Last night while I was playing I came across a terminal I couldnt hack. I have been traveling with Valentine and I hear him across the room say "If you want me to take a look at that terminal...." Being that he is a synth, and quick check online confirms he should be able to hack terminals. So I click on him to give him directions to hack the terminal but no matter what I did I could not get him to do it. click on him, go to the terminal, click on the terminal and I get the message that its too tough for me to hack. I tried a lower terminal and instead of him hacking it I just sit down and go into hack mode. What gives? I've gotten Cait to pick locks for me before but for the life of me cant get him to do it. The only thing I can think is that both terminals were in the same building that I happened to come across that I assume plays into his back story at some point.

Same way you get Cait to pick locks, you do have to be far enough away from the terminal so that the game doesn't think you're trying to use it instead though.

i was thinking that might be in. In both cases the terminals were at a desk facing a wall so I couldnt get far enough away from it without being behind it

Sometimes you have to stand on something at a weird angle to get the distance you need. It feels awkward as it sounds.