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Suppose we are on a compromised computer (for example infested with trojans logging key presses or taking screenshots) and for some reason we have to generate a number that's supposed to be secret for the purpose of using in a script.

Using ruby, when I do something like Random.new.rand, the random number generator is seeded with the current time, process ID and a sequence number. Considering the characteristics of these kinds of malware, can you think of any better sources of entropy we can introduce to the seed which are harder to capture?

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    If the computer is compromised, do you have a reason to believe that the attacker can't simply read that number after it's been taken from the secure source of entropy? Or that approach/code that you implement will be faithfully executed instead of skipping your true_random and replacing it with an attacker-chosen value before it's used? – Peteris Feb 1 '18 at 0:12
  • As an extreme example: it's possible that a compromised computer is recording every possible input (including values from the network or hardware random number generators) and is running in a deterministic way such that the attacker can play back and debug any computation that was done and inspect any transient values. – Macil Feb 1 '18 at 0:32
  • @AgentME I'm not sure that would be possible for a modern IBM-type PC. There is too much not-totally-deterministic behavior (jitter in the PIC timer, etc) that would make it hard to calculate the state of the entropy pool just by recording inputs. You would have to run a flawless cycle-accurate emulator, and a cycle-accurate emulator for a modern x86 IBM-type PC is simply unheard of. – forest Feb 1 '18 at 3:14
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    if it's hacked, how do you know it's even ruby, and not something provided by the attacker? – dandavis Feb 1 '18 at 12:17
  • @forest See rr-project.org, which can deterministically record the inputs to and replay runs of many x86 programs, including the QEMU VM software, which a whole OS and any software could be run in. -- I'm actually surprised that my extreme example is as realistic as this; the point of my example wasn't that it's realistic exactly as described, but that it easily illustrates a large set of the things an intelligent attacker would be technically able to do with enough effort. The fact that it might actually be realistic now is neat though. – Macil Feb 2 '18 at 23:54
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If the machine is compromised - there is nothing that you can introduce to make it harder to capture - they own the box, the memory and the OS.

From what little I understand of Ruby as well the choice of Random is wrong for anything to be secured as it is only a pseudo-random number generator and instead you should be using SecureRandom.

With SecureRandom you won't need to try and find other sources of entropy.

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    If the machine is compromised, the ruby you think are using may in fact be a ruby created/modified/hacked by the intruder such that SecureRandom generates a string the intruder can predict. – RedGrittyBrick Feb 1 '18 at 19:55

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