Recently I ran in to smiling Larry while traveling. I have two points in cap collector and local leader so I asked him to come back to my settlement. I sent him to red rocket truck stop and my population went up by one so I assumed it worked. The population was 7 before and went to 8 right after asking him. It is connected by supply lines to other settlements 15+ which I think met the 20 population requirement.

I fast travelled to red rocket truck stop and waited 4 days but he did not appear. Since then I have continued playing and I'm estimating 10+ in game days have passed and I still haven't seen him. I've gathered settlers by bell and two are unaccounted for one I'm fairly certain is my provisioner, the other I'm assuming is Larry.

I am also missing Smiling Larry after directing him home.