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2006 Toyota Sienna LE, 190,000 miles
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Hi, 2nd Gen ‘06 FWD Sienna LE with 180k here.

Upon startup in cold weather, my power steering is iffy for the first few minutes. I can hear a belt slipping and squealing around and the power steering cuts in and out. Once the engine gets even a little warmed up, the problem disappears completely.

I’d estimate anything below 35F is where the trouble starts. If it’s warm out and/or warmed up everything works normally. This is my first winter with the van so I don’t know how long the problem has been present.

I did a drain and refill of as much power steering fluid as I could suck out with a turkey baster, then bled the system by turning the steering wheel back and forth with the front end jacked up many times. I didn’t see much improvement if any. Fluid is at the correct level and looks in decent shape.

I was thinking swap the power steering belt out next. I think it’s original...or should I try lubing up the steering column U-joint that many complain about on these forums? I couldn’t locate any threads that gave my temperature sensitive issue, but many talking about the U-joint causing problems.
 

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180K on the original PS belt !?
Absolutely change that sucker out.
Throw a new alternator belt on there too if it's questionable.
Getting the right tension on the PS belt is a pain, you have to simultaneously keep pressure on the pump to maintain tension and tighten up another bolt to secure it in place.
 

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Thank you @sideshowalan . The other accessory belt is relatively new so I think that one’s fine. I am familiar with the agony of the belt tension from doing the timing belt with the help of details on this site.
OP, were you able to get down to the cause of your slipping/squealing belt in the first few minutes of the cold start? I get increasingly the same issue on my 2001 sienna (~250K). All belts were replaced last summer, pump rebuilt with service kit, steering rack swapped out with reman OEM, fluid flushed. Everything worked great until last falls, when cold temperatures had kicked in here in TN. There are no leaks what so ever. Just the steering belt (Gates) slipping over main crank pulley sporadically in the first few minutes when car is cold. Should I turn the steering wheel left and right, it jerks and seizes intermittently, then clears up after a few turns and belt squealing ends. All goes fine, no steering problems until have to start the car cold again.
 

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OP, were you able to get down to the cause of your slipping/squealing belt in the first few minutes of the cold start? I get increasingly the same issue on my 2001 sienna (~250K). All belts were replaced last summer, pump rebuilt with service kit, steering rack swapped out with reman OEM, fluid flushed. Everything worked great until last falls, when cold temperatures had kicked in here in TN. There are no leaks what so ever. Just the steering belt (Gates) slipping over main crank pulley sporadically in the first few minutes when car is cold. Should I turn the steering wheel left and right, it jerks and seizes intermittently, then clears up after a few turns and belt squealing ends. All goes fine, no steering problems until have to start the car cold again.
If there's a tensioner, it typically means the tensioner is bad. Usually just means they adjusted belt tension "by eye" instead of with a tool. Usually, you loosen 2 bolts, pry with a pry bar and then tighten 2 bolts. Anyone should be able to adjust it, even a gas station mechanic. If you had it done at the dealer, I'd complain to them and get them to fix it for free. If it was a trusted mechanic, they'll probably do it for $20 and squeeze you in some afternoon while you're waiting for parts.
 
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