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My 1994 E350 Clubwagon 175,000 miles 5.8 E4OD slips in and out of gear when cold, below about 35 degrees (stops slipping after warmup 5 minutes or 5 miles). It has also developed a shudder when shift 1-2 & 2-3. Trans was overhauled and upgraded about 50,000 miles back. We use this van for hauling newspapers for bulk deliveries so we haul anywhere from 1,000 to 6,000 pounds everyday.
It sounds to me like you have an internal pressure leak. I don't know the quality of your overhaul but it sounds exactly like the lip seals have gotten hard. Typically from age and heat.
With 50K on an overhaul on a 175k transmission, it is likely a worn out boost valve in the pump, or worn bushings.
The cold slipping and shudder are symptoms of that kind of problem. You could try changing the fluid and putting in a bottle of Lucas but it likely won't help for long if at all.
50K miles on an overhaul, especially in a truck that's worked that hard, isn't unreasonable at all. When I owned my shops, we only offered 12 month/12,000 mile warranties on commercial trucks. The trucks we did for CSX (rail road trucks), we did pretty much annually. But then these trucks were worked REALLY hard. They run three shifts a day and when on the tracks, never get shut off.
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