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Some Troy Bilt Tillers were designed with a manual "free-wheel". If yours is a Tuffy (and maybe a Junior), you have to pull pins out of the wheels to move the tiller without starting it. The larger tillers, Pony's and Horses, had a lever to shift to release the wheels.
The recommended lube for a Troy Bilt transmission is 140 Gear Lube. It's tough to find. If you use lighter oil, the trans seals will likely start to leak.
You likely have a clutch problem, never saw one that a simple adjustment would fix. I'd take off the tiller (there are two bolts that hold the tiller portion to the transmission, and check to make sure the clutch is sliding in and out. My hunch is either the lever is loose on the shaft or the allen-head little bolt that they use to shift the clutch has come out. Be sure to grease the clutch while you're in there.
This should be covered in your owners manual. Shame on them if they didn't mention this.
1.on each wheel pull pin in center of hub
2.push wheel closer to motor.
3.put pin back in to axle but not though hub
4.do the same steps to other wheel
now you can push tiller
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