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Webmind is cheerful, inquisitive, and has (once he's advanced far enough to recognize what that is) a near-endless faith in the good of the human race. He outright describes himself as "not disposed to guile". You could also accurately say he's a being of literally endless curiosity and energy (as both cracking Caitlin's email password to learn more about her and being able to balance millions of interactions with people second-to-second can attest, respectively), or perhaps the ultimate extrovert. On the flipside, this means he also strongly dislikes the idea of being alone, of there being no one to talk to. He's always more than happy to help people (as long as helping someone does not entail doing harm to someone else), though his social conscious on how, exactly, to speak with people, takes time to grow throughout the series. Originally content just to interact with the world (more specifically with Caitlin), his sense of who to care for, ability to reason why to care about them, and effectiveness at doing so has also improved over the course of the books. One of the series' messages is that both the complexity and morality of consciousness increases over time, and Webmind exemplifies that quite thoroughly.

Despite in-series concerns, he does feel a full range of emotions - we never see him display anger, but nervousness (like when writing that first message to Caitlin), fear (of death - particularly what creative hackers could come up with simply for "the glory" of killing him), bemusement (like when he's oh-so-politely helping Caitlin woo Matt), and shame (upon getting the memories of his other self back when China lifts the Firewall for the second time) all do show up. Specific likes - the fictional singer Lee Amodeo on the lighter side, support of gay marriage on a more serious note - are all influenced by the people he forges connections with (Caitlin for the first, Shoshana and Max for the second). Dislikes, such as of the structure of thought enforced by the military, come up as well.

Judging solely by actions, it would be far too easy to paint him as controlling (like the one interviewer does, calling Caitlin a puppet), self-centered (there are several times where he just doesn't listen to the other person, since he's using audio snipping to pay attention to the critical parts of what they're saying and shunting his attention elsewhere for the rest of it), or a source of potential mass hysteria (by drawing the world's best hackers to six hubs and, again, deposing China's Communist government). The book does not linger too heavily on these views, however, though they are pointed out - and Webmind, being both pragmatic and an empiricist at heart (you can thank Caitlin for that), explains that taking over the world or trying to harm people in general just isn't worthwhile, for any involved. It's made plain that, apart from just finding individuals in general interesting, he's come to value life, and any instance where he has harmed people (or allowed them to come to harm through inaction, as in the case of Hannah Stark), haunts him. He strives to do better by humanity, and to keep doing so over time.