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Suppose a transgender male (born female) who's undergone bottom surgery and tattooing to make his genitalia look more masculine decided to convert to Orthodox Judaism.

Would such a person be required to undergo a Hatafas Dam Bris as part of their conversion process?

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    If there's no need for it Halakhically or medically, then doing so would probably be prohibited since it is forbidden to wound oneself. Though that might not apply while they are a non-jew.
    – Double AA ♦
    Commented May 23, 2019 at 14:19

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Here is an excerpt from Encyclopedia Halachit Refuit from Dr. Avraham Steinberg.

EHR

Translation (my own): A women who underwent surgery to appear like a man, even if they formed for her a male limb, there is no obligation to do a bris on this limb, even if it is formed from her natural clitoris.

In regards to a non-jewish woman that underwent gender reassignment surgery to become a man, it is not appropriate to accept them as a convert.

It appears that there is also no need to do hatafas dam bris, otherwise he would have mentioned it.

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