Beginner's guide to encrypting everything
November 12, 2016 10:36 PM   Subscribe

I've decided it's finally time to figure out all that security/ encryption/ anonymity/ privacy stuff that the EFF is always talking about. Where do I start, and how much hassle am I looking at?

I'm moderately tech-savvy, use Windows 7 (and a Mac for work, but I don't think I can encrypt that); have a work iPhone and a not-yet-activated cheap Android phone. I have several portable drives, ranging from 4gb thumb drives to a couple of 1tb drives. I also have several older laptops (Win 7, WinXP) and a couple of older desktops (Vista and something older) buried around the house.

I have a VPN service that I've poked at a little bit. I've used the TOR router thingie in the past; gave it up for speed. (I was on dialup at the time.) I have some idea how PGP and similar processes function, but have not worked with them. I am aware of Open Whisper Systems, the EFF's Security Starter Pack, and probably a few other things that aren't coming to mind at the moment. I'm fluent with portable apps and prone to throwing my favorites on new flash drives.

I have considered getting a new computer (laptop, probably) and putting Linux on it... I have some ideas of how this could be done; I attempted it once a few years ago and failed miserably.

Other details: I'm a Windows, MS Office and Acrobat power user; switching to Linux would cause problems with all of those. (Yes, I know there are substitutes. I'd still be losing years of speed and efficiency.) I'm weak on command line work, but could pick it up with practice. 2 adult kids have Win7 laptops; they and husband have Android phones. I can likely convince all of them to enact some security measures, but not to the point of either great inconvenience or requiring extensive setup.

I have no idea where to start. New hardware? Make XYZ software changes to existing computers/other hardware? Sign up for services first, or do encryption things first? Start creating new online identities first? ... Something else?

I won't say "money is no object," but several hundred dollars for a transition + $20-$50 a month is certainly on the table.
posted by ErisLordFreedom to Computers & Internet (5 answers total) 51 users marked this as a favorite
Here's a beginner's guide I just ran across today and shared on Facebook. is a good jumping-off point if you want to go all the way down the rabbit hole.
posted by jordemort at 11:36 PM on November 12, 2016 [3 favorites]

Links to two other open threads.

I have no idea where to start.

Threat model (copy-pasting from a previous answer):
What are you most afraid of and who do you want to hide information from? Your ISP knowing which sites you're visiting? Relatives/coworkers with access to your device impersonating you? A thief stealing your laptop with all your family pictures? Advertising companies tracking you?

Before you do anything else, you must know exactly what your goals are. Make a detailed list. No one here can help you with that.
Then read beginner guides like EFF's to understand which of your goals are possible and what tools you'll need. Only then will you know how much you'll have to spend (if anything).
Finally, read those tools documentation to learn how to use them and what pitfalls to avoid. Ask here or in the appropriate channels about any doubts you have.

Always keep in mind two things:
1. No matter how much you learn and how hard you try, a sufficiently motivated and resourceful adversary will always get you;
2. Almost certainly the above will not apply to you so, as long as you achieve a basic understanding and use it appropriately, you'll be better off than not doing anything and you'll contribute to normalising the practice of using privacy software, providing cover for others who need it.
posted by Bangaioh at 3:34 AM on November 13, 2016 [4 favorites]

I've started blogging about this here. I hope I can give you some useful ideas. One of the biggest things would be, in my view: get your data (the part that's not inside your own machines) off of US soil, as much as you can.

You have older machines that you don't use anymore... that's great. Put Linux Mint on one of those, and start exploring it. You won't use the terminal much, maybe not at all; Linux has evolved towards the userfriendly side of the spectrum. Switching from Win7 to Mint 18 Cinnamon is easier and more pleasant than you might expect.
posted by Too-Ticky at 3:36 AM on November 13, 2016 [4 favorites]

And here's a general tip:
One of the best things you could do would be to attend a cryptoparty: an interactive workshop about cybersecurity, often aimed at beginners. Find out here when and where they are happening. A good place to ask about this would also be your local hackerspace; hackerspaces are physical spaces (as in, buildings/rooms) where people get together to tinker and to share knowledge about many things, cybersecurity being one of them.
posted by Too-Ticky at 5:08 AM on November 13, 2016 [1 favorite]

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