Cellphone Economics Revisited: Two Years In

I have now saved myself a full cellphone contract. Two years ago, I devised a plan to save myself a ton of money by overhauling my cellphone service plan. Last year, I reflected on how much I had accomplished and discussed some potential tweaks to my system. To recap, two years ago, I was paying $576 per year for a no-frills, mediocre phone plan with no included text messages. Last year at this time, I had reduced that amount to less than $190. This year, I have continued to cut my usage, and I am happy to announce that I only paid about $130 for my cell service. This includes 1000 prepaid T-Mobile minutes (purchased last April for $100+tax) and $26.55 for a 1-year Skype subscription. Over the last two years, I have saved $832 compared to keeping my traditional cellphone plan. I’d just like to take an opportunity to pat myself on the back. It wasn’t always easy, and I did occasionally use Sadie’s phone on the weekends, but otherwise this plan was a fantastic idea. A lot has changed over the past year and more change is coming in the future, so all of this could potentially affect what will happen to my plan in the upcoming year.

I’ll be the first to admit that as I looked back through my records I was surprised to find that I had not bought any minutes for my prepaid T-Mobile plan since last April. I just ran low enough at the end of March 2011 to finally buy some more. As I mentioned above, a few things have changed for me this year. First, Sadie and I got an apartment together in Chicago. I no longer make hour-long nightly phone calls to her. Although I previously used Skype to make these calls, there were always occasions where we would have longer conversations on the phone when using a computer wasn’t practical, such as while I was driving.


CC-BY-SA by echiner

A few things changed technologically as well. Not only is it now possible to use Google Voice with a free VOIP client, but Google has integrated free voice VOIP calls into GMail and the Google Voice Web app. Since I commented last year on the quality of Skype calls, I’ll comment on Google Voice VOIP calls today. They are not as clean as Skype, but they are improving. The call quality sometimes degrades, randomly cuts out, or even drops. This is especially true if I’m doing anything else using the network, including browsing the web while talking on the phone. I rarely experienced these problems with Skype VOIP calls. Overall, the call quality seems to have improved over the past few months, but it is still much more temperamental than with Skype calls. However, what it loses in quality, it makes up for in convenience. I almost always have a GMail tab open, which means that incoming calls now ring my computer and outgoing calls are just a click away. Plus, Google Contacts makes it easy to store and dial multiple numbers for all of my email contacts. This makes the Google Voice interface quite a bit more usable than Skype’s client. Google Voice also offers free text messaging, and messages are delivered to your GMail account just like a traditional email. Since my Skype subscription is lapsing in a few weeks, I find myself asking, “should I renew my Skype subscription or just stick with Google Voice?” I am leaning towards sticking with Google Voice because I can get incoming VOIP calls through GMail, Google Contacts’ phone number organization, and it’s free. Over the past 6 months I can probably count on my fingers how many calls I’ve made using Skype, so it seems silly to continue paying for it. On the other hand, it’s quite inexpensive, and it’s a good backup to have if my Google Voice call quality is poor.


I will also be starting my residency training at the Medical College of Wisconsin in Milwaukee in a few weeks. Sadie and I will be moving in June. This throws a number of new variables into my (currently very efficient and cheap) plan. I don’t think my current minute usage will change much. I make calls to my family and Sadie using a mixture of Google Voice when it’s convenient and my cell when it’s not. I am unsure how much residency will eat into my minutes though. While I’m at the hospital for longer hours without frequent access to GMail for checking text messages or listening to voice mails, this will undoubtedly result in more calls on my cell and thus more minutes used. That’s not a bad thing; it’s just a fact.

There’s another interesting twist in all of this. According to our Program Director, anesthesiology residents at MCW get a free iPod Touch. The department started posting podcasts through iTunes U to facilitate quick reviews of common anesthesia topics between surgical cases, and the iPod Touch is their nice gift to allow everyone to access the podcasts. No one mentioned if we will be receiving these this summer or if we will have to wait to get them until next summer when we start our official anesthesiology training. Since the new iPod Touch can be paired with a Bluetooth headset and its Google Voice and Skype apps work over WiFi, this could work as a convenient make-shift phone at the hospital and at home.


CC-BY-ND by samantha celera

And then there’s the elephant in the room. Starting in July, I’m no longer going to be a poor medical student. Technically, I’ll be a poor Resident Physician, but at least I’ll have this thing called income. I keep wondering whether it’s time I break down and get an Android smartphone. (At the time of writing, it would most likely be a Nexus S.) Part of me says I should, but I still have some reservations. My biggest concerns are monthly price and value. Currently, I’m spending about $10 per month on cellphone service. Can I really increase that 7-fold? More importantly, will I derive enough value from a smart phone to justify the increased expense? At this point, it’s not really about the money. It’s about feeling that I’m not getting ripped off by my wireless provider. I’m not going to use many minutes, and I’m not going to use much web data since I’ll almost always have Wifi around. Ever since T-Mobile dropped their Even More Plus plan, I feel like wireless companies no longer care about what their customers want. I want to buy an unlocked, full-price phone and get a cheaper monthly bill with no contract. I want plans that have less than than 450 minutes and are priced accordingly. I really want a data-only plan with the option of adding on talk time. Instead, wireless providers are generally trying to keep you locked into an over-priced smartphone contract with a required, bundled data plan (usually $25-30/month). This results in people paying for a lot of stuff that they don’t use.

Then, I see people like Dave Pell and David Siegel who point out that too much Internet connectivity can disconnect you from real life. I have enough trouble with controlling my Internet time on a laptop, so what’s going to happen when my Internet is with me 24/7? So here I sit with my old cellphone. I’ve had my Sony Ericsson W810i for 4.5 years. The battery still lasts 4 days on a charge. After paying my dues to Cingular and AT&T for 2 years, my subsidized phone is unlocked and transferable to any GSM carrier by switching out a $5 SIM card. I can place calls, text, listen to music, and connect to my laptop via Bluetooth.

I guess I have some decisions to make. After reading I Will Teach You To Be Rich, I’ve been doing a lot of thinking about conscious spending. In the book and on his website, the author discourages people from passing judgement on others for their spending habits. When budgeting, after “paying yourself” by contributing to savings, he encourages consciously spending money on things that you value and mercilessly cutting spending on things you don’t. The goal is attainable because it doesn’t require people to consistently tell themselves “no” and it encourages them to understand what makes them happy and to do it as much as their budget allows. Now, I just have to decide whether a smart phone brings enough value for me to consciously spend my soon-to-be, hard-earned money on it.

Facebook and the Email Apocalypse

So in case you haven’t heard the rumors, supposedly Facebook will release “Project Titan” on Monday. As rumor has it, they will be introducing a web-based email system that’s built into Facebook. It will replace traditional “messaging” on Facebook with a full-fledged email system. It will likely include your own @facebook.com email address. Some are calling this a Gmail killer. I tend to agree with the other side, who find that assessment laughable. Of course, by “laughable” I don’t mean that it will be unsuccessful. On the contrary, I’m sure it will be quite popular as far as numbers go. It’s just that I remember email before Gmail and how much they changed the game. I am highly skeptical that Facebook would even be able match Gmail in terms of utility and ease-of-use, and I find it laughable that they would be able to innovate enough to draw me away from Gmail’s clutches.

No doubt there is a market for integrating email into Facebook. As a user of both Gmail and Facebook, I got to thinking about what might happen in the coming months given what I know about the past.

First, Facebook email will almost certainly create a rift among emailers. To me, the division will be between those who use email as a tool and those who use it as a toy. I could easily see some of my friends and family, young and old, who spend the majority of their time behind Facebook’s walled garden anyway, integrate Facebook’s inbox into their life and slowly forget about their prior email addresses. “Email that’s separate from my Facebook account? That’s so 2010.”

In fact, that’s kind of Facebook’s plan, right? The whole goal is to take over the Internet by making their own Internet inside of Facebook. Do you want to play a game? Why go to another site when you can play lots of them on Facebook? Do you want to share photos with your friends? Why go to another site when you can do it on Facebook? Their whole goal is that you never have to leave, and adding a way to communicate with the “outsiders” will take away another major reason to leave their site.

But as I alluded to earlier, those of us who actually use email to communicate with 10, 20, 50, or even 500 people a day, we want a system that is made specifically to make that process more pleasurable. That’s what Gmail is, and I find it nearly impossible that Facebook will be able to rival Gmail’s feature-set. Remember, that’s not even their goal. Their goal is to make it functional enough to keep you from leaving their site. Ever.

It’s one thing when Facebook adds a feature I won’t use, but I’m not sure their integrated email system won’t actually be detrimental to their platform as a whole. I mean, do you remember email in 2001? (or even 2007?) In addition to loads of emails offering me all sorts of adult content and attachments that would infect my computer with viruses, there were links to sites that would steal my banking credentials and hijack my Paypal account. Oh, and that’s not to mention the deluge of weekly email forwards pleading with any and every excuse to have me forward this chain letter to my entire address book. Gmail has largely hidden spam from me.

Does Facebook have a plan in place for when the spamming masses come down on their email system with phishing links and social engineered trojan horses? Because I hear about enough people now whose Facebook account and email accounts get hacked. Wait until their email is their Facebook. It sounds like a recipe for disaster. I shudder thinking about this, but imagine the eventual hacks that start messaging all 600 of your “friends” and writing spam ads on their walls. Won’t that be fun for your girlfriend from 6th grade who you haven’t talked to since junior high and your boss at work, both of whom are your “friends” on Facebook.

My solace lies in my apocalyptic hope that this venture shows Facebook for the house of cards that it is. Facebook has been largely preserved because of their ability to keep spam out, aside from user-selected spam. By opening up their floodgates to the world of spammers, the site will become much less navigable by average folks, which could cause a sizable exodus. I wonder how people will react when they realize that so much of their lives that they have poured into Facebook over the past months and years is lost in that walled garden? And where will these users go when they are left alone in this largely unexplored Internet.

So what do you think? What have I missed? What good or bad will come from Facebook’s integration of an email system?

Cellphone Economics Revisited: One Year In

Last year I devised a plan to save myself a ton of money by revising my cellphone service. I was paying $576 per year (including taxes) for a mediocre cell plan from AT&T. I’m happy to report that my plan has been a fantastic success. Using this plan, I managed to pay $188.56 (including taxes) for my phone service for the entire year. That includes $162.01 for 1500 prepaid cellphone minutes and $26.55 for a 1-year Skype subscription. The Skype subscription is really the key here. I made a 30 to 60-minute phone call on average of 4 nights/week, every week for a year, for $26 total. That’s pretty amazing. Otherwise, I would have been using about 720 minutes/month to talk to Sadie on my cell every night, in which case talking to her with a regular phone plan including “free” nights and weekends would have been cheaper.

With my heavy reliance on Skype, you’re probably wondering what the service is like. To be honest, it’s better than I expected. I very rarely had a dropped call, and for the most part the sound quality was quite clear. Sadie even told me that she was impressed with the call quality, saying it sounded just as good as if I were calling from a cell.


CC-NC-ND: Jason Nicholls

Were there any downsides to using Skype? Only a few minor ones, some of which I had predicted. Unless you sign up for a SkypeIn online number ($30/year), when you call someone who has Caller ID, your number shows up as something crazy (like 0001123456789), and it’s always different. This scared a lot people who weren’t used to it, since they had no idea who was calling. Sometimes my mom still screens my calls with the answering machine. I could have also gotten around this by buying some Skype Credit, which can be used to disguise Skype calls as ones coming from my cell number. I need the credit in order to send and receive a text message from Skype to my cell to verify the number. I would have done this long ago, but unfortunately the lowest amount of Credit you can buy is $10. I would have had $9.80 worth of Credit still sitting in my account. I decided to save my money and live with the inconvenience for the time being. I also had an issue with poor call quality using my Skype-to-Go calling card, but it significantly improved at some point last Fall.

As serendipity would have it, Google Voice also launched last year. I linked my new Google Voice number to my cell number so that I can give out my Google Voice number and it will ring my cell. Then, if I ever decide to buy a SkypeIn online number, I can tell Google Voice to ring my cell and my computer when someone is calling.

So what is my plan for the future? At least for the next year, I plan to keep doing what I’m doing. I may splurge and buy a SkypeIn number and hook it up to Google Voice. It would not only stop the Caller ID problem I mentioned, but it would also allow me to receive phone calls on my computer, which would be a big help. I would say that at least half of my cellphone minutes are used because someone is calling my phone, and I can’t answer it on Skype. The only thing keeping me from doing that right away is the rumor that Google Voice is soon going to become a desktop VOIP provider and thus a direct Skype competitor. If they can offer competitive rates to Skype, I may have little reason not to use them. Of course, Skype is likely announcing an open-source client, which would be fantastic. Then it will be a battle to see who provides the best quality service, the best price, and the best open-source/Linux compatible platform. It’s shaping up to be quite a year!

On a related note, LifeHacker picked up this topic today. As I posted in their comments: Every time that I have the urge to get a smart phone, I cringe at how much more it’ll cost me every year for features that I don’t even need, and I quickly remember why I don’t already have one 🙂

Show your support

Advertising is a huge business on the Internet. Actually, advertising is huge just about everywhere.

Some readers get annoyed by bloggers who use referral links in posts to promote products that will ultimately make them money. They feel like the Internet should be free of ads, and in some ways they’re justified. Occasionally, bloggers use these posts purely to generate money for their site (i.e. the post is simply a commercial), but others are just interested in telling their readers about a new product that they’ve discovered. And there’s a difference between promoting products that you use and love and just being a shill. In the same way, from a potential buyer’s perspective there’s a difference between watching a commercial or listening to a sales pitch telling you that Chevy makes the best cars and having your friend who’s a mechanic tell you how reliable Chevy’s are.

A lot of people (myself included) get annoyed by the amount of advertising on the Internet. It’s easy to become dismissive of the pop-up flashing pictures and AdWords, but I think there’s something to be said for people and sites that provide a service or take the time to tell you about a product that they use and enjoy. For example, last year I had never heard of the group Vampire Weekend, but I discovered their newest album on The Hype Machine Zeitgeist 2008 and really liked it. When I decided to buy the album, I made sure to click the referral link from The Hype Machine website to Amazon MP3 so that they’d get credit for my purchase because, in all honesty, they deserved it. We (as Internet consumers) need to embrace this and actually promote effective advertising. If a person, blog, or website grabs your interest enough for you to purchase something and they offer a referral link, give them credit and help them make a little bit of cash. It encourages them to keep doing what they’re doing and it usually doesn’t take any charity on your part.

If enough people take the time to encourage those who are advertising effectively (and unobtrusively), it will send a message to the industry that quality is at least as important as quantity in advertising.

I also feel compelled to promote less tangible goods. I use a lot of free software every day. It’s easy to forget that most Free and Open Source Software (FOSS) developers are working in their free time, which could easily be spent with their friends and families. Many such developers accept Paypal donations or offer an Amazon wishlist for people to donate from. A number of bigger software projects also sell merchandise that helps make them money. If you (consciously or unconsciously) have trouble convincing yourself to donate money, this is a great alternative that allows you to get something in return. I encourage people to buy these things for me as gifts, and I buy some myself. So far I’ve got 2 Firefox shirts and 2 xkcd shirts. I’ve got a list of quite a few other projects that I plan to support by purchasing merchandise in the future.

Advertising is a huge business on the Internet. Make sure to remember that you, the consumer, have the power to reinforce effective advertising and to support people who make your life better without providing a tangible product. If you provide useful information or reviews on your website, it might be a good idea for you to provide referral links that can actually get you something in return for your work. And before you buy your next purchase online, stop and consider who or what influenced your purchase. Is there any way for you to give them credit for it? If we could all capitalize on this word-of-mouth advertising, it would (hopefully) decrease the amount of in-your-face advertising that plagues us all.

Side note: Don’t get the wrong idea. This post is in no way implying anything about my wanting to make money from this blog or for projects that I support. It’s just a statement on advertising in general.

Medicine in an electronic age

The following is the fifth (and probably final) post in a series entitled, “Securing your Email.” I’ve spent the majority of the series talking about logistical things like why secure email is important and how to get started with public-key cryptography. If you look back at my first post, you’ll see that the reason I went out and learned all of this (and wrote about it ad nauseum) is because I feel like it’s an incredibly interesting and important topic where medicine meets technology.

Communication throughout the world is becoming more and more electronic, and things are changing rapidly. In the field of medicine five years ago, most institutions (including very large hospitals) were still using paper records. In fact, even today a number of institutions still do. Doctors communicated by telephones and pagers, and records from other facilities were carried in by hand or faxed. With the technological advances in the last 10 years, today a physician could easily be consulted halfway around the world with a simple email, and a copy of an X-ray or CT-scan could be sent electronically. These changes in the way health care is administered presents a new set of problems to the industry.

This electronic age spawned a strong concern about health care privacy in the United States, which was addressed by HIPAA. The health care industry spends an incredible amount of time and resources dedicated to preserving people’s privacy. They spend millions and millions of dollars on “enterprise level solutions” to make sure that they can work online safely. These are not always dollars well-spent, but that’s the topic for another day. Unfortunately these solutions end up restricting health care professionals in such a way as to reduce the utility of the system. As an example, I’m going to talk about email (as you might have guessed).

As I pointed out in my first post, I’ve been thinking about this for a while. How in the world can health care institutions, who are so concerned about privacy and protection of their patient’s data, not be doing more to provide secure email solutions? I think I’m in an appropriate position to answer that question. I’m part of a committee that has been charged with selecting a new email provider for the hospital. We’re currently looking into a number of different vendors, and a question that consistently comes up is about “email security.” We’ve got a number of people on our committee including people from IS, the legal department, and human resources staff as well as physicians, nurses and students. Their “email security” questions have the best intentions. They want to make sure that the solution we choose is going to keep our patients’ data safe.

At the same time, however, I feel like there is a knowledge gap as to what they know about email security. I feel like most (if not all) of the people involved just want someone to say “your email is super-duper secure with our system.” One vendor took it a step further and started talking specifics of cool stuff that their system can do to prevent, for example, someone from emailing Protected Healthcare Information, or PHI, to someone outside of Rush. The problem I (and some members of the legal department) have is that sometimes this information needs to be sent out, for example to a lawyer’s office. From a patient’s perspective, if I request that my physician contact me via email with my lab results as opposed to over the phone, should that be discouraged? But it is, and that’s because some of the people in the IS departments across the land realize how insecure email is. So we need to make it more secure, and in order to do that, we have to understand where its security flaws lie.

The problem is that most institutions don’t look at the problem like that. They don’t get an unbiased assessment of email security. Instead they get a vendor to sell them an “email security solution” in which the vendor defines what secure email is and how their solution fits the bill. I’m not saying that all companies are giving a false sense of security, but it’s definitely a concern. It’s exactly why you have to understand the problem before you go looking for an answer. Things would be significantly different if a group of people like the “free software community” assessed a health care institution’s email security needs. In fact, the purpose of my post is to propose the following: the health care community should embrace the free software community’s model of email security.

Health care institutions have all the right resources already in place. They simply need to implement it. It would be fairly easy the create a public key server for your health care institution. When Housestaff and Physicians begin their tenure, they could easily be required to create a key pair during new employee orientation. Key pairs could be distributed on cheap flash drives for safe keeping and stored on a private server for easy access while on campus. Alternatively, keys could be distributed on smart cards. Since an institution has verified who an employee is, their internal web-of-trust will form easily. As long as someone’s public key has been signed by the company’s IS department, it can be trusted. These key servers could be made to exchange keys with those of other institutions or even external key servers, such as one set up by the NIH or the Department of Health and Human Services. Physicians also often travel to conferences, and “key signing parties” or booths could be set up to create a more full-fledged web of trust.

Having public keys freely available would make it easy for physicians to communicate more securely with one another. They’d be able to trust an email from a colleague. Plus, they’d be able to encrypt emails and attachments containing PHI. Physicians would also be able to communicate with their patients via email more freely. Patients could be given instructions how to acquire the physician’s public key and how to use it. It would be even better to set up a way to simplify the process by just emailing the patient a link so that an encrypted email could be viewed directly on the institution’s website. They wouldn’t need to worry about having the proper GPG client software installed, since they’d just have to click a link and the web page would decrypt the email for them.

Unfortunately, there are many in the health care IS industry that would rather none of this communication go on via email. They are probably smart to have a firm stance that no PHI should be communicated via email at this point since their email system is probably very insecure. The problem with their plan is that both now and in the future PHI is being sent via email and it’s probably not going to stop unless some serious consequences are put into place at individual institutions.

I have to wonder though. If the email system was actually set up securely and properly, why couldn’t PHI be sent via email? Why shouldn’t I be able to request my test results in electronic format from my doctor? These aren’t questions that are going to be addressed by any single institution, unfortunately, and this presents a very big problem in the near future. A number of other industries are currently caught in a downward spiral because they chose not to adapt to the Internet era. Does a similar fate await a health care industry that wants to deny physicians and consumers access to the PHI electronically under the guise of HIPAA and “we know what’s best” for protecting patients rights? Doing so is just going to drive the process more underground, giving them less control over the situation in the future. They’d be better off embracing the idea now and preparing for the future of medicine in an electronic age.

Safety Dance

The following is the fourth post in a series entitled, “Securing your Email.” So far in this series, I’ve done a lot of talking about the theory of secure email and why you might want to make your email more secure. If you’re not familiar with these concepts, I strongly urge you to go back and read the rest of this series. In this post, I’m going to highlight how you can get started using public-key encryption today, using only free software.

Disclaimer: It’s important that you read this entire post before attempting anything. It is perfectly acceptable to create a “test” key using a fake name and email address. Just make sure you label it as “test” and that you delete it (or revoke it) when you’re done. Also, creating a key is (somewhat) serious business. Only create one if you plan on using it and keeping track of it.

Before we begin, we need to get a few terms out of the way. First, I’ve oversimplified one point up until now. I let the term “encryption key” have multiple meanings. An “encryption key” is actually an “encryption key pair.” Each pair consists of a “public key” and a “private key.” As you can probably guess, a “public key” is meant to be shared with anyone and everyone. For example, here’s mine. It is meant to be your public electronic identity. If anyone wants to check whether I truly wrote an email that I’ve digitally signed, they can use my public key to verify the authenticity of the message. A “private key” is never meant to leave your possession. Never, ever give someone access to your private key. It is the lifeline of your electronic identity. It’s used to digitally sign outgoing messages and to decrypt any private mail sent to you. Your private key is still passphrase-protected, so as long as you’ve chosen a strong passphrase, your key is relatively safe even in the wrong hands. This is why it’s important to use an extremely strong passphrase when creating your key: uppercase and lowercase letters, numbers, and symbols that is at least 8 characters long. It is almost certain that your passphrase will be the weakest link in the security of your key. Check out this article by Microsoft to learn more about creating a truly secure passphrase.

Let’s take a minute to understand how public and private keys work together. Basically, you are the only one who uses your private key, and everyone else uses your public key. For example if I want to digitally sign an email, my private key takes a snapshot of the outgoing email and attaches a small digital signature to the message (attachment: signature.asc). The signature is tied to the exact text of my email. If the contents of the message is altered en-route, it will not validate when it reaches the recipient. When you receive my email, FireGPG or Enigmail will see the signature.asc attachment and analyze it using my public key, which will be retrieved from the Internet if it’s not on your computer already. If my message has not been altered, the signature shows up as “valid.” No matter what, the message of the email will be visible, and if the recipient does not use any GPG-capable software, the email will look normal (except for a simple signature.asc file attached to it).

Encryption and decryption work differently. If I encrypt a message to you, I want you to be the only one able to read it. So, I encrypt the email using your public key. The text of the email is encoded, and the only way to read the original message is for you to decode it using your private key. Nobody else can read the message (unless they’ve somehow stolen your private key and cracked the passphrase). Not to get too technical, but you can actually use digital signatures and encryption at the same time. For example, I want to send you a message that is meant only for you (encryption), and I want you to verify that I actually sent it (digital signature).

Ok, enough talk. To get started creating your key pair, you’re going to need to install a piece of software called GNU Privacy Guard (GPG or GnuPG for short) on your computer. Somewhat confusingly, GPG is a free software implementation of the OpenPGP standard. PGP stands for “Pretty Good Privacy,” an ironic acronym considering that it’s extraordinarily secure. Windows users can download and install Gpg4Win, which should contain everything you need to get started, including the WinPT keyring manager. I’ll discuss more about what a “keyring manager” is in a moment. It looks like a new version of Gpg4Win is due out in a few weeks if you’d rather wait, but you shouldn’t need to. Mac OS X users can install MacGPG, which should likewise contain everything you need to get started. Linux users almost definitely have GPG installed on their system by default along with a keyring manager (like Seahorse for Gnome or KGpg for KDE).

GPG by itself uses a command-line interface. Since most users want a more robust interface, they install additional applications that harness the power of GPG and make it available via a more user-friendly point-and-click interface. The “keyring managers” that I mentioned earlier provide this interface. A keying manager is an application that keeps track of other people’s public keys so that you can verify their digital signatures and encrypt emails to them. They keep track of the trust level of these keys, and they can be used to sign someone’s public key if you want to confirm their identity. A keyring manager can also be used to generate a new key pair for yourself and keep key pairs in sync with the many online public keyservers in the world. As I mentioned in a previous post, if you want to use GPG to sign and encrypt emails, you need to use a browser extension or a desktop email client. Gpg4Win comes bundled with an extension for Microsoft Outlook. Enigmail is a fantastic extension for Mozilla Thunderbird that can serve as a keyring manager and desktop email interface for GPG. FireGPG is a great Firefox extension that can serve as a keyring manager and a GMail interface for GPG. As you can see, software developers, many of whom need to send secure emails every day, have developed a great set of tools that make getting started with secure email fairly easy.

Unfortunatley, I can’t ouline all the possible ways to use this software. I’m going to go through a few examples here and provide some links to relevant documentation. In general, to create a new key for yourself you need to enter your “key manager,” for example by going to “OpenPGP -> Key Management” in Thunderbird (with Enigmail installed) or “Tools -> FireGPG -> Key Manager” in Firefox (with FireGPG installed). Then you want to generate a new key pair by going to “Generate -> New Key Pair” in Enigmail or click “New Key” in FireGPG. If you’re using Gpg4Win without Enigmail or FireGPG, you can follow this guide (although it looks a little dated, and you may want to use the WinPT key manager over GPA). Make sure you enter your full name and the email address you plan on mailing from. The “comment” field can be left blank, unless you’re creating a “test” key. It’s up to you whether you want to give your key an expiration date. (Most people don’t.) If you’re feeling adventurous, check out the advanced options. While most key managers should use these advanced options by default, you want your key to have the following options: “Key size/length: 2048” and “Key Type: DSA & Elgamal.” It will probably take a minute or two to generate your key. Make sure to move your mouse around and do something like browse the Internet, which helps create a strong key. Once your key pair has been created, you’ll be able to add additional email addresses to it if you plan on using more than one.

If you are asked whether you’d like to create a back-up your of key pair and/or create a revocation certificate, do it. If you are not given the option to back up your key pair and you cannot figure out how with the software you’re using (either “back up” or “export” your public and private keys), you may need to use an alternative key manager or the gpg command line tool. For example, FireGPG does not allow you to export a private key (only a public key, which is not an adequate back up). If you are not given the option to create a revocation key/certificate and you cannot figure out how with the software you’re using, you should create one using an alternative key manager or the gpg command line tool. You should back up all three of these files (your public key, your private key, and your revocation certificate) on a USB flash drive, external hard drive, or blank CD and store it in a safe place. This is especially true if you created a key pair without an expiration date. This will be your fall-back so that your key is never completely unusable.

I should take a minute to explain the revocation key (or revocation certificate). It can be used to “revoke” your key pair if it is ever lost or stolen. It will be used to notify public key servers that your key is no longer valid, and it will tell your friends and colleagues to no longer use this key. This is obviously something you want to keep private as well, since someone could easily revoke your key if they got ahold of it.

Now that you’ve hopefully got a functional key pair created, you’ll want to take some steps to enter into a web-of-trust. First, you have to publish your key to one (or many) of the free pgp/gpg key servers. There are likely a few built in to your key manager, like hkp://pgp.mit.edu and hkp://pool.sks-keyservers.net. You can also manually upload your public key to the PGP Global Directory (make sure it’s not your private key!). Now your friends and colleagues can use these key servers to keep track of your public key.

To get your own web-of-trust started among your friends and colleagues, you will need to exchange two numbers with them (usually in person). Your “Key ID” should be fairly apparent in your key manager. Mine is D4188BF6. Your “Key Fingerprint” should also be available through your key manager, but you may need to do a little bit of digging into the key via “Properties.” Mine is C14A 6784 162F 9C42 E404 D37F E5B6 FD50 D418 8BF6. You might notice that the last 8 digits of my key fingerprint match my key ID. These numbers will allow you to positively identify my correct key on a public key server. Thus, you can be sure that if I gave you that key fingerprint, I am in possession of the corresponding private key. If you can positively identify me, you should sign my public key and synchronize that signed key to the key server. Once I do the same for you and more of our friends and colleagues do the same, a web-of-trust will begin to form. Using this, I can reasonably trust people that I’ve never met if their keys are signed by my trusted friends and colleagues.

I realize there was a lot of terminology thrown around in this post that you probably weren’t familiar with. I apologize for that. I also apologize for not giving step-by-step instructions for individual key managers and software. I thought it would be better if I gave more general instructions that should be applicable to any key manager. There should be guides, documentation and forums available to give specifics for most of the popular key managers. If you’re having trouble with that (or anything in this entire series), leave me a note and I’ll see if I can clarify things for you or point you toward an answer.

I’m basically done with “new educational material” for this series. In my final post, I’m going to outline some ways that the medical community could use the tools described here to change the means of communication between health care providers. Since that was my original intent of this series, I hope you’ll tune in for the final installment. It may have a lot of “what ifs,” but it should be interesting to think about.

Who do you trust?

The following is the third post in a series entitled, “Securing your Email.” If you’re just tuning in and you’re not very familiar with words like “digital signature” and “public-key cryptography,” you may want to take a few minutes to read the first two posts in this series.

After reading my earlier posts, hopefully you’ve gotten a better understanding of what digital signatures and encrypted emails are and why they can be necessary. Before getting into the technical details of how to obtain or create an encryption key, you should gain a better understanding of how keys are authenticated. After all, this entire process is about learning to trust a system more than a plain old email. So why should you trust an email with a digital signature more than a normal email? How do you know whether that digital signature is even valid? Your recipients need a way to verify that your digital signature actually belongs to you. There are two competing theories (or “schemes”) about how this should be done, each with advantages and disadvantages. Both involve “verifying” that the identity of someone’s key matches their true identity in real life. A key is considered “verified” when a person or company signs the key. By signing a key, the signer is asserting two things: the person is who they say they are and their identity matches their key.

In the public key infrastructure (PKI) scheme, a certificate authority is responsible for this verification. You’ve probably heard of Verisign, the most popular certificate authority. Certificate authorities are companies who take responsibility for verifying that your key matches your identity (as determined by a driver’s license or passport) in exchange for a fee. For example, an individual “Digital ID” from Verisign costs $20/year. Thus, for a fairly nominal fee you get a verified encryption key that can be used to digitally sign or even encrypt emails. In order to do this, you’ll need to use a desktop email client, such as Microsoft Outlook Express or Mozilla Thunderbird, or you’ll need to use a browser-based plug-in for web email, such as the GMail S/MIME extension for Firefox. It’s important to realize that your recipients also need to use one of these applications to be able to check your digital signature or decrypt your email messages.

While the PKI scheme costs an annual fee, nearly all of the work and upkeep is done by the certificate authority. The user simply has to purchase the key and start using it. Cost aside, however, many people in the computer industry do not trust keys that are signed by certificate authorities simply because the companies can be easily subverted. In other words, they do not trust that the certificate authorities are doing their jobs thoroughly. People claim that for your $20, you can get a certificate identifying you as basically whomever you want. If true, this destroys the integrity of the entire system. Once they have your $20, does the company have a significant interest in whether you actually are who you say you are? You also have to wonder how much you can trust a lesser known certificate authority. For example, if you got a message from Joe, whose key was verified by Jimbo’s Certificates, would you be more likely to trust Joe’s signature? Less likely? Also, what happens if a certificate authority goes bankrupt?

As an alternative to PKI, the web-of-trust (WOT) scheme is used. Instead of a central company (or set of companies) in charge of certifying people’s identities, groups of users validate each other’s identity. You first need to create an encryption key on your computer, which I will cover in my next post. Your key will have a “digital ID number.” You then need to meet in person and exchange “digital ID numbers” with your friends and colleagues. Once you’re back at a computer, if you’re satisfied with someone’s identity you can use this number to locate their key on the web and sign it. You’re essentially saying, “I met this person, and I can confirm their identity and that this is their true key.”

Using this scheme reduces cost (it’s free), and thus eliminates the bias of companies that are more concerned with profit than actual validity. Plus, multiple validations for a given key should greatly increase your ability to trust it. If 15 of your close friends have verified Joe’s key, would you be more likely to trust Joe’s signature or less likely? A disadvantage of the WOT scheme is that without a backing company, it is usually a lot more work for the individuals. You can’t just pay someone $20/year to take care of it for you. It also usually involves meeting face-to-face with people in order to verify their identity or have them verify yours, which can be difficult for some people depending on where they live. Fortunately, with the advent of free software tools like key servers, it is really easy to assess the trust level of a person’s key.

As with PKI, you need software tools to be able to digitally sign or encrypt an email. You’ll also need this software to be able to verify someone’s signature and decrypt an email. Some examples of these tools are the Enigmail plug-in for Mozilla Thunderbird or the FireGPG Firefox extension for GMail. I will go through how to use these two applications in more detail in my next post.

Now that you’ve got a good background on how key validation works, you’re ready to get started with your own key. If you’d like to purchase a key from a certificate authority, go for it. Unfortunately, I can’t describe how to use it in detail since I’ve never purchased one, but some of the information I’ll provide may still be helpful. In my next post in this series, I’ll show you how to use free software to create your own encryption key right on your computer for free. I’ll also discuss how to use it and how to get started in the web-of-trust.

Fixing the Holes

The following is the second post in a series entitled, “Securing your Email.” Throughout the post, I am going to be referencing an analogy about mailing a letter that I described in the first post of the series. If you’re not familiar with it, you may want to take a minute to read it. I’ll wait…

There are a number of ways you can make email a more secure form of communication. One of the easiest ways to start patching holes in your current system is to look for major lapses in security and take care of those first. In my analogy, multiple security threats could be effectively eliminated by handing your postcard directly to the mail carrier and having your boss’ mail carrier hand it directly to him or her. That way, the postcard is never left sitting in an insecure location. There’s no chance for a random person walking down the street to read, copy, or change your message. If you really trust your postal workers and your message doesn’t contain too much sensitive information, this may be all the protection you need.

The equivalent in the email world is making sure you do all of your communication to and from your email provider over a secure connection. This is actually really easy to do, as long as your email provider supports it. Since GMail is fairly ubiquitous these days, I’ll use them as an example.

You want to make sure you’re viewing, sending, and receiving email over a secure connection. If you’re using a web browser to access GMail, you just need to make sure you log in using https://gmail.com (note the https). GMail also intelligently offers an option to “Always connect using https,” which makes sure you never forget and leave a postcard sitting out by the curb. I highly recommend enabling that option if you haven’t already. If you’re using a desktop mail client like Outlook or Thunderbird to access your email, make sure you specify a TLS or SSL connection when you’re setting up your account. By making sure the connection to and from your email service is secure, you’ve eliminated a major lapse in email security. Since many email services offer (or even require) it, it’s a good idea to get into the habit of verifying that you’re communicating over a secure connection whenever you check your email. It’s also imperative that you’re using a secure connection if you’re emailing on public networks, especially insecure wireless networks.

But what if your email service doesn’t offer secure connections? Or what if that’s not enough? Personally, I don’t think it is! If you look back to my analogy, you’ll see that there are still a number of prominent security threats. For example, what if some nefarious character at the post office tampers with your message?

The best way to deal with the remaining threats is using public-key cryptography. This is a fairly complicated topic, and I’ll only be scratching the surface of it in my posts. For now, let’s say that all you need is a file on your computer called an encryption key. In future posts, I’ll briefly cover how to obtain and use an encryption key and some of the basic theory behind public-key cryptography. For now, let’s understand some of problems that public-key cryptography aims to solve.

Flickr: Zappowbang's "Seal"

Flickr: Zappowbang's Seal (CC-BY)

In my analogy, I pointed out that upon receiving your message, your boss has no way to verify whether you were the original author. In the real world, a person uses their written signature to symbolize a document’s authenticity. Unfortunately, forged signatures are sometimes difficult to spot, except by experts. To provide an extra layer of verification, important documents that have been authenticated usually bear a seal. In the old days, many important people sealed their letters using some wax that they would impress with a unique design. This ensured the recipient that a document had not been tampered with en-route. Today, an official document whose signature was verified by a notary public also bears a seal. A digital signature is similar to a seal. It asserts that all (or part) of an electronic document was verified by the signer and that it has not been tampered with en-route. Since the documents are electronic, this makes a digital signature much more portable than a paper document bearing a seal. Unlike a wax-sealed message, digital signatures do not prevent anyone who comes across the message from reading or copying it. It is simply a indicator of the author’s authenticity.

Flickr: timg_vancouver's Engima Machine (CC-BY-SA)

Flickr: timg_vancouver's Engima Machine (CC-BY-SA)

If you need to send a message that contains extremely private information, which no one but the intended recipient must see, the message needs to be encrypted. As you can probably guess, this is means that even if someone were to examine the message text, they would not be able to read it. For example, the Enigma machine was used by the Germans in World War II to encrypt messages between their armies. An encrypted message contains a long string of seemingly random letters and numbers that have been disguised using a code. Messages are encoded so that only a person who has the proper key can unlock the code and reveal the original message. This is starting to sound a bit like a Dan Brown novel, isn’t it? Aside from that, encryption is kind of boring. It does its job really well, and as long as you pick an adequate passphrase for your encryption key, your information is fairly secure. Just make sure the Allies don’t capture your Enigma machine, or you might be sunk. 🙂

My purpose here is not to convince everyone to start using public-key cryptography to digitally sign or encrypt all of their emails. My purpose is to help you understand how insecure your email is and why this extra security is used and ultimately necessary in a lot of situations. Many of us have come to rely heavily on email as form of communication. If you are one of those people, it may be time to reconsider how much trust you place in that system. The methods that I described in this post should help restore most of the trust you may have taken for granted in the past. Still, if I can get a handful of you to start digitally signing your emails when I’m through, I will consider that a victory.

Now that I spent almost this entire post talking about strange things like digital signatures and encryption keys, you might be fairly confused. Before things get any more technical, I wanted to help you understand why we use these things and how they work on a basic level. In my next installment in this series, I’ll discuss some of the theory behind public-key cryptography and how it’s used to create an extra layer of security on top of email by establishing your true electronic identity. In the future, I’ll also cover how to obtain or create an encryption key and how to use it. Then you’ll truly be on the road to secure messaging!

Please, Mr. Postman

One of my friends has the following “signature” attached to all his outgoing emails:

The materials in this message are private and may contain Protected Healthcare Information. If you are not the intended recipient, be advised that any unauthorized use, disclosure, copying or the taking of any action in reliance on the contents of this information is strictly prohibited. If you have received this email in error, please immediately notify the sender via telephone or return mail.

I’ve seen messages like this many, many times, and I feel like they really highlight a major problem with email. This message is like someone putting a sign outside of a window that says “Warning: You are not allowed to look in this window, and if you do, forget what you see immediately.” Does that message do any good at all? It almost makes you want to look in the window more, doesn’t it?

The following is the first post in a series entitled, “Securing your Email.” I’ll start the series by highlighting the dangers of insecure email and why this topic is important. Once I’ve got you convinced that every email you’ve ever read is a fraud, I’ll use the rest of the series to outline many different options you have to address the problems.

In case you are unaware, email is an inherently insecure form of communication. If you don’t know a lot about how web servers and the Internet work, that might not be terribly intuitive, so let’s start off with a pretty good analogy. Let’s pretend there’s no such thing as email. You work from home, and you need to send your boss a fairly important message with some sensitive information in it. It’s brief, so you just grab a pencil and jot your thoughts down on the back of a postcard and stick it out in your mailbox by the curb for the postal carrier to pick up. Pretty soon afterwards the message gets picked up, and it makes its way through various post offices and into your boss’s mailbox a while later.

Ignoring how slow things went, that still probably sounds like a pretty dumb way to send an important message. Unfortunately, it’s a pretty good description of how email works. To get a better picture of why it’s dumb, let’s examine some of the security flaws present in a system like the one described above. First, you left the message in your mailbox unattended. Anyone walking down the street could just open up the box and read what you wrote. Considering the message contains sensitive information, you probably don’t want just anyone to read it. More importantly, if the person had a pencil they could easily erase what you wrote and replace it with something else.

You also place an inherent trust in the postal system. If the message you’re sending truly contains sensitive information, you need to have it available in a form that only the intended recipient can read. Then, even if someone steals your letter, at least you won’t have to worry about private information getting out.

Finally, once your boss receives the message, there is no way for him or her to verify that you actually wrote it. Did the person who opened your mailbox change what you wrote? Did someone from a competing company send your boss false information under your name? The information is highly suspect unless your boss can verify that you were the original author and that the message hasn’t been altered since you sent it.

If you’ve made it this far, you may be asking yourself whether any of this is even relevant to you. Maybe you don’t make it a habit of emailing people sensitive information, but I would bet that you’re mistaken. A lot of seemingly harmless information in the wrong hands could be used to do a lot of damage. Plus,what if a criminal tried to impersonate you for their own gain? Don’t your friends and colleagues deserve to know that you actually wrote the words they’re reading? The same applies to emails you receive from your friends and colleagues. Maybe you don’t think that anyone would ever waste their time reading, copying or altering your private emails. There are a lot of good reasons why criminals would want to do this, however. The most obvious would be to make money at your expense. Plus, some of these security flaws could be used to get you into a lot of trouble at work. Is that something you want to risk?

The rest of the posts in this series will outline both simple and more complicated steps you can take to secure your email. Since my original reason for these posts was to address email security for health care providers, I’ll include a post that demonstrates how the health care community could begin implementing more secure email today. Hopefully this analogy has taught you something about the emails you read every day. Check out the rest of the entries in the days to come, and leave comments if you have questions or think I’m wrong about something!

Windows 7: Netbook killer

The following is a prediction of things to come in the next year.

I get the feeling that Microsoft is trying to kill the netbook market with Windows 7. In case you haven’t heard, Microsoft announced a new edition of Windows 7: Starter Edition. The Starter Edition is only capable of running 3 applications at once. Their purpose for this “Starter Edition” is two-fold. First, it is meant to be a sufficiently crippled version of Windows 7 so that they can sell it dirt cheap for use in netbooks. Many people will not buy it because it can only run 3 programs at a time. (Update: MS changed their minds on this after significant blacklash from the community, but Starter continues to have other strict limitations) They’ll pay a significant premium to buy a netbook containing a “normal” version of Windows 7 (Basic or Home) because it will be Microsoft’s flagship operating system. That’s different from today’s market. Microsoft can afford to give away Windows XP for dirt cheap on current iterations of netbooks because it’s already really old, and they’re busy trying to sell Vista. Buying a netbook with Windows 7 Basic or Home will increase the total cost so much that the devices will no longer be “worth it” to people unless they really want that small form-factor ultra-ultra-portable.

Second, most of the people silly enough to purchase the Starter Edition will find it so incredibly annoying to use that they will either have to pay to upgrade to a non-crippled version of Windows (again significantly increasing overall cost of the device) or they will discount their netbook as “a toy” of little value. This attempt by Microsoft to upsell the netbook market is probably going to kill it. Any way you slice it, Microsoft-based consumer interest in the market will wane.

Then, of course, we have Linux-based netbooks. By October, Ubuntu 9.10 will be available. It will likely boot on your netbook in 15 seconds or less if it has an SSD. It will come fully featured with an office suite, IM client, email client, web browser, media player, image editor, and much, much more. Oh, and you’ll be able to run every single application at once if you want to. Graphics will be performing fantastically, and the user interface will be strikingly refreshing. And of course you’ll get all of this for the low, low price of $0. Let’s just hope that Canonical can get it installed on a number of prominent netbooks whose manufacturers won’t hide it behind a curtain so that consumers will realize that they’re no longer subject to Microsoft’s crippleware. They can have an extraordinarily functional, free system on any machine they want. Ubuntu needs to capitalize on Microsoft’s idiotic move here, and I think they will.