Why does the Oracle try to achieve a different outcome in Neo's iteration of the Matrix?

Question

The Oracle actively contributes to the 6th iteration of the Matrix having a different outcome from the designed one. To some extent, she orchestrates this.

Why does she do that?

From the conversation with Neo in The Matrix Reloaded:

Neo: But why help us?

The Oracle: We're all here to do what we're all here to do. I'm interested in one thing, Neo, the future. And believe me, I know - the only way to get there is together.

Source

Also, from the The Matrix Revolutions:

Neo: Why? What do you want?

Oracle: I want the same thing you want, Neo. And I am willing to go as far as you are to get it.

Neo: The end of the war. Oracle nods Is it going to end?

Oracle: One way, or another.

Source

(I am not going to quote it here, but I think the Architect-Oracle conversation at the end of The Matrix Revolutions suggests that her intentions are genuine)

This seems to imply that the Oracle is unsatisfied with the current state of the machines-humans relationship. To take it even more literally, this seems to imply that the Oracle doubts there can be a safe future (for machines?) if things continue to be as they are.

Why is that? Does she have some specific suspect that the <Matrix + Path of the One> system is not sustainable for the machines and is going to break at some point?

What kind of cooperation ("[...] the only way to get there is together") does she envision?

Or perhaps her intentions are less programmatic (pun unintended) than what we would expect e.g. from the Architect, and her point is that she understood that a peaceful relationship, if possible, is always going to be a more stable solution?

Answer 1

You've quoted or mentioned all the relevant conversations in which the Oracle explains why she helped Neo: she wanted the war to end, and for the humans and machines to finally "get there together" (to the future) in peace.

However, the Oracle was not the only machine that wanted peace -- even the Architect was unsatisfied with the Matrix and The One system:

[The Oracle] stumbled upon a solution whereby nearly 99% of all test subjects accepted the program, as long as they were given a choice, even if they were only aware of the choice at a near unconscious level. While this answer functioned, it was obviously fundamentally flawed, thus creating the otherwise contradictory systemic anomaly, that if left unchecked might threaten the system itself. Ergo those that refused the program, while a minority, if unchecked, would constitute an escalating probability of disaster.

_{The Architect, The Matrix Reloaded (source)}

Not only was the system flawed, but there were real dangers to the machines -- the Matrix was inherently unstable, and if the One couldn't be blackmailed into rebooting the Matrix the machines would be forced to endure "levels of survival [they were] prepared to accept"¹ (the extinction of humanity and lack of that power source for the machines).

The difference between the Architect and the Oracle isn't that the latter wanted peace while the former wanted to maintain the antagonistic system of the Matrix and The One -- it's that the Architect just did not know how to create peace between the machines and humans. He tried to create a peace with his first Matrix -- a symbiotic Paradise Matrix "where none suffered, where everyone would be happy"² while the machines would be able to safely extract power from humans (certainly a vast improvement over the Machine War that occurred in the real world and resulted in the destruction of the sky). Of all the ways in which the machines could have dealt with the humans defeated in the Machine War (e.g., kill them all, put them in a real prison with no simulation, simulate an explicit reward/punishment system for cooperating/resisting, etc.), the machines chose perhaps the most peaceful option they could get to work. While that doesn't prove the Architect was trying to develop a peaceful solution, it does show that peace was a secondary objective (behind the primary objective of the machines' survival) even if the objective of peace was entirely self-serving on the part of the machines (peaceful coexistence with humans is less dangerous than humans constantly trying to resist their imprisonment).

Unfortunately, the Paradise Matrix failed so such a peace was not an option. It failed because

You and I may not be able to see beyond our own choices, but [the Architect] can’t see past any choices.

_{The Oracle, The Matrix Revolutions (source)}

The Matrix and The One system was therefore developed by the Architect and Oracle working together as a replacement for the failed Paradise Matrix. This system introduced some level of human choice (though only at a "near unconscious level") which met the primary objective of ensuring the machines' survival (by using the humans as a power source) and the secondary objective of peace in a limited fashion (by keeping most humans from resisting), though of course it too was flawed since not all humans accepted it. Still, it "functioned" even though everyone from the Architect to the Oracle knew it was flawed.

This system worked for several iterations until Neo's. Neo's iteration exhibited several differences from previous ones: Neo loved Trinity instead of all humanity generically, and Agent Smith had become a virus that could destroy not only the Matrix but also the Machine City. These differences allowed the Oracle to seek a more stable solution: she knew Neo could be encouraged to not return to the Source like The One is supposed to (and that he would actually make that choice because he wanted to save Trinity), and that the consequent failure of the Matrix and the virus Smith would provide Neo with the leverage he needed to strike a deal with the machines to work together to destroy Smith and end the war -- thus ensuring the survival of both the humans and machines, and finally achieving peace.

The Architect did not approve of the Oracle's actions during Neo's iteration because they were risky:

The Architect: You’ve played a very dangerous game.

The Oracle: Change always is.

The Architect: Just how long do you think this peace is going to last?

The Oracle: As long as it can.

The Oracle: What about the others?

The Architect: What others?

The Oracle: The ones that want out.

The Architect: Obviously, they will be freed.

The Oracle: I have your word?

The Architect: What do you think I am? Human?

_{The Matrix Revolutions (source)}

However, the Architect's disapproval of the Oracle's actions doesn't mean he didn't desire a better, more peaceful solution, too. It is simply that, compared to the Oracle, the Architect was more willing to maintain the system of the Matrix and The One only because he couldn't come up with a better solution and didn't understand how to account for human choices. Only the Oracle knew how to account for human choices and predict the future, so she was able to attempt to find a better, more stable (i.e. peaceful) solution on her own.

One can liken the situation to the machines operating with a calculus of maximizing their chance of survival, and the Matrix and The One system was like a local maximum which ensured their survival (but not a truly peaceful coexistence with humanity), whereas the machines' survival and peaceful coexistence with humans was a global maximum that they had not achieved. The path from the local maximum the machines had achieved to the global maximum involved serious risk -- humans started the war in the first place so the machines were understandably reluctant to just stand down and hope the humans would stop resisting (and continue providing power). The Architect -- and probably most, if not all, of the other machines -- could not see a path to reach the global maximum because he/they could not understand how to account for human choices to get there. Only the Oracle could do that.

---

¹The Architect, The Matrix Reloaded

²Agent Smith, The Matrix (source)

Answer 2

The Architect tried to optimize the matrix by minimizing its "anomalies":

Architect: Your life is the sum of a remainder of an unbalanced equation inherent to the programming of the Matrix. You are the eventuality of an anomaly, which, despite my sincerest efforts, I have been unable to eliminate from what is otherwise a harmony of mathematical precision. While it remains a burden assiduously avoided, it is not unexpected, and thus not beyond a measure of control. Which has led you, inexorably… here.

Programs, including the Architect, function in a predictable, logical, and cold way, believing that any problem can be solved with more perfection, and more control. But this has not always worked:

Architect [talking about how his past matrices failed and how the current one was made]: I have since come to understand that the answer eluded me because it required a lesser mind, or perhaps a mind less bound by the parameters of perfection. Thus the answer was stumbled upon by another – an intuitive program, initially created to investigate certain aspects of the human psyche. If I am the father of the matrix, she would undoubtedly be its mother.
Neo: The Oracle.

The Oracle is special, because she has intuition. The Architect thinks this is an aspect of a lesser mind, and of course can not understand what this entails. In reality, she resembles the humans more than any other program. She knows about the repeating cycles of deception (the matrix), hope (escape, neo, zion), betrayal (neo is control) and destruction (of zion). Her intuition tells her this is wrong and cruel.

But, this system is not only cruel to the humans, it is also cruel to the programs. There are some programs that have evolved past cold logic, like Satis parents, who love her like human parents would love their daugther:

Rama-Kandra: No. I don’t mind. The answer is simple. I love my daughter very much. I find her to be the most beautiful thing I’ve ever seen. But where we are from, that is not enough. Every program that is created must have a purpose; if it does not, it is deleted. I went to the Frenchman to save my daughter. You do not understand.

The Oracle knows there is value beyond purpose, she sees the value of love, beauty and true choice. She knows that the machines strive for absolute control is not going to succeed. She wants to help the machines to evolve to understand these things by helping Neo.

_{Source of the quotes: Transcripts on matrixfans.net}

Answer 3

There are 4 ways for the war between man and machine to end:

1. Both sides die
2. All humans die
3. All machines die
4. Peacefull coexistence

The Oracle was for option 4. A lot of machines would have prefered option 2, even at the risk of this ending with option 1. There was a majority for a intermediate solution like the Matrix. For most option 4 was a plain impossibility. Their hatred and inhumanity - created by humanity itself - made coexistence seem impropable.

But the Matrix was also a way for the Oracle and her supporters to prepare the machines for the possiblity of a option 4. To make option 4 appear acceptable. In the end even the Architect (or the source) agrees that option 4 is the best outcome.