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I have had them in my castle and then randomly disappear. My tactic now is to just not purchase them on the map until I have a tower high enough level to upgrade. Then again I've brought them with me to a new map and had them vanish on the first day, too.
Using warp portals also counts the distance travelled, so you might have them jump off almost right away after travelling through one.
That I know of, but for me does it take almost half an hour before he jumps off.
When the stars align properly and if he feels like it, he'll jump off.
Alternatively, run from a group of enemies at a time where it would be the least convenient for him to jump off.