Although I would usually suggest that the casual bike mechanic does not need high end tools, I advise you to spend the money to buy a good chain tool. A balky chain will quickly break the pin of a cheap chain tool and since cheap chain tools do not have replaceable pins, you will be driving back to the discount store for another one. Save yourself the headache and get a tool with replaceable pin.
The photo above shows a Park CT-3 chain tool. This heavy duty tool works with 3/16 and 1/8 chain. If you can get a good used one or afford a new one, buy it. This is a lifetime tool.
To break a chain, place it into the bottom pin shelf of the tool. Hold it in with your thumb and screw the pin down until it holds the chain in place. Now visually inspect that the tool pin is correctly centered on the chain pin. If it's off to one side, back off and try again.
If everything is lined up correctly, go ahead and start cranking the chain tool down. Most times there will be moderate resistance as the peening on the chain is pushed in and then the pin can be cranked easily through the chain.
If you are planning to reassemble the chain with the old pin (more on this below), you must stop pushing the pin when it reaches the last plate. As you start to get close, remove the chain from the tool and gently try to pull apart. If the chain pin is still too deep, put the chain back in and crank it another turn and remove and try again. If you push the pin all the way out, you will not get it back in there.
A note about reassembling chain: This is not advisable for high stress use. Since the peening is removed from the pin, a chain under a lot of stress can pull the side plate over and off of the chain pin, breaking the chain. Ok for beach cruisers, not OK for single speed mountain bikes. A good quality quicklink is much safer for heavy use.
Now that the chain is reassembled, the reassembled link will be tight. Move the chain up to the loosening shelf. Get everything straight and then screw the chain pin in about 1/4 if a turn. Now the link will have enough slack to work smoothly.
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