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I have a Truecrypted, airgapped (no internet connectivity at all) laptop that I use as a completely secure computer for sensitive files.

I want to add images from my iPhone (I know), camera or other device. What is the safest way to do this? I know safety will have to be compromised in some way, but I need to best. Here's my thoughts:

  • USB: On a normal computer, transfer the files from camera to usb. Then from usb to airgapped laptop. Problem: malware could transfer from normal computer to airgapped laptop via USB.
  • Upload from iPhone to internet, connect directly from airgapped laptop temporarily before returning to internetless state. Problem: internet access is dangerous.
  • Upload from camera to Tails booted from any PC. Transfer to formatted USB, then transfer to airgapped laptop. Problem: very slow, inconvenient and Tails may have driver problems with certain devices.

Is there an obvious solution I am missing?

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I would trust a USB or SD card over transferring it via an Internet connection.

Once you put the gapless computer on the Internet, you have no idea what's going to come down the pipe. Applications might start auto-updating, in which case you are downloading and installing EXEs from untrusted sources over an untrusted network, which is exactly what you are trying to prevent by keeping the machine off the network.

To your third point, TAILS should not be confused with a secure OS. It's not. It's a TOR proxied OS. The purpose of TOR isn't security, it's a limited form of privacy. Instead of trusting your local ISP, you are pushing your trust to TOR exits, but you know nothing about who is actually running those TOR exits. It could be a black hat. It could be GCHQ.

When an attacker controls your network, as in the TAILS architecture, there are all sorts of new types of attacks they can potentially use against you, such as DNS spoofing, malicious code injection, etc. So, I'd stay away from TOR or TAILS when you are looking for a secure environment. It's not their purpose and in fact creates more threats.

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How do you know your laptop is truly air-gapped? Did you physically remove the WiFi and Bluetooth chips in it? Or it is inside a Faraday cage? I would put it in Faraday cage to be properly secure from TAO's bag of tricks. Otherwise an NSA van might drive past and remotely activate some chip inside your laptop and exfiltrate data off it.

If you had another machine you do not particularly care about, you could connect your iPhone to that, copy the photos to it, then write them to a CD/DVD/Blu-ray. Turn off auto-play on the air-gapped machine. Take the disc to your air gapped machine. Then scan it for malware. Then copy the images across. That would avoid the recent USB security issue.

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