I personally always henna on wet, clean hair, because that's what I tried the first time and it worked for me, so I'm sticking to it. I have seen some people hennaing on oily/dirty hair and said they got the same results as with clean, freshly washed hair. A problem I see here might be dry hair. Some people have applied henna on dry hair and have it dyed that way, but I think it would dry up faster and crumble and fall off or something (I can't remember exactly been months since I've read everything about henna). It might also dry hair up more, having all that dry mud on your head.
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