Squealing usually means rubber rubbing where it shouldn't (a slipping belt) or a brake pad wear indicator scraping a rotor. Both are common, both are usually cheap - but ignoring them turns a $30 fix into a $300 one.
High-pitched squeal at startup or when AC kicks on. Cracks visible on the belt back. A $30 belt and 30 minutes of work for most cars.
A continuous squeal that goes away when you apply the brakes is the metal wear tab telling you to replace pads. Different pitch than the brake-applied grind.
Squeal that does not go away with belt replacement. A bearing in an idler or tensioner pulley is failing. Check by spinning each pulley by hand.
Squeal only with AC on points to a slipping AC clutch or seized compressor. Costly but isolated to the AC system.
Squeal that gets worse when you turn the wheel sharply, often paired with low fluid or whining. Can be belt slip on the pump pulley.
A worn serpentine belt can break suddenly and leave you stranded with no power steering, no alternator, and no water pump (depending on routing). A failing tensioner can throw the belt off entirely.
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Days to a few weeks. Belts that are squealing are nearing failure. Replace within a few weeks - it is a 30-60 minute job on most cars.
Cold rubber is stiffer and grips less, so a marginal belt slips at startup and quiets as it warms. Replace it before it stops working entirely.
Not always. The squeal is just the wear indicator. If you catch it early, pads only - $150-$300. Wait until it grinds and you also need rotors - $300-$700.
The AC compressor adds load to the belt. A worn or loose belt slips momentarily under that extra drag. Belt replacement usually fixes it - bad AC clutch is a smaller minority of cases.
Never on belts or brakes. WD-40 makes belts slip more and contaminates brake friction surfaces. The fix is replacement, not lubrication.