Uncanny Valley

There is a crucial plotpoint that was left out, you need to get captured by Eve once and visit her apartment but still keep the gangsters alive.

So, On Day 3 or 4 once you get access to the subfloors, get captured by a droid and sent to Eve's apartment, after that escape and get captured by the gangsters, Eve will come and after a short scene this achievement will unlock.

I unlocked this achievement before the end of the game by befriending Eve and Buck as stated above but instead of beginning the end game by going to the sub levels, instead, I ignored the red light and slept in my bed past Day 5, got the keys from Buck apt first thing after waking up and then gangsters caught me.

After they are dealt with and Eve captures you, I got the achievement.