These days most corporations that require end-to-end email encryption use commercial email services or appliances that allow secure email to be sent via HTTPS-enabled sites. Most commercial users of these services or devices say they are easy to implement and work with, but can sometimes be very expensive.
On the personal side there are dozens of secure email offerings. The most popular (and widely used in many businesses) is Hushmail. With Hushmail, you either use the Hushmail website to send and receive secure email or install and use a Hushmail email client program (available for desktops and some mobile devices). You can use your own, original email address, which gets proxied through Hushmail’s proxy services, or obtain a Hushmail email address, a cheaper solution.
Hushmail is one among dozens of secure email providers currently available.
Secure chat. Most OS- and device-provided chat programs do not offer strong security and privacy. For strong end-to-end security you need to install an additional chat program. Luckily, there are dozens of chat programs, both free and commercial, that claim to offer greater security. Some require installation of a client app; others offer website services. Most require all parties to communicate with the same program or use the same website (or at least the same chat protocol and protection).
Common secure chat programs include ChatCrypt, ChatSecure, and Cryptocat. Most secure chat clients have the same basic features, so pick the one that enables you to communicate with the broadest set of people you need to securely chat with.
Secure payments. Most payment systems are required to store lots of information about you and your purchases, and they are usually required to provide payment or payer details when asked by law enforcement. Even if they aren’t required to provide detailed data to the police or governments, many payment databases are compromised each year by malicious hackers.
Most users wishing for greater payment anonymity on the internet are turning to online cryptocurrencies, such as bitcoin. Users must first buy bitcoins, usually via traditional online payment methods, and must go through bitcoin exchanges to get their bitcoin value back out into traditional currencies. Each exchange into and out of bitcoin typically takes a small payment fee.
Of course, the privacy and anonymity of virtual currencies comes with real risk. They are usually not considered legal currency and may not be provided the same protections under law as “real” currencies. They may also have incredible price volatility, with the value of your holdings potentially jumping or declining by huge margins in a single day. It’s also possible that a single crypto attack could result in permanent, unrecoverable loss. Hackers have been successful in stealing millions of dollars in bitcoins, and sometimes those thefts are not reimbursed by the compromised holders.
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