Given the size of the thread, I've only found like 8 or 9 mistakes which is pretty impressive. As an oxford comma user, I'd add more commas to sentences, paragraphs, and statements. :)
see wut i did ther?
Anyways, onto the content. Just a quick comment on each of the topics:
1. Secure Operating Systems
As far as security goes, Tails and Whonix are certainly among the top in terms of anonymity, but I'd be careful calling them "secure." I'm aware that this is not meant to be an operating system security thread, but people can be identified by insane things like screen resolution or cursor movements. Everyone using Tor needs to ensure that they disable all client-side code execution (javascript, flash, etc...) as that is the #1 way of identifying Tor users. It seems to me that tunneling an entire TCP/IP stack via a single SOCKS proxy would lead to issues. Hats off to the Tails community for developing such a great product.
2. Virtual Private Networks
As a very pleased Proxy.sh user, I can personally attest to their security, anonymity, and simplicity. To point out the obvious, that picture with the 1's and 0's followed by a picture with ampersands and pound signs is obviously ridiculous. We know what they're trying to get across, but data shows up as 1's and 0's anyways. The only difference would be that the original picture would resolve to human-readable ASCII (assuming that was the original goal) and the other would be nonsense to a human. At any rate, I'm just happy you cleared up the misconceptions about DNS leaking. It's not some occultish, magical hack. It's just using local DNS servers to resolve things like PurchaseCreditCardsOnlineForCheap.com coming from your IP. The best thing to do is to use remote DNS lookups (which Proxy.sh supports) as opposed to using, say, Google's DNS servers. Your ISP will still get metadata, and I wouldn't be surprised if they captured all DNS requests. So thank you for giving a great explanation of DNS leaking.
3. TOR Related
It looks to me like you've covered all the major topics (and more!). Quite simply, Tor is a multi-tiered encrypted communication network via numerous community-run overlays and a potentially malicious exit node 🤝 Exit nodes really are a pain in the ass. NSA-run exit nodes that inject client-side scripts into unencrypted communication is a very real and unfortunately common activity. I know I mentioned client-side scripts in the Tails/Whonix part of my post, but it is very important and I think you clearly demonstrated the necessity for it. To give an example, the largest Tor-based child porn hosting service, Freedom Hosting, was taken down by a couple of lines of JavaScript.
4. Encryption
You're a bigger man than I if you want to tackle such an incredibly diverse, robust, and rigorous topic as encryption. Though I'm far from even pretending to understand the deeper mechanics of encryption, the mathematical Theory behind it is incredible. I would want to point out that even today's encryption is still subject to attack. Hopefully no one here actually needs to be told that with the POODLE's and the LOGJAM's and the HeartBleed's of the past few months. Obviously you want to stay encrypted, but since the majority of the population does not care enough to run encrypted email services, making the job of an attacker significantly easier, it gets annoying having to send passwords and the likes using
https://oneshar.es and
https://privnote.com and such. I would add in the software that KMS was talking about in the TeamSpeak that encrypts RAM. I am not familiar with cold-boot attacks (essentially blasting ice cold air into the RAM and preserving the state so that you can move it into anther computer and find the disk encryption keys) and their popularity in forensic environments, but it may be relevant to anonymity. I will say that Tails has protection against this attack. Kudos.
5. File/Download Security
I don't have much to say here. Several of the Next-Gen firewalls that I work with have the capability to perform malware analysis on files being downloaded; it's interesting to say the least. Metadata is always a problem, but there are many ways to change it (as you mentioned). Antiviruses, Rootkit protections, and host-based IDS's are imperative in a secure environment. If you have a ring-0 or kernel-land Rootkit, everything else is subject to the attacker's whim.
6. Social Related
i'm not much of a social media person, but don't post or message anything relevant to your passwords or security questions. It seems like it should be common sense, yet it remains elusive to the morons that, unfortunately, are allowed use the internet.
7. General Computer Security
Like encryption, this is too big a concept to discuss in such a limited space. I'd recommend putting in things like GRSec for MAC (mandatory access control) and RBAC (Role-based access control) as well as buffer overflow protection, and a myriad of other things. I also like OSSEC as an HIDS. It's cross-platform, centralized for simplicity and security, and is incredibly easy to deploy.
It's not much, but it's a quick
Goodies' Goodies segment. Big thanks to Zer0 for creating such a unique and much-needed thread. I hope it gets the recognition it deserves.