He should prepare first

With a sigh, Cailean approached and open his bag that is strapped to his horse and perused it to see what he has again. Aside from tents and bedrolls, Cailean has several rations for multiple travels, a crowbar and a spare med kit.

Cailean simply took the crowbar just to be safe.

He has his rope, a ration, waterskin, even lantern and tinderbox. So Cailean isn't in danger, but having something like a crowbar wouldn't hurt.

With that, Cailean approached the hill...