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Originally Posted by BrianG
It sounds like you aren't getting the connector hot enough to melt the solder that is inside the little socket (where the wire would sit). Once all the solder is in liquid form, the wire should slide right in.
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Yep, I agree.
The other thing is to make sure that once the wire is inserted into the hot solder in the connector, hold the iron on it long enough to wick the solder onto the wire.