What you're doing is pretty complicated, and best handled by a pro at a salon. The reasons for this are: Putting brown dye over highlights can be done, but it depends how light the highlights are and what the base of the brown dye is if it will work well. It might work great, but If the highlights are white or pale yellow, you could run into trouble with the base of the dye coming out a funny color on those strands. Keeping it separate and just doing the roots brown, then highlighting roots only on your highlighted strands would be better for your hair, but would be super hard to do and will likely result in uneven spots.
So, just dying it brown then rehighlighting may work, and would be the easiest way, but definitely try a test strand for the brown dye on a highlight to make sure it won't come out a funny color. Redoing your highlights will be damaging over time since some of the hair will be highlighted repeatedly, and more and more of it will eventually have been highlighted. It may be easier in the long run if you decide to be only one whole-head color, or just have highlights over your natural color since you are worried about hair health. Either of those ways you could just do "roots only" each time.
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