the crimper has to match the connector
the first tool looks like an Amp Superchamp knock off. the real Amp tool used on Amp PIDG terminals works fine. other combinations... mebby not.
the second tool is a Stakon type. maybe more forgiving. it wil also work better with the parts it was designed to be used with
PS with the wrong tool you can be loose, or over crimp the wire and make the connection brittle