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I am a novice wrench, but am willing to give everything a try. In this case I was installing a new Shimano 9-speed drivetrain - Cranks, chain and cassette. The chain and cassette were new and the cranks were used (ebay purchase) but in much better condition than the cranks on my bike.

I installed everything, the cassette and the chain were good, but the crank was not aligned with the front derailleur. I couldn'r figure it out, so I brought to my LBS. They said that I just hadn't torqued down the crank enough, it needed another half-turn. Besides that everything looked fine.

This morning I went for a ride and while clipping in the non-drive crank swung free. I put it up on the stand tightened it and tried again, and again it swung free. I removed it, it looks like the teeth sheared. So after all of this here is my question.

When I installed the crank, I left the ring bolt in place, positioned the crank on the bottom bracket and tightened it using a crank wrench. Should I have removed the ring bolt first positioned the crank and then inserted the ring bolt?
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