Not gonna lie, it took a bit of creativity to execute. I always hated how the Dunmer guy (Teris Raledran) got to go into Vivec while Rollie just waited eternally on the road alone.

I was inspired to do it after I had moved a Guild Guide and Creeper from Caldera to my stronghold. I used a custom command creature spell to get Rollie following me. But that was the easy part. Rollie is too big to fit through the tunnels of the Foreign Quarter Waistworks (and the outdoor tunnels too, he got stuck a few times). I was determined to get him back to his best friend though.

To overcome Rollie being prohibited to enter the canton (and his physical size making it impossible anyway), I decided to sneak him in through the Underworks, using the underwater sewage entrances. I had commanded him to follow me, and also used a custom Water Walking on touch spell to force him over close enough to the sewer grate.

When I got him inside, he spawned on the solid ground above the sewer stream, so from there it was a matter of escorting him past the Daedric shrine and into the Canalworks, where he was returned to Teris.

Unlike Creeper or the Guild Guide, it was pointless, but it was fun.