Re: overwhelming, start with the basics; a foundation.  Once you understand the UNDERLYING TECH, the rest, is much, much easier to understand.  Book I wrote (2001?) ... to get newbies to understand PGP (public key cryptography; what runs pretty much everything under the hood.  Download (free):  https://mega.nz/file/jsplULpR#4K6CmI1YqCSRZhiAj83hRHqi9DBpTkdIt0hWzilV3v8 Read chapters 3 (PGP) and if you want to go full cypherpunk, chapter 4 also (remailers). Chapters 1 and 2 were written back when no one understood the very basics of online security (thus are unlikely to be of personal relevance to you, you'll already get that bit).  You can cover to cover the entire book in around 1 hour 20 minutes (tops).