Jamil Viper is the type to have "NO IT CANT BE!" monologue when he realizes he likes someone. He definitely pines hard and will admit his feelings via angry confession.

I don't see anybody talking about this but Jamil L/N! Let Jamil take his s/o's last name!

Its 3 birds with one stone: Jamil is given his freedom on the technicality, he gets to marry the love of his life, and any descendents will also be free on the same technicality. You can't tell me that there hasn't been a single Viper who married into non-servant family and took up said family's occupation. While its a high chance those Vipers were all women, Twisted Wonderland does have a history of gender equality.

This man is the definition of a malewife. It doesn't matter what gender the s/o is, any parent would rejoice at their choice of spouse. You can't tell me TWST doesn't have tech or magic for same-sex couples to have bio children, so the grandchild argument dies there.

Also, wingman Kalim for the win! Maybe he overhears Jamil and his lover discussing the possibility and just goes "YES! I'LL PAY FOR THE WEDDING!"

This dialogue:

Snobbish noble: He can't just leave his master! Its his duty as a Viper!

Kalim: Well he's not a Viper anymore, now is he?!

Bonus: depending on what Najma does with her life, they could potentially wipe the Viper name from the map and guarentee freedom for all descendents.

I've seen some stuff about Jamil taking his s/o’s name but honestly I don't see how that would change much or magically free him.

Like yeah there's that line of his station being “the fate of those born a Viper” or something along those lines. But I would not take it literally enough to assume it's just about the surname. Like, Jamil is working for the Asims because his parents worked for the Asims, and because his parents either chose to have one of their children take up the role of Kalim’s attendant, or because the Asims demanded that of them. (I mean, I'm hoping his parents had at least some choice in the matter, or we really are getting into slavery territory, but I don't remember if that detail has ever been confirmed one way or another). So more of a child following in the footsteps of their parent(s), rather than random luck of the name. So just changing his name would not change that part.

Now, would a free Jamil like the opportunity to make a break with his old life and signify the start of something new with his partner by changing to his partner’s name? He might.

Though I can also see him choosing to keep his surname. Like in a “look at how far Jamil Viper has gotten from where he was” sense. Because to me it doesn't seem that his issue is who he is, the issue is the role he's being forced to play.

Kalim absolutely would need to be held back from organizing a month-long celebration, though.