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I'm having this issue also. Before I patched both workshop framework, sim settlements and conquerer, he wasn't going to the outpost I sent him to but now he won't talk to me.
In my gameplay Jammer stops talking after I conquered outpost and a farm, and we got rid of attacking gunners. To be more correct I can say he talked once after that, but I told him I am going to get to settlement attacks later, and now he just ignores me and wanders aimlessly in Sunshine Tidings. Workshop and SS are updated to latest version.