I 've had a terrible mistake. I will own it and I should have been more careful and double checked, so I will relate my journey so that hopefully metamask is a bit better regarding this: please, when searching addresses to send funds, include the owned ones that have been given a name.
I was transferring funds between my accounts, doing some “SecOps”, cold storage, etc. I named one of my account (lets call it A) in a way that had partially shared the name with an old bookmarked address that was not under my control and that I had totally forgotten (lets ca it B). So I wanted to send funds to A, but when I searched for the name of it in the search bar, only B (not under my control) appeared. So I did not double check and I ended up sending my funds to B because its name started the same way as A.
If both had appeared, then probably I would have said to my self wtf, why do I have two accounts that have similar names, and I would have sent to the correct one. Lesson learnt anyway, got too comfy around and this is my first fat finger… never again.
But for the sake of idiot people like me, I think this should be addressed. Please include named accounts in the bookmarks when sending funds.