First hand online anonymity and security resources

I'm tired to searching and having to decipher information from posters on forums about current best practices for anonymity and internet security. I mean, I've managed to setup Tails and TOR and PGP, and I have a base understanding of how to keep safe-- but other than the explanations someone else online gives me (who I put alot of trust in) or gives someone else in an archived post, and verified by me as echoed by others, I don't know why what I'm doing is supposed to keep me safe.

I just know TOR is supposed to keep me anonymous because people say it does... I just know Tails is supposed to leave no trace because people say it does. Where can I learn the skills and material to better understand why and how these programs work to keep us anonymous as possible? I want to know why using a VPN with TOR could potentially help or hurt me. Not just some forum post, but are there books or certifications one can take to understand the stuff behind this. Or a reliable website from some kind of authority? So potentially one could be confident when communicating, setting up as a vendor, or even designing a market?

I'm just tired of my only way of learning shit is searching the reddit forums. There's got to be a better more reliable way that offers a deeper understanding?? study programming books??


Comments


[1 Points] dlayover123:

You're making much more out of this then is needed. You want to know the intricises of the program you are using to know definitively you're safe or are you just being paranoid? It seems like you have good stuff so far. Reddit is a great place for information because people tell you first hand about it. Otherwise, I'm sure there are specific subs you can find in technology where people can point you in the right direction.


[1 Points] 180K:

/r/privacy and www.privacytools.io


[1 Points] sapiophile:

There's some good starting places. I'll just list some:

If you're interested in a market, you should probably read up on Next-Generation Hidden Services, including the background stuff there like the original Proposal 224

The bitcoin wiki at https://en.bitcoin.it has some interesting discussion around difficulties of private cryptocurrency workings.

There's also some pretty solid discussion in the I2P community in general, on that network...

Oh and https://gwern.net of course


[1 Points] None:

why would you run software that you dont know what it does


[1 Points] Bbmcisrightyoufools:

Learn about encryption and traffic analysis. Cryptography engineering is a good book