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Q: engine roars when started, brakes sqeek in the rain on 2001 Toyota Tundra

The trucks engine roars for a minute or two when started then settles down is this a sign of engine trouble ? The brakes squeek when it rains and feels like they have no connection ,I need to pump them up to get the brakes to stop squeeking and feel connected, do they need to be replaced?
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the engine roaring may be from the clutch fan in front of the motor. have it checked to verify.

the brake squeal comes from material noise, the warners hitting the rotor or glazed rotors. get them checked as well.

The roaring is probably the fan clutch getting into the mood to work properly. Usually they are a viscous fluid drive and the fluid settles into the lower part of the unit and takes a few minutes to warm up an distribute itself properly for the fan clutch to drive smoothly. This is pretty much normal, especially in a truck which would use a fairly heavy duty system. My Dodge Diesel does this too.
Brake squeak is not a concern in itself but that the brakes don't seem to work is a big safety concern. I recommend you find a toyota specialist and get him to give you an opinion while looking at the brakes, not just over the phone.
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