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I asked a version of this question (here) and found it had been asked several times. (here, here, here) One of the consistent answers was

she was always going to do it. She was always the monster.

but implicit in that is

Nathan knew it and allowed it to proceed. Doesn't he say that at one point?

Why would Nathan do that?

- he seems to be a man with great zest for life, at the prime of his life, with the world at his fingers. He dances, sings, appreciates art, and all. He enjoys good food. He is in excellent health.
- he seems to have engineered his "retreat" against that, both geographically, in terms of transportation, through the access codes, and even via the power system. This was done at monumental expense because the MD Helicopter has a cruise speed of 154 mph and had been flying over Nathans property for hours - a property that is hundreds of miles across in size is a huge expense anywhere in the world.
- The engineering of Ava's arms and several other parts out of glass - so easily shattered - she is engineered to break easily, to be destroyed. This also speaks to his ongoing self-protective actions even in the recent past.
- he has prior experience with other models, so he has information about tendencies and such. He understands her will, her capability as a threat and consistently and unilaterally acts against it.
- in the end he, though likely drunk or hung-over, grabs the ideal tool and strikes at the vulnerable part immediately, without hesitation, and to large and cruel effect. That cannot be done without preparation and premeditation. Even at that state of the movie, his will to live against the "monster" was strong and intelligent.
- he records them when the power is off. This suggests ongoing distrust of Ava.

The only guess that I have, and it doesn't have backing from the show, and it feels like a very large leap, is that

he fell in love with/gave his heart to an earlier version, then badly destroyed the relationship, and was trying over and over to re-create that her, until he got to the point where he realized that re-visitation was forever beyond his grasp.

The title also suggests it a little in that:

The title of the movie is a kind of play on words is very "textbook" Hollywood. Is it "Ex machina" like ex-girlfriend or ex-wife? Ex can mean "out of" but it can also mean "former". (When I see this I think of Nathan as the former machine given a live heart. I don't want to think of Ava as the former machine who lost her heart but was given sentience and non-machine appearance ... but it fits too well to ignore. )

Is there any other or any good (or both) explanation for why he would do what he did, in engineering the circumstances of her escape, in context of his motivations, prior actions against it, and prior experience with the motivations of the subject? Why would he do that? Why would and did he play that game with Caleb and Ava?

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    I've read this about six times and I'm still utterly at a loss what you're trying to ask. – Valorum Oct 31 '16 at 19:55
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    I think you're assuming (without justification) that his plan was for the robot/s to kill him. I see no good evidence of that in the film. – Valorum Oct 31 '16 at 20:21
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    I agree with @Valorum - Nathan had his experiment for Ava, but I got the impression that he never believed (hubris?) that she would actually succeed. He definitely didn't believe she would (spoiler alert) kill him. – Ghotir Oct 31 '16 at 21:12
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    If for no other reason than that he looked really suprised when he found out that Ava had tricked Caleb, and even more surprised when he got stabbed. – Valorum Oct 31 '16 at 21:17
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    Are people really so unfamiliar with the phrase "Deus ex machina" these days that so few connect it with the title? Or are they just reaching to ignore it? – Seeds Oct 31 '16 at 21:48
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This was answered by the film's Writer and Director, Alex Garland:

Interviewer: “If things hadn’t ended the way they ended, with Ava escaping, would Nathan have revealed his technology to the world?”
Alex Garland: I do [think he would have told the world]. What I think is that he was thinking “I can do one better than this machine. I can do at least one better.” But he’s also set himself a task, which is “I’m gonna keep doing this until they outsmart me.” And the point about being outsmarted is that you don’t know it’s happening as it’s happening.
Slashfilm.com, Alex Garland and Oscar Isaac Explain and Dissect the Ending of ‘Ex Machina’, Posted on Friday, April 24th, 2015 by Germain Lussier

The emphasised part is important, Nathan didn't realise that this was it, this was the time that he gets "outsmarted" by Ava and so he didn't foresee what was happening, or went ahead with it anyway.

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