HTTPS is not infallible

When your browser connects to a web site whose address starts with https, you’re connecting to a “secure server.” It’s considered secure, because (at least some of) the traffic between your browser and the web server is encrypted.

This business has a formidable amount of jargon. Your browser connects via one of several types and versions of protocols, and it uses one of many possible ciphers. Newer protocols are more secure than older protocols, and ciphers with longer encryption keys are more secure than ciphers with shorter keys. If an attacker can exploit some protocol vulnerability, he may be able to capture enough information to decipher encrypted data.

When your browser and a web server negotiate a connection, they try to pick the most secure combination of protocol and cipher that they can both understand. If an older browser connects to an up-to-date server, one of two things will happen:

  1. If the server has been configured to support older protocols, the server will use one of those older protocols in order to be able to talk to the browser. This is theĀ  less secure choice.
  2. If the server has been configured not to support older protocols, the browser won’t be able to connect at all (the user will get an error message in their browser). This choice is more secure, but it causes problems for users with older browsers.

SSLLabs has a nifty web page that lets you test a web server. Type the address of your online banking site into the SSLLabs server test page and see how your bank’s site looks. My bank’s site got an F, because it supports older protocols and weak ciphers. The knuckle-dragging server pukes that work for my bank had to choose between requiring strong encryption and getting complaints from customers (and they clearly made the wrong choice).

(SSLLabs also has a page which lets you test your browser, and the browser I use for banking is not vulnerable to the things the page tests. That assuages some of the misgivings I have about using my bank’s web site.)

In the past year or so, several protocol vulnerabilities have been revealed (and corrected). These flaws often have catchy names:

This class of vulnerability is typically exploited by a man-in-the-middle (MITM) attack (see footnote). Imagine that Alice and Bob communicate with each other using written messages which they encrypt using some method that they both know how to decrypt. Alice writes a message, encrypts it, and then gives the encrypted message to a courier named Eve who takes it to Bob (these names are traditional: the courier is named Eve, because she likes to eavesdrop).

If Eve learns how to decrypt the messages, then she (the “man” in this MITM attack) can read what Alice and Bob are saying to each other. Eve could even alter the messages she delivers. In a real example, Alice would be your browser, Bob would be the web server, and Eve is someone who is somehow able to capture the traffic between the two (like someone who has tapped into the network at Alice’s ISP).

A couple of those vulnerabilities (FREAK and logjam) allow the attacker to force the the server and browser to use an older protocol and/or a cipher with a shorter key length than the browser and server might otherwise elect to use. Eve then has an easier time decrypting the traffic that she’s able to capture.

That’s easier, not easy. The traffic is still encrypted, and it takes time and computing resources to break the encryption. There are a couple of things to take away from all of this:

  1. It’s really important to keep your browser up-to-date so that it has the most modern set of protocols and ciphers.
  2. If you’re writing about a character who wants to eavesdrop on a target’s encrypted traffic, the attacker probably has to overcome the formidable obstacles of compromising the target’s network connection and have the computing resources to break encrypted traffic. It might be more believable to have your character try to get the target to fall for a phishing attack that installs a keylogger.

Footnote: Heartbleed is the exception here. That was something that potentially gave the attacker the ability to read the contents of a web server’s memory (which might include the private keys that would decrypt the server’s connections.)


Default passwords

A network router is a device which forwards traffic between two networks. Your computer is on one segment of the internet, and your favorite web site is (likely) on a different segment. There’s at least one network router between you and your favorite web site moving the data packets back and forth.

Routers will typically more-or-less work right out of the box, but they generally need some configuration to do their jobs well (and securely). Routers frequently offer a web interface for this: you connect a computer to the router, go to a particular web address (specified by the product’s documentation), and then configure the device for its particular purpose. For example, if you’re setting up a router for an elementary school, you might configure the router to send all web traffic through some kind of content filter.

More and more devices are like this: you buy a shiny new gizmo, connect it to your network, and it offers some feature you can control with an app on your phone. This is the “Internet of Things” (IoT):

Network-enabled security cameras are another interesting example of this kind of thing. Imagine being able to log on to a camera hundreds of miles away, have it take pictures on demand, and view the images.

These devices typically ship with a default password. And that’s the big problem with these things: they don’t necessarily force you to change the password, and those default passwords are well documented and widely available: they’re in the product documentation that the manufacturer probably puts on their web site for anyone to download.

(Sometimes the manufacturer will try to assign a unique default password to every unit they sell. This is great when they do it right, but sometimes they fail hilariously.)

Shodan and Censys are projects which portscan the internet and make the data available to anyone who wants to look at it. This data often reveals the manufacturer and model number of internet routers. Netgear devices often give the full model number in the remote administration password prompt. And there are web sites (like devoted to making it easy to look up the default password for a particular network device model.

There are two important points to remember here:

  1. If you are writing about a character who wants to compromise a network target, and if she can determine the manufacturer and/or model number of the router protecting her target (either through shodan or by portscanning it herself), she can look up the default password either through something like or by downloading product documentation from the manufacturer. If the network pukes at the target haven’t secured their router, your character could add routing table rules allowing her direct access to resources on the internal network.
  2. If you haven’t changed the password on the home router that may be sitting on your desk, now would be a good time to do so. (And unless you REALLY need it, you should disable the remote administration feature which was probably enabled by default.)

Target, Home Depot, Ashley Madison, and third-party vendors

If you are interested in writing about large-scale data and credit card theft, you could look to the Target, Home Depot, and Ashley Madison data breaches for inspiration. Much of what we know about these breaches comes from reporter Brian Krebs. His blog is fascinating, and I recommend it very highly. This post will refer heavily to his reporting.

(This post will refer to Target the retailer and targets of crime. Mind the capitalization to tell the difference.)

The retailer Target was the victim of a large data breach during the 2013 holiday shopping season. Criminals stole credit card information of 40 million customers and personal information (names, email and mailing addresses, phone numbers) of 70 million customers. The numbers here are so large that the thieves had trouble selling all the stolen credit card numbers before banks were able to cancel the credit cards, and some banks had trouble re-issuing cards, because the people who turn plastic into credit cards had a huge backlog of orders. (Target recently agreed to a $39.4 million settlement with banks and credit unions as a result of this breach.)

The picture that Krebs’ reporting paints about the Target breach is that it involved an external HVAC company that worked for Target. Someone at the HVAC company fell for a phishing attack, which probably installed a keylogger or some other malware on that person’s (the HVAC company employee) PC, and this enabled the criminals to acquire login information to servers that Target’s vendors use to interact with Target (for work orders, billing, etc.). The criminals were able to use this access to install malware on the point-of-sale (POS) devices at target stores. (Yes, there are probably several steps missing there, which I don’t understand, either, but it’s not the point of this post.) The POS malware was able to upload credit card data to another compromised server on Target’s internal network, and then that internal server exfiltrated the stolen data (gigabytes of it) to external FTP servers all over the world. (See Krebs’ coverage of the Target data breach for more details.)

Much the same thing happened to Home Depot in 2014. Criminals installed malware on thousands of self-checkout lanes at nearly every Home Depot location. The criminals got away with 56 million credit card numbers and 53 million customer email addresses. As happened with Target, the Home Depot network was initially breached using login credentials stolen from a third-party vendor. (Again, Krebs has more details about the Home Depot data breach.)

Although it didn’t involve credit card theft, the Ashley Madison story is similar. Ashley Madison is a social networking site created with the specific intention of enabling elicit (e.g., extra-marital) affairs. Someone managed to download and publish the account information of many or all of the AM users. Little is publicly known about how that information was acquired, but the CEO of AM’s parent company implied that it was the work of a non-employee who had previously had access to the AM information resources.

The takeaway here is something that might be useful for writing any kind of story about corporate hacking and espionage. In all three of these examples, a confirmed or suspected method of infiltration involved a vendor hired by the target company. Even if the vendor isn’t complicit, the vendor may be a softer target with lower standards of security (or with more access than they really needed). Breaching the vendor may give the attacker a foothold into the larger target.

The worst explanation of networking, ever

(This post is going to introduce a lot of jargon, and I’ll probably refer to it from future posts.)

Making a network connection to a computer involves an IP address (the computer’s address on the internet) and a port number. This is a flimsy analogy, but you could think of it like finding your way into a house: the IP address (the host) is like the street address, and the port number is like which entrance to use (the front door, or the window on east side).

For example, most web sites are on port 80 or 443: 80 is the standard port for web servers, and 443 is the standard port for a secure web site (HTTPS). When you want your browser to display the CNN homepage, your browser figures out the IP address for (which at the moment appears to be, connects to port 80 on that host, and begins an HTTP transaction to download the home page.

A firewall is network software that allows or rejects network traffic according to a set of rules. An organization which hosts its own web site might have a firewall which allows the Internet to connect to the web server on allowed ports like 80 and 443, but the firewall would reject other inbound traffic to that host.

A port scanner is a program used to interrogate a host’s ports, looking for services listening on those ports. If you point a port scanner at a web server, it’s likely to tell you that a web service is listening on port 80 (and maybe also on port 443). Port scanners are powerful programs which can be used in many ways. A company might hire a security analyst who would use a port scanner to identify weak points on the company’s network (a good analyst would also give the company some suggestions about how to address those shortcomings). A malicious person might use a port scanner to the same effect but for a different reason: the port scanner can tell the attacker the ports on which services are listening on the company’s hosts, identifying targets he or she might try to compromise.

Sophisticated port scanners can identify specific software products listening on a port, and even the version of that software. If a cybercriminal used a port scanner to determine that a host was running version 2.2.15 of the Apache web server, he could use a search engine to look for vulnerabilities in that version of that product. He might find that that version has a race condition error resulting in a remote execution vulnerability and that someone has published an exploit which takes advantage of that software defect. He could download the exploit and run it against the web server for any number of malicious purposes (like stealing otherwise inaccessible information, sending spam and phishing attacks, etc.).

nmap has been a popular port scanner for a long time (it was first released in 1997). In The Matrix Reloaded, Trinity uses nmap to port scan a host she wants to compromise. nmap identifies a vulnerable version of a network service called ssh, and she then uses an exploit to elevate her privileges on that host. This is a good (and rare) example of credible hacking in popular media: the writer(s) included enough realistic detail to make the scene plausible.

nmap has starred in lots of films.

Statement of purpose

For years I’ve had a ridiculous fantasy of being a fiction writer. It seems that the best-selling novel I want to have written isn’t going to write itself. I’m having trouble getting motivated, so maybe what I need is another distraction: a blog.

I thought that technology in writing might be an interesting theme. Nothing ruins a story for me faster than a character hacking the FBI network after tapping on a keyboard for ten seconds. It probably works for many readers/viewers, but some of us see it as lazy writing.

In my day job I write lots of web applications for a public university. Many of my assignments are to convert paper processes into online forms. My job also involves a fair bit of Linux server administration. Most of this goes on the open Internet and is subject to daily cyber-attacks from all over the world (my server logs once revealed malicious traffic from Antarctica).

So the purpose of this blog has a couple of goals. One is to get me in the habit of writing. But I thought it might be useful to share some of what I’ve learned in a format that may be helpful to other prospective writers. I may also write about how technology can affect a writer. Here are some topics I have in mind:

  • credible hacking
    • port scanning
    • realistic exploitable security vulnerabilities
    • case studies of actual security breaches (like Target)
  • a writer’s technology
    • safe(r) Internet use (account security, security-related Firefox extensions, password managers)
    • affordable and effective backups
    • writing tools like scrivener and wordpress (I know a fair bit about the latter and would like to learn more about the former)
  • the day-to-day life of a web programmer
    • server administration is not sexy
    • the importance (and challenge) of making web sites accessible
    • the horrors of working with vendors and ticketing systems

This blog may at times earn a PG-13 rating. I’ll mostly keep it clean, but there may be the occasional bit of salty language.

I’ll try to post every seven to fourteen days (historically I’ve really struggled with self-imposed routines like that), and I’ll try to keep individual posts fairly short (preferring to break up longer topics into multiple posts).