Maybe I'm in the minority but I thought last night's episode was terrible. Reese negotiating with the machine just doesn't make any sense. In the context of the show, I would even accept that Finch put in a failsafe to track himself and that the machine could search for him if he hadn't logged in in a while and the machine could notify Reese in some way. It would tell Reese either where Finch was or was last seen. But for the machine to be swayed by Reese's emotional appeals and then dribble out clues to the background of Root instead of just saying where Finch is/was makes no sense at all.
I won't even get into the fact that no casino in the world would let Finch win hundreds of thousands of dollars while obviously getting clues from a buzzing cell phone.
Reese's appeals may have been couched emotionally (he's my friend), but the machine interpreted it logically: If you want me to continue the work, you have to do something for me. Prid pro quo.
It appears that Finch purposely lost at the end in the scene shown, when he realized that he was drawing unwelcome attention. Still, the cell phone prompts was a stretch.