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It sounds like your rear wheel may be misaligned and/or the belt is misadjusted.

When the motor's pulling, the belt moves to and rubs against one side of the pulley but when the bike is pushing the motor (decelerating) the belt rubs against the other side of the pulley.

You can see this for yourself by turning the rear wheel when the bike is on a lift.

Rainwater may be just the thing to cause the rubber belt to squeak when rubbing against the pulley.

The primary chaincase is sealed and therefore unaffected by rain.

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Q: Why does my 1994 Heritage Softail squeal from the primary when I ride in the rain it only does this when I let off the throttle?
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