Now, there are many problems in the world of digital security - from governments around the world undermining privacy technology or firewalling their citizens off from information to valiant but underfunded security tools having the time to focus only on keeping the tool safe, but not making it easy to use. Some of these problems are rather significant, some are more approachable, but there remains a hidden problem, so pervasive and pernicious that it undermis all of our good work in bringing usable, human-centered privacy and security tools to wider audiences.
The problem, in a word, is piracy.
Indeed, there is even a rumored "How to pirate safely" guide -- because if you can't even trust your outdated, un-updated operating system, what does it matter what you security build on top?
Why do people pirate?
The easy answer is of course economical - licensed software is not cheap; and when a license for Microsoft Office is two or three months of salary for a person, the choice to focus on people rather than tools is, frankly, reasonable. But there are other reasons - computers, especially desktop systems, are often sold with pre-pirated software installed, or your friendly computer guru "upgraded" you in the modern day version of a permissive cable TV installer. Your computer may have crashed hard, been stolen, or was confiscated; and your licensed software and that ever-valuable product key that proves you were legit is nowhere to be found (do you know where yours is right now?).
It may even not be an option to acquire legal software, if you are unable to use a credit card or acquire software from foreign countries due to restrictions or sanctions.
I've yet to encounter an activist who pirated because they were a cheapskate.
What are alternatives?
It's not for a lack of alternatives. I use one of the many well-cared-for, user-friendly variants on GNU/Linux, an operating system that is both free to install, re-install, use, copy, and so forth, but also free to play around with and edit or change if you're so inclined. The biggest problems (in my mind) are actually OEM and manufacturer support, and the Microsoft Office suite.
Queue the hatemail here :)
Let me first tack office software, as the free software world has powerful office suites - OpenOffice and LibreOffice. If you are making documents, spreadsheets, and so on, these are all you need. However, if you're collaborating with someone using Microsoft Office, eventually something will break, especially once you bring in track changes and merges and comments and such. Google Documents provides an option, but tethers you to yet another infrastructure, and still may not actually meet all of your needs.
The other challenge is hardware. This is partially because I'm picky, but making sure the components of a modern laptop will all work smoothly with Linux is not always easy - wifi cards are a huge hassle, and very hard to spot variations sold to the consumer as the same can mean the difference between everything magically working and a huge headache. Modern Linux is actually quite usable, and many design elements appearing in OSX (and even, slowly, Windows) have actually been around in Linux desktops for years. But weird hiccups in hardware support undermine all of this when the easiest solution for why your wifi randomly stops begins with "OK, first open up a command line..."
OSX of course is another alternative, and is attractive - built-in hard drive encryption at no extra cost or weird privacy-undermining key escrow -- seriously, Microsoft, get with the program, easy to use, better baseline security than Windows, more stable than Linux, and almost guaranteed to be supported (by websites, software, etc - not something you can always count on in Linux).
However, Apple devices are expensive (more accurately: unlike the PC world, there's not a low-cost option); often harder to find, and more difficult to repair. Apple continues to lock down their ecosystem, and you're still caught wrestling with MS Office or compatibility issues.
What are solutions?
I believe in two long-term wins. One is a revolution in licensing that creates a much more flexible structure for using, and re-using proprietary operating systems. The other is hardware support for open source operating systems. Paradigm-shifting privacy approaches like the Qubes operating system will be able to flourish if users can run virtual Windows or OSX machines.
More immediately, I am excited by Dell's most recent forays into "developer edition" laptops with pre-installed Ubuntu, and would love to see more manufacturers (especially those with decent hardware support track records, Lenovo...) do the same. It at least provides a known-working starting point.
I am excited to see Microsoft expand their work with TechSoup and "go global" with steep discounts to their software for qualifying non-profits, but my experience underlines that this is not enough - non-affiliated individuals, or communities working as organizations but unable to legally form an organization are at huge risk, and laws restricting organizations are spreading among oppressive regimes. In the wake of a 2010 crackdown leveraging pirated Windows to destroy an NGO in Russia, MS created a "unilateral" license program, which solved the immediate problem, but (if you can find this program! Hint - dig through the FAQ), you get a PDF download of a letter stating that you can use MS software - i.e. whatever sketchy, pirated version you're working with, you can keep!
Of course, getting people to explore options for most "word processing" outside of MS Office (hey, plain text is pretty cool!) would help as well.