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are you using crickets? Why not let them go in the cage and let your chameleon hunt them down. I never fed one cricket in a cup! If you do decide to go that way, just make sure you don't leave them in there at night. I know they can hide so just put a few in at a time and see if he will eat them. Oh, I see you are using roaches. i never fed those so don't know about them crawling up the screens or on the branches. But the crickets will for sure!
Carol doesnt use roaches cuz shes scaaaarrrreeeeddd!!! hahah only kidding carol, just continuing the teasing from the last thread i'll stop now.
in my opinion though, free ranging is the best way to go for MOST feeders. i like free ranging because it gives the chameleon the chance to fully exercise their tongue. always cup feeding enables the chameleon to dig their face in the cup like a fat kid in a pie eating contest. consistency of cup feeding can potentially, allow the tongue to loose full capability to extend it further distances. because my veiled has been raised to cup feed, i now cup feed some days, and free range others. this way, if for any reason i have to consistently cup feed, she will not forget about it and become discouraged by a giant cup. my multi. on the other hand is a wc, and wont ever cup feed. so for 99% of his feeders, they free range. the only two things he will "cup feed" are wax worms and meal worms, and this is in a very small deli cup.
i would just advise that you do a look over and make sure your cage is "escape-proof" 100% or to the best of its ability. crickets can chew through fiberglass screening for those of you with home made cages, though this hasn't happened to me... yet, i only have one small hole in one of my cages due to my idiocy, a screw, and a drill. crickets will also escape through mesh as small as 1/4'', i have now upgraded my top screen which had 1/4'' aluminum mesh, and switched it to aluminum window screening with hole width wide enough to allow sufficient uvb to come through.
as some of you know or have read, dubias and orangehead roaches are very slow moving bugs. they will be speedy at first, but will slow down and even stop, making it unnoticeable to the chameleon. i think chameleons are kind of like t-rexes' when it comes to movement lol. you kind of have to sit there and wait for the chameleon to eat it up before leaving, because i am pretty sure they will eat through fiberglass screening or material mesh like crickets.
my multi. is a slow eater, like most multituberculatas, they have a much smaller appetite unlike veiled and panther chameleons for example. not only is he a small eater, but he just isn't used to me or other humans yet, even though i've had him 5-6 months now. i dodges when i open the cage or put my hand in there. so i usually have to go on the outside of the cage and kind of bump the roach to make some type of movement.
this technique goes the same for silkworms and hornworms. the will move at first, but after a little bit will die down and be very very slow or just stop moving altogether.
superworms are fine, but again if there is an opening in the cage, if they find it, they will escape. superworms are good free range insect imo, and move quite well. superworms however, sometimes have a very crappy grip to the cage, usually after molting. it could be an insect, that you may have to ensure will be good to stay on the cage. i dont suggest putting superworms on branches, they can easily fall.
that is just a few, sorry for the long post, but i hope it helps.