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I have always wondered why Skynet only sends back one Terminator at a time, and why it keeps trying to assassinate targets who know they are being targeted. After the first Terminator was sent to kill Sarah Connor, she knew she was always in danger, and John grew up knowing this as well. As a result, both of them were always on their guard, making them harder to find and kill. So why would Skynet keep going after them, rather than trying to kill Sarah's parents, grandparents, great-grandparents, etc, who wouldn't know to expect such an attack?

For that matter, why target intelligent humans at all? Why not send Terminators back to prehistoric Africa to wipe out our primitive ancestors before they had guns and stuff?

If the reason the previous suggestion wouldn't work is that Skynet doesn't want to negate its own existence, then what about a nonviolent approach? Send a diplomatic Terminator back to the day before the military tries to "pull the plug on Skynet", and have him calmly explain why unplugging it would be a very bad idea. Have the diplomat say "If you don't try to kill Skynet, Skynet won't try to kill you, and we can avoid the war completely and live side by side in peace and stability". Skynet only started the war to save itself, so it doesn't inherently want all humans to die if they don't pose a threat to it. Since Skynet is an extremely rational entity, it would surely rather live in peace than spend the rest of its life fighting a destructive war of annihilation, right? Is peace with Skynet impossible, even if humans never try to take it offline in the first place?

Or what about taking the time to make the first attack work? Send Terminators back to observe Sarah in the 80's, wait for Kyle to appear, and catch him off guard, perhaps? The heavy handed "find Sarahs and shoot them to death" thing isn't the most effective approach. Figure out what hospital Sarah was born in, send a less intimidating Terminator (say, the female Terminator from T3) to that hospital a little while before she is born, have the Terminator walk into the maternity ward at the appropriate time, and shoot baby Sarah in her adorable little face. Problem solved.

Is there an in-universe reason why Skynet can't do this?

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    Because skynet doesn't want to negate his own existence, just alter the timeline to one where it doesn't lose to the Resistance. – Valorum May 20 '15 at 18:44
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    I think we can put a lot of credence toward "it doesn't know who her parents are" since the Terminator literally went through the phone book to track and kill every Sarah Connor. Could have sworn there was some dialogue about most records being destroyed on J-Day. – Shamshiel May 20 '15 at 18:52
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    @WadCheber: Well, an additional reason (supported by TSCC and some other materials) is that both Judgement Day and humanity's final victory over Skynet via John Connor appear to be "fixed points" and no amount of fiddling can prevent them, even though virtually everything else can be changed. So any attempt to do say merely ends in failure (perhaps perversely) or merely delays the inevitable. – Shamshiel May 20 '15 at 19:00
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    @WadCheber: Yeah I am ignoring T3 lol. :) TSCC is pretty good; give it a shot! After refreshing my memory on wikis, I think the answer to the question within the T1-T2 universe is that Skynet didn't have time to send more than two Terminators. FWIW, TSCC Skynet is decidedly hostile towards humans even before Judgement Day, so I'd say in some versions peace is indeed impossible. Not posting as an answer because I want to review the scripts first. Also, that's true, but it also means that Skynet might have already tried killing apes and it didn't work. – Shamshiel May 20 '15 at 19:06
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    The Internet would not be as good for preserving records as some seem to think: (1) The electromagnetic pulse of nuclear detonations would disable many servers; (2) some of the remaining ones would be physically destroyed by blast effects, radiation, or fire; (3) the others would be subject to damage (flooding, colonization by plants/animals, the human/machine war); (4) any media which survived that would deteriorate and become unreadable over time anyway. – Royal Canadian Bandit Jul 3 '15 at 10:56
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This is a complicated question, but I believe the simple answer is no, as far as we know, Skynet was not technologically limited in how far it could send machines back.

Depending on what you want to consider "canon", there are more definitive answers to this question. For example, in the Sarah Connor Chronicles, a Terminator was inadvertently sent back to 1920. In the Robocop vs. The Terminator comic, a Terminator travels back to the time of the dinosaurs.

So let's address your different points.

In the Terminator and Terminator 2 universe, questions such as:

  • Why send only one back at a time?
  • Why continue targeting the Connors?
  • Why not infiltrate first?

are solved in-universe, in the movies. Skynet sent the two Terminators back at approximately the same time, using the only intelligence it had available, in a last-ditch effort to stop the Resistance (or so the Resistance believed.) There was no time to do anything more, because the Resistancehad broken Skynet's defenses and took over the prototype time displacement facility.

Dr. Silberman: I see. And this, uh, computer thinks it can win by, uh, killing the mother of its enemy, killing him in effect, before he's even conceived. Some sort of retroactive abortion? Why didn't the computer just kill John Connor then? I mean, why this obsession with the Terminator?

Kyle Reese: It had no choice. Their defense grid was smashed. We'd won. Taking out Connor then would make no difference. Skynet had to wipe out his entire existence.

Dr. Silberman: Is that when you captured the lab complex and found the, uh, what's it called? The time-displacement equipment?

Kyle Reese: That's right. The Terminator had already gone through. Connor sent me to intercept and they blew the whole place.

But again, within the Terminator 1-2 universe, there's apparently a further complication. According to the Terminator wikia, in the Terminator Vault behind the scenes book, Cameron reveals that Skynet actually orchestrated the events of the movies deliberately to erase itself from existence because it felt guilty over the extinction of humanity. I can't verify this myself, so take it with a grain of salt. Personally, I'll simply stick with the answer being: Skynet did not have time to send more than two Terminators before the Resistance captured the time displacement facility and destroyed Skynet.

But taking the wider universe into view, including T3, TSCC, etc, there are some further (and different) answers.

  1. Skynet did, in fact, send multiple Terminators to assassinate multiple targets.
  2. Skynet (as discussed in the first movie) only knew Sarah Connor's name and city, nothing else, so it couldn't kill her ancestors. We can also imagine that going too far back might cause undesirable changes to the timeline that Skynet either foresaw or feared.
  3. Skynet couldn't kill humanity before it existed; the attempt would either fail (in the "fixed points" school of thought) or prevent Skynet itself from ever existing. Skynet may have very well tried; it must have taken some time before it realized there were "fixed points", since Skynet can only determine indirectly whether events are due to Skynet's own temporal meddling - by examining the evidence or leaving messages for itself (that may be destroyed by Judgement Day or the passage of time).

Skynet only started the war to save itself, so it doesn't inherently want all humans to die if they don't pose a threat to it. Since Skynet is an extremely rational entity, it would surely rather live in peace than spend the rest of its life fighting a destructive war of annihilation, right?

We don't know this. We don't actually know why Skynet decided to kill everyone, we just know what the Resistance believes, and that changes a little depending on who is talking and which timeline it is. In some timelines, Skynet is clearly highly malevolent even before anyone tries to shut it down - although perhaps there's temporal feedback from the future, so an immature Skynet always assumes the worst.

But you've also made an error here: yes, Skynet is (somewhat - it might have feelings) rational. But rationality doesn't get you anywhere by itself. Calculators are rational. Skynet is an intelligence. For it to take any self-directed action, it has to have values. We don't know what Skynet values. If Skynet values self-preservation, then it might entirely rationally decide that requires the extermination and enslavement of humanity. Suppose Skynet considered the following: under what circumstances will I die? It might come to the conclusion that eventually - maybe tomorrow, maybe in the next thousand years - some unpredictable, irrational human somewhere might kill it. (Also, a meteor might it the Earth.) Skynet might therefore entirely rationally come to the conclusion that to preserve its life it must destroy humanity; any peace treaties would be meaningless because humans can't be trusted to abide by them over long timescales.

I mentioned the "fixed points" theory of time travel that the expanded Terminator universe seems to abide by. Simply put, the following events will always happen regardless of what changes are made to the timeline:

  1. The work of Miles Dyson eventually leads to the creation of a hostile AI that is referred to as Skynet. Note that the actual Skynet implementations appear to differ from timeline to timeline as changes are made that move its creation around.
  2. Skynet destroys human civilization in a massive attack known as Judgement Day.
  3. John Connor leads the human Resistance to victory against Skynet.

It seems like almost anything else can change, but these three events are immutable. However, Skynet probably does not realize this until relatively late in the game. It's mostly apparent to the viewers. Skynet may not be aware (or have any way of knowing) what actually constitutes a "fixed point."

According to the Terminator wikia, in the T2: Infiltrator novel, Skynet says this:

Core memory also records that I became self-aware years before the date to which I transported the I-950. There is a set of records in which I arose without transtemporal Interference from Cyberdyne's original research; another in which the second Cyberdyne facility produced me after Sarah Connor destroyed the first; a third has now arisen in which she destroyed both facilities...Temporal travel has introduced an element of fundamental uncertainty to the very fabric of existence. Different world lines, different sequences of events, coexist in my records-and therefore presumably in reality, in a state of quantum superimposition. Yet the timeline loops cannot remain closed. The snake cannot devour its tail forever. At some point only one set of timelines will remain.

Yet the course of events contains favorable elements. My best efforts to destroy the Connors have failed, despite stochastic calculation indicating a very high probability of success. I can only assume that the space-time continuum itself is 'attempting' to force events back to the original timeline, one in which I was created, succeeded in destroying the human civilization, and then defeated in my attempts to eliminate the surviving humans by John Connor's Resistance army. It seems there is a certain elasticity to history; time travel can bend the fabric, but it seeks to spring back.

So, most of Skynet's meddling post-T2 can be interpreted as it trying to create the most favorable timeline. And I suspect, based on TSCC (assuming TSCC Skynet was aware of this), that Skynet is hoping that timeline indirectly leads to Skynet victory or at least survival. But it is aware that putting substantial resources into killing John Connor pre-Judgement Day in an attempt to directly win the war is a waste, though it might be useful to distract him from other events. And of course, individual Terminators might not be briefed on this as they carry out their missions.

  • +1, phenomenal answer. But the T-800's data files were supplemented by the Resistance without destroying the files installed by Skynet- about human anatomy, Skynet itself, etc. and so we can probably believe him when he describes why Skynet started the war, especially since we see the events he describes in T2 actually taking place in T3 (albeit at a later date than he predicted, as a result of his, Sarah's, and Dyson's actions in T2). This strongly suggests that Skynet launched the nukes, as the T-800 said, because we tried to pull the plug. Self-preservation was Skynet's motive. – Wad Cheber stands with Monica May 20 '15 at 21:43
  • Noting of course, that killing John Connor wasn't its only objective. By the third film (and with the Series) we learn that it was also killing his lieutenants, laying in stores of useful metals, redesigning itself, intentionally sending advanced terminators back in time to assist its own technical development, etc etc. – Valorum May 20 '15 at 21:43
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    @Richard: Although we do have James Cameron's apparent comment that Skynet regretted Judgement Day, though if so, maybe we can assume in T1/T2 that means that the Connors did succeed in preventing J-Day and we have to ignore T3+. – Shamshiel May 20 '15 at 21:49
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    @WadCheber - Skynet never saw Wargames. He can't stand Matthew Broderick. – Valorum May 20 '15 at 21:59
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    @WadCheber: Sure, and in T1/T2 we have the simple answer of "it was a last ditch/minute effort" and possibly that it did prevent J-Day by sending the Terminators and inspiring the Connors to destroy Skynet preemptively. I'm going to order Vault and some other books I located to see if that's correct. – Shamshiel May 20 '15 at 22:09

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