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Cup feeding is a good way to keep track of how many feeders they are eating. I do this, and then feed maybe 2 or so loose crickets here and there that I can keep an eye on as she eats them. To many loose feeders and you may loose track of where they are in the enclosure. They tend to find somewhere to hide out of sight of the chameleon, which then leads to them just dying off. I also use a feeder run style cup where the bugs are able to climb the back part of it while still remaining trapped. This is good for getting the chams attention.I've been wondering the same thing but have been leaning towards loose insects. I imagine chameleons follow the general animal in captivity rule of foraging/ hunting for food is the best enrichment you can give.
I'm a new keeper and struggling with this right now. I want to cup feed, but he doesn't seem to care about them. I've used a cup as well as the feeders with screens, and the latter the bugs just sit on the screens and he's uninterested. On the flipside, free roaming bugs, I've seen him spot and hunt down in relatively quick order. I think his preference is free-range bugs and the feeders are just going to take time for him to get used to. A battle of wills?
There are health reasons to consider as well. Should you end up with a parasite issue that you have to treat the cham for. These pass and recontaminate from the fecal matter. So if you are free feeding then the cham is only going to want to eat this way. You risk reinfection while treating the cham for the parasite your trying to get rid of because the feeders run through the contaminated fecal left behind.
Also when they are young and you are new to the hobby it is important to know what and how much they are eating. This and their fecals tell you how the cham is doing.
Alot will not feed unless the cup or run is in the proper placement... Almost always this needs to be at basking level so they either look straight at it on the screen or are able to see down into it and nab them while on the basking branch. Loading it with plenty of feeders the first week is important so the cham sees tons of movement and is enticed to use the new method.