Omega Speedmaster only winding about 10-20% of the way

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Your service warranty has already expired. And "so quickly"? It is three years later, after all.

You'll want to send it in again, or to Nesbit's.

By so quickly, I mean the fact that it basically only lasted a year or less. It was serviced in mid 2018, and I stopped wearing it in mid 2019.
I would think/hope that a $750 service on a $4000 watch would get more than one year of use before something breaks. Maybe you are saying this is a typical expectation?

I don't know a lot about watch engineering. What would cause the watch to not wind down properly only when the chronograph is being used like this? Maybe this is a simple fix unlike the broken mainspring I had before?

Also, is it normal for the crown to spin freely in the opposite direction (towards you)? Mine does, and I can't remember if this is normal behaviour or not.
 
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It could be the jumper spring which holds the minute counter wheel in place when the chrono is running. Does the chronograph stop when the large chrono second hand approaches the 12 o'clock point? If so that spring is too tight and needs to be adjusted. It's not a big deal but it is important to get that tension right. It might have been just 'ok' when it was overhauled 3 1/2 years ago but not ok now after three years of wear and degradation of the oils.

Crown moves freely when turned in the CCW direction.

Omega warranties their work for two years, it's way past that point now.
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Someone has to be on the "really bad luck" side of the bell curve. I guess it's your turn this time.