Sometimes it seems like the last person to do an oil change must have used their full weight on a breaker bar to tighten the drain plug.
Luckily, this time the drain plug didn’t get stripped out, but the crush washer showed just how overtightened this was. These start out completely flat, and should stay pretty flat, but this one was extremely misshapen by getting tightened too much. Most manufacturers recommend replacing the washer every time you do an oil change. Sometimes I don’t if they’re not readily available, unless it was crushed this badly. Drain plugs don’t need to be tightened nearly this much.
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-Dan