wear, a slight restriction in a critical passage, or, perhaps, a small internal leak that's bleeding off internal pressure until a seal heats and expands to seal the leak.
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