Hey friends! I just wanted to say that your posts on spies have been so useful to me. Anyway, I have a character who is an ex-soldier (infantry). For various plot reasons, he needs to infiltrate a very secretive group and gain info on them. He has a mentor, who is an intel agent. Question is: what would a crash course on infiltration look like? They don’t have much time, and my solider is a very straightforward person and has some problems with deception. What does he need to know?

Well, one thing he really should not know, under any
circumstances, is that his handler is setting him up as a sacrificial lamb for
the other guys to capture and interrogate. A “spy,” who is bad at deception,
and very straightforward? He has “doomed spy,” written all over him.

The Doomed Spy is a concept from Sun Tzu’s The Art of War. This
is a spy you send in, explicitly, to be captured. They don’t know it, but their
real job is to feed misinformation to the enemy, either through shoddy
tradecraft or under direct interrogation. This could range from something as
simple as a false flag operation, where the spy is told and believes they’re
working for one nation or faction, when in fact, that entity has no knowledge
of their actions, and their handler’s loyalties actually belong elsewhere. Or,
it could be as complex as an entire operation, designed to provide the targets
with false intelligence.

So, your ex-soldier, who’s bad at lying, and thinks he’s
working for one group is, in fact, working for a completely different group that
wants to provoke action against the people he’s (probably) loyal to. This may
go a step further, where his handler recruits him, specifically because of his
prior ties to the faction the handler claims to represent.

Something else that’s kind of important to understand about
intelligence work, or at least direct human intelligence work. As a spy, your
job isn’t to sneak into an office, or even talk your way in. Sometimes you need
to be there personally, but most of the time, you can get someone else to do it
for you. Why sneak into an office building, when you can pay a member of the
cleaning staff to pass paperwork to the trash, where you can get someone to
pick it up later?

At that point, there isn’t a lot of reason to train assets
(the people a spy uses as intermediaries to get their information). In theory,
they already know how to act in their native environment.

Getting someone into some kind of secret society is going to
be a lot trickier, but at that point,
your spy’s best cover may be going in as themselves. Okay, up front, this one’s
a kind of weird situation, so let’s parse apart how this works.

Normally, a spy’s best option is to get other people to work
for them. It creates a layer of insulation, so if something goes wrong, they
can get out, and take any intelligence they’ve obtained, before the authorities
manage to close in on them. This doesn’t always work, but, the separation
between an actual spy and their assets is vital to effective tradecraft. It
also means that the spy’s identity isn’t immediately known. There’s a huge jump
between walking into a place, and having your face on security cameras, and
getting some poor schmuck no one knows to do it for you. This also leads to a paradoxical
situation with intelligence work. Spies tend to deal with their most
immediately critical cases early in their careers, when no one knows who they
are, and then spend the rest of their career working on much less important
cases, when getting exposed would be less harmful.

What we have here sounds like a slightly different situation
that doesn’t really pop up in the real world, where a spy’s anonymity wouldn’t

If we’re talking about some supervillain’s secret society,
where they already have intelligence gathering on par with some nations, and
have moles in your spy’s intelligence agency, then, as I said a minute ago, the
answer may be to go in, “as themselves.”

With one exception, you wouldn’t likely see this in the real
world, but a veteran spy, looking to infiltrate some kind of Illuminati/Majestic
12 style, “secret rulers of the world,” type conspiracy, may be better off poking
them with a stick and asking for a job. They’d already know who the spy is,
there’s no real point in pretending to be someone else. Their own skill set
wouldn’t raise any questions when that’s who
they’re supposed to be anyway
. Once they’re in, they’d probably act as a
sleeper (an agent who does not engage in any intelligence activities) to build
up their cover, increase their access, and only act when they have the opportunity
to fully achieve their goals, (which could take years).

Just to be clear, you could shove an entire series in here,
about a spy who infiltrated some conspiracy, and is building their cover and
working their way up through the ranks while wrestling with their ethics and
what they’re having to do.

In that context, it’s possible they may pick an ex-soldier
off the street to send in, in order to get the organization’s people knocking
on their door.

In general, you’re not going to see this with national
intelligence services, because no one trusts defectors. But, if you’re talking
about an extra-national service, they don’t really have the option of producing
their own talent (at least, not at first). They’d also be more likely to poach
members of their host nations’ intelligence communities.

The one real world example where you might see a spy walking
in the front door without a cover would be in dealing with businesses. Companies
who are concerned about corporate espionage have a real incentive to hire former
intelligence officers as security consultants and advisors. At the same time, this
isn’t an extremely likely outcome for a couple reasons. First, private sector
jobs like this are a very lucrative gig for ex-civil servants, meaning going
after one would be biting the hand that (would have) fed them. Second, they’d
still be in competition with other ex-intelligence officers for the position,
people with the same kinds of training they received, which would make getting
in tricky. Finally, when it comes to the business world, you rarely need a spy;
it’s overkill. Most of the things a business gets into would be better suited for
investigation by normal law enforcement channels.

Come up with a situation where a spy would need to tear into
a company’s actions, and they’d benefit more from directing police action
against it, rather than going in directly.

In all of this, I don’t think I’ve answered the direct
question. The kind of videogame, sneaking in through the vents, infiltration
approach doesn’t (usually) work. Infiltration, in the real world, is more about
walking in and looking like you belong there, not hiding behind crates and
climbing the drainpipes. (Somewhat obviously, this isn’t going to work out for
your straightforward ex-soldier who has hang-ups about lying to people.) The
biggest lessons are in social engineering. Learning how people function
(psychologically), and exploiting inherent vulnerabilities in “normal” social

Social Engineering often gets broken down into individual
tricks, that play with expectations, for example: using a business card as
false identification when making an introduction. This would never get you
through a security checkpoint, but it might get you in the building to talk
with someone, and give you access to information they normally wouldn’t.

As a gestalt, social engineering is fairly complex, but the
basics are looking for ways to get people to give you information they really
shouldn’t, by making them think you’re someone who is supposed to have access.

But, that’s what a spy’s job is, getting people to tell you
things they shouldn’t, usually by misdirection and deception.

– Starke

Two films that come to mind in this specific genre which may be worth watching are The Recruit, and Spy Game.

The Recruit (2003) focuses on a programmer (Colin Farrell) who is tapped by the CIA to become an agent, and the film spends a lot of time working through the training of prospective CIA Officers.

Spy Game (2001) focuses on a retiring CIA Officer (Robert Redford) discussing the training and career of his


(Brad Pitt). To a degree, this is probably the most on point to what you’re after, so if you’ve never seen it, it should be part of your lit review.

As always, Burn Notice’s, “when you’re a spy” routines may also be useful. The show spends a lot of time on social engineering (though it rarely uses the term). The discussions on how people normally behave, and how to work around, or exploit, their expectations are what you’re looking for.

You may also want to pick up and watch Ronin (1998). This is more about veteran spies interacting, but it has a very slick approach to tradecraft that may be useful.

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