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I know Halo of Flies counts, but does Pretty Fly (pill or slot machine) count towards the transformation?

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No, the pretty fly through pill or slot machine does not count towards the transformation.

In some runs, I've got more than 3 pretty fly pills, but 1) I did not transform and 2) I still had to get 3 items required to transform.

Only the items listed here will transform you into lord of the flies.

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