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The Iron Web is an anarchist novel by Larken Rose. I read it on 2020-05-17. It is above average, and the only story I've seen that correctly identifies the *US* government as illegitimate and terrorist.
Why you should be an anarchist
The biggest issue plot-wise is that the main characters end up playing little or no role in the fall of the state. About a fourth of the way through, hints are made at a plan that would've taken the story a radically different direction (having Jessica go to Mexico and tell her survivor story), but it doesn't end up happening and felt like failed foreshadowing.
The plot is very stagnant. The siege of the anarchist camp covers pretty much the whole story, so there are very few plot developments, mostly character ones.
There is another failed foreshadowing, of the opposite type; the goodguys are saved near the end of the book by Willard Hargrove's cellar which was never even hinted at before it was used.
I think the biggest realisticity issue is survivability. A POV character survives a plane being shot down by a missile, apparently without a parachute, is not taken to a real hospital, and is only temporarily injured. *Many* times, characters survive bullets similarly (in one case, three). I'm no expert on the topic, but I'm pretty sure you don't get shot - even in the ankle - and then survive in the wilderness for multiple days with only the most primitive of medical attention.
As for the siege that takes most of the story, I think it's unrealistic that the besiegers didn't just flatten the place for real. Once they used tanks to level some buildings, I'm not sure what they were waiting for.
While it's beautiful that the book openly portrays the US government for what it is, there are several scenes that mar its didactic purity.
One is when goodguys are arguing about sending a message to federal agents who are sieging their encampment. An excerpt goes:
Jason: "If you think anyone who disagrees with you is a heartless, evil bastard, how are you different from the guys out there who think you're a bunch of terrorists?"
Tasha: "Good point, Jason. ..."
No, it's not a good point because the difference is that one side is the aggressor and the other is not. This same logic could've been used against people who resisted Nazis in WW2 to argue that if they thought all Nazis were heartless, evil bastards, they were somehow no different from the Nazis.
Tasha continues: "I think if we give up on trying to win the rational debate, we've lost already. If we can't win the hearts and minds of people, hopefully including the people who work for the government, then what's the point?"
The point (to be fair, another character argues this, but he doesn't do it very well and it's jarring that he's the only one trying in a room full of anarchists) is to stop aggression. That's still a good point if you can't win hearts and minds. That's not to say winning hearts and minds isn't important, but it's completely separate from *the point* of fighting for peace. And Tasha of all people should understand this perfectly well. There were other characters in the room who would've been better to use for this.
In another case, the book reinforces the belief in the special immorality of killing when a character tells the story of how he killed a serial rapist. It acknowledges that his actions were justified, but very weakly; the character himself says that "killing is always an evil, even when it's a necessary evil", and that it "will always kill some part of you too". This is a false and destructive message.
Another case is when they introduce the term "lasering", a gun community term for briefly pointing a gun at someone while moving it around. It's said that one of the goodguys "smacked" another the first time he did this, so hard that he almost fell over, and said "a sure consequence trains you better than a hypothetical one". That's called aggression. It's absolutely unacceptable, and is especially out of place in a book critiquing the aggression of the state.
When the same aggressive person is teaching a woman to shoot, she asks him about this and he says he "only hits male students". He self-identifies this as sexist in a sort of joking way.
The surprise kiss trope is romanticized.
Of course there are a lot of debates with statist characters about anarchism. In general, they're pretty well-done: the statist characters' arguments are as good as statist arguments can be, and their reactions and their slow conversion are realistic. Many of them are surprisingly non-preachy: they don't have an obvious portrayed victor and don't feel like "just lay out all the statist arguments in a line so I can shoot them all down and be done with it" (which is how it's come out every time I try to do something like this in fiction).
None of the characters deploy argumentation ethics (even though I think Larken himself believes in that), which is wonderful as that would've prevented me from recommending it. Some of the conversations take a welcome dive into an angle underrated by libertarians: conscience. In one case, a character is led to almost the same thoughts that led me to Chaos Anarchism, but luckily has better guidance than I did.
There are a couple of messaging blunders, mostly when the goodguys use "communism", "socialism", and "collectivism" as if they're all already negative ideographs to the reader, when the latter two are not likely to be such outside of libertarian communities. "Collectivism" is especially shaky. And to someone who isn't used to seeing all of those words as negative ideographs, there might not be an obvious connection between them and state violence. The ideology labels sound intellectually sophisticated, which clashes with the emotional leveraging of police brutality.
The worst sentence in the book is in some of the preachiest dialogue where it's suggested that "the supposed solutions to racism and poverty offered by the collectivists had done even more damage to minority communities than even overt slavery had". That's absurd and repulsive.
The book also (leaning on the fourth wall a bit) recommends the reader to read Ayn Rand, which I think is a serious mistake (she was not only a NAP purist but a minarchist and likely a major source of the libertarian movement's myopia on corporations).
All of the characters act authentic, many have very deep backgrounds, and Team Good is very diverse: it features a pacifist, a Christian priest, a former marine, and a *constitutionalist*. It's not like all the goodguys are ideologically perfect. An ATF agent is a main character who turns good.
(DISCLAIMER: the following paragraph was written before 2020.) In general, Team Good seems like a very realistic sample of the people who would actually be fighting this battle. Most of them exude a similar culture to American constitutionalists, which makes sense since most libertarian anarchists are former minarchists and still occasionally appeal to the constitution, and many minarchists talk about how the second amendment exists *so that* the people can overthrow a corrupt government. Most real minarchists wouldn't dream of putting their money where their mouth is, but if the revolution did happen now, I'd expect it to contain a lot of them.