If its any consolation my 06 magnet looked the same after I changed the oil, my filler plug had never been touched since factory yellow paint marked. Swarf wasn't quite as big as in your second pic but a magnet covered in Swarf like yours none the less. if your second gear change was playing up before then don't put Redline in it is what I say!
I had zero gear change issues until I put Redline in and now my 1st to second change is a constant fucking pig plain and simple!
I have never even bothered to change oil in a gearbox before I got a TJ and let me tell you Redline is a fully synthetic "performance oil" and in my opinion way too thin for every day use in manual TJ,s but more suited to high performance motorcycles!
Performance oils are not needed or warranted else Mopar would have been performance rated thin shit!