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Hey guys, I needed some advise regarding my British passport application, I have fully naturalised and requested my passport

now the complicated stuff, I am a trans woman originally from Italy, I have changed all my documents including NHS (so I am F for the UK in every way) details. My naturalisation certificate is in my legal female name.

Unfortunately in Italy, things are super archaic still, and I can't change my name until I had my full gender reassignment and still then, I'd have to go through the Italian courts to get my name aligned, and gender marker change. it is quite a hefty and expensive process, but more than anything, still a long reach for me. I am looking to get sex reassignment in September, meaning It will take another year and something to even sort my legal docs in Italy (that I will have somehow prove in Italy as I have transitioned in UK)

I did leave a cover letter explaining the situation and the difficulty of having the gender change in Italy, tho it isn't impossible, also, I attached the letters from my gender psychiatrists to confirm my gender dysphoria and that I am living as my true self and this is it.

Do you guys think they will find problems to issue me the British passport in my correct name and gender? any tips on this regard.
I even stated I wouldn't care so much about a notation about my having an Italian passport with such and such number, as long as I have a correct document that match everything about me because having my old one, it is extremely awkward , most people don't believe me its me because it looks like a distant brother of mine, and yeah it's just very difficult.

any tips are highly appreciated

Your situation is unique but I believe HMPO wont issue you a Passport if you hold an existing uncancelled Passport from another Country. So, you will have to cancel/renounce your Italian Passport/Citizenship [Not sure if this is possible] and then apply with your Naturalization certificate and get your British Passport.

I've heard people being able to have a different surname because they put on a case that their own country (like Germany, but similarly Italy too), name changes are difficult to obtain.
I mean, my situation with gender change is even more complicated than that.

I am hoping that somehow I am able to sort this, I did see that they do allow it for gender change If the country of origin doesn't allow it, I mean Italy does, but the process is way more thorough and complicated and less fluid than here in the UK. annoyingly so.

I would be okay with canceling my Italian passport, but renouncing Italian citizenship is not an option (because re-obtaining it is only allowed in very specific circumstances)