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The drillworm comes when you kill bishop alexander
This fight is nigh on impossible on Tactician without a bit of cheap tricks and luck.... EVERY fighter will 2 hit KO and the Bishop and Worm will easily 1 hit KO. What I did was lure the bishop and his melee fighters through the main door while cc'ing their magic armour till you can entangle/freeze. Archer and metamorph will not be able to hit you there. When the worm appears, escape the fight and let the remaining magisters handle it. If you get the position right, the worm will kill all melee fighters but will not be able to hit the rangers, so the fight will be frozen and not reset (or better yet if they manage to kill the worm for you). Then just sneak, hit and run to finish the worm off. It's a bit exploitative but it works if you're really stuck here.
For some reason this page is empty , however the voidwoken drill worm appears just before you leave fort joy. While fighting bishop alexander,(which i recomend you do with just your party and dont request any renforcents from gareth as they will almost defenetily die and are almost no help.) The VoidWoken drillworm will burrow up through the middle of the fight area , when this happens you will get a small diologe between alexander and your party, he will agree to fight the drill worm instead of your party ( this is good time to lay the smackdown on alexander and his goons as they wont fight back as theyre busy) over all this is a rather easy fight and could have been alot harder