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Throughout the seventh book in particular, the Death Eaters spend a considerable amount of time and effort developing inside men in all kinds of areas through the Imperius Curse (various individuals in the Ministry), intimidation/fear (Peter Pettigrew in the Order of the Phoenix), and coercing people to cooperate (e.g. by kidnapping Luna Lovegood to force Xenophilius Lovegood's cooperation).

Dumbledore, of course, took time to develop inside sources

Most notably, Severus Snape

but the Order wasn't aware of them. (I suppose that's why they're called Confidential Informants).

That being the case, why didn't the Order develop more inside sources? It seems like several of the more disgruntled Death Eaters (e.g. the Malfoys) may have been willing to flip voluntarily (or they could've been coerced to with the Imperius Curse).

Why didn't they do that?

Edit: I'm not so much asking about a current Order member trying to join the Death Eaters as a mole; I'm more asking about the Order compromising someone who's already a Death Eater through some means (e.g. Finding someone who's disgruntled, coercing someone, or using the Imperius Curse).

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    I mean, you can't really be a convincing Death Eater mole without being prepared to do some pretty horrific things to prove you're evil, fooling a Legilimens, and getting the Dark Mark, so that'd be somewhat of a barrier.
    – DariM
    Mar 30, 2017 at 4:04
  • @DariM That's true - but what about compromising people who were already Death Eaters (either by finding someone who's disgruntled or using an Imperius Curse)? Mar 30, 2017 at 4:22
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    Finding someone who is disgruntled - they'll seek out the Order by themselves, like Snape, or killed, like Regulus. Imperius Curse - risky. People can throw it off, like Harry, or it can wear off,and then they'll be in even more danger, being then their attempted spy could tell the Death Eaters about the Order.
    – Mithical
    Mar 30, 2017 at 6:55
  • @Mithrandir Those are good points - that could be an answer, actually. Mar 30, 2017 at 12:26

2 Answers 2

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Voldemort was an extremely skilled legilimens. It would take someone with the same skill in Occlumency (eg. Snape) to be up to the task and not co compromise oneself. Also, being with the Death Eaters would mean commit murders and other atrocities to get close to Voldemort and his inner circle.

Also, we are talking about very small groups of people both sides, association (or even sympathies) with either The Order or Death Eaters was common knowledge. An Order member would face very strong suspicion at least, before they could access any useful information or do some other harm to the enemy.

So Snape appeared the only one capable of undermining Voldemort.

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To post @Mithrandir 's comment as an answer:

Finding someone who is disgruntled - they'll seek out the Order by themselves, like Snape, or killed, like Regulus. Imperius Curse - risky. People can throw it off, like Harry, or it can wear off, and then they'll be in even more danger, being then their attempted spy could tell the Death Eaters about the Order.

There is strong textual evidence that the Malfoys were trying to get back in Voldemort's good graces, so maybe they wouldn't have flipped on Voldemort after all.

However, Draco refuses to say that it's Harry when the Trio was captured and brought to Malfoy Manner, and Draco's mother lies to Voldemort about Harry being dead in exchange for Harry tipping her off about Draco was still being alive. Those aren't necessarily evidence that they would've flipped on Voldemort, though.

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