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Technically the title should be Things to do With Encryption…, but then I wouldn’t have a semi-obscure movie reference. Cory Doctorow of BoingBoing linked to a column of his over at The Guardian entitled If I’m dead how will my loved ones break my password?. As a new father myself, I recently went through the estate planning process with my lawyer, and this is one issue I’ve long thought needed more attention. A few years ago I even considered building a startup around it. Much of my important data is encrypted – especially logins to bank accounts and such. Also, a fair bit of my other data is either encrypted, or protected in ways many of you fair readers could circumvent, but my family members can’t. I also have a ton of “personal institutional knowledge” in my head – everything from how to keep this blog running, to locations of family photos, to all the old email correspondence I kept when my wife and I started dating. If I get hit by a truck (or, more likely, kill myself in some bizarrely stupid way right after saying, “okay, check this out”), all of that would either be lost to the ether, or complex to recover. Heck, I have content that might be important to my family in applications in virtual machines on encrypted drives. Part of my estate planning process is ensuring that not only do my family and business partners have access to this information if I’m not around, but that they’ll know where the important bits are in the first place. Unlike Cory I’m not concerned with using split keys in different countries to prevent exposure to the government, but I also don’t think I’m as organized as he is in terms of where I keep everything. Thus, as part of my estate planning, I’m looking at the best way to make this information available on the off chance my sense of self-preservation fails to mature. Here’s the plan right now: Compile my passphrases, locations of important information, and other documentation into a single repository. I’m considering using 1Password since it already has the logins to nearly everything, I use it daily, and it can export to an encrypted PDF or a few other formats. 1Password supports secure notes for random instructions and other documentation. On a regular basis, I will export the information to an encrypted file which I’ll provide to my lawyer, and store in a secure online repository. I have a lot of options for this, but for the rest of you it might be better to set up a Hotmail/Yahoo/Whatever email account you don’t ever use for anything else, and send it there. You can then give your lawyer or executor access to that account (remember, the contents up there are still encrypted). This makes it easy to keep the information up to date, and it’s protected from your lawyer’s office burning down with your encrypted hard drive. It may be worth it to use two different services, just in case. Remember that if your lawyer doesn’t have direct access, it may be difficult for him/her to legally obtain access after death. I’ll give my lawyer the locations of the information and the passphrase for my 1Password export in a sealed envelope. Since he’s my brother in law, and might be with me when I accidentally blow up that propane tank, I’ll make sure his partner also has a copy in a separate physical location. That should cover it – my information is still protected (assuming I trust my lawyer), and it includes logins, locations of important electronic documents, and so on. I’m in the middle of setting this up, and haven’t even talked to my lawyer about the details yet, but it’s as important as any other aspects of my trust. A separate issue, and the other half of my vaporware startup, is what happens to all my correspondence/photos/movies after I die? Historically, the archives of individuals, handed down through generations, are an important part of the human record. This isn’t just an ego thing – letters and photos of regular folks are as important to historians over the ages. Right now, as a society, this isn’t an issue we’ve really addressed. Share:

Martin is off in Japan this week, so I’m joined by our good friend Amrit Williams from BigFix and the Techbuddha blog. Amrit and I start off by talking about the rolling blackouts in California and disaster preparedness, before jumping into the week’s security news. Network Security Podcast, Episode 156 Time:  41:28 Show Notes: The New York Times and Wikipedia censor reports of a captured reporter to protect him. Dave Shackleford on 10 things your auditor doesn’t want you to know. Trojan steals FTP credentials Juniper pulls ATM hacking talk from Black Hat Most systems have unpatched software. Is anyone surprised? Tonight’s Music:  Since I haven’t figured out how to get the podcasting rights to Jimmy Buffett’s entire collection, there’s no music for tonight’s close. Share:

This is Part 5 of our Database Encryption Series. Part 1, Part 2, Part 3, Part 4, and the supporting posts on Database vs. Application Encryption, & Database Encryption: Fact or Fiction are online. I think key management scares people. Application developers, IT managers, and database administrators all know effective key management support for encryption is critical, but it remains scary for most practitioners. Despite the incredible mathematical complexity behind the ciphers and the finesse required to implement those ciphers in a secure fashion, they don’t have to understand the gears and cogs inside the machine. Encryption is provided as libraries or fully functional services, so you send out clear text, and you get back encrypted data – easy. Key management worries people because if you don’t get the key management piece right, the whole system fails, and you are the responsible party. To illustrate what I mean, I want to share a couple stories about developers and IT practitioners who manage these systems. Building database applications from scratch, developers have access to good crypto libraries, but generally little understanding of key management practices and few key management resources. The application developers I know took great pride in securing database fields through encryption, but when I asked them how they stored the key, the answer was usually “in the properties file”. That meant the key was stored on the disk, unencrypted, and in a directory readable by anyone who could access the application. When I pressed the point, I was assured that the key ‘needed’ to be there, otherwise the application would not be able to get the key and thus fail to restart. I have even had developers tell me this is a “chicken vs. egg” conundrum, that if you encrypt the key you cannot access it, therefore a key needed to be kept in clear text somewhere. I kid you not, with my last employer (who, by the way, developed security products), this was the reason the ‘senior’ programmer implemented key management this way, and why he didn’t see a problem with it. The argument always ends the same: a key as a tangible object is fine, but obfuscated and hidden is not. The unspoken reason is something every programmer knows: code has bugs, and a key management bug could be devastating and unrecoverable. On the IT side, administrators I know have a different, equally frightening, set of problems with key management. Every IT manager I have spoken with has one or more of these questions: What happens if/when I lose keys? How to I back keys up securely? How do I replicate keys across multiple key servers for redundancy? I have 1,000 users reliant on public key cryptography, so how do I share these keys for all these users? If I expire and rotate keys, do I lose access to data archives? If I try to recover data from a tape, how do I get the right key? If I am using specialized key management hardware, how do I recover from fire or other disasters? All are risks in the minds of IT professionals every day. Lose your key, lose your data. Lose your data, lose your job. And that scares the heck out of people! Our goal in this section is to discuss key management options for database encryption. The introduction is meant to underscore the state of key management services today, and help illustrate why key management products are deployed the way they are. Yes, you can download excellent encryption tools for free, you can mix and match best of breed features, and you can develop your own operational key management process that is application agnostic, but this approach is becoming a rarity. And that’s a good thing because key management needs to performed by people who know what they are doing. Centralized, automated, embedded, pre-packaged and available as a complete service is the common choice. This removes the complexity and the responsibility of management, and much of the worry about reliability of your developers and IT administrators. Make no mistake, this trade-off comes at a price. Let’s dig into some key management practices for databases and how they are used. Internally Managed For database encryption, we define “internal key management” as key services within the database and provided by the database vendor. All of the relational database management platforms provide encryption packages, and included in these packages are key management functions. Typical services include key creation, storage, and retrieval, security; and most systems can handle symmetric and public key encryption options. Usage of the keys can be handled by proxy, as with the transparent encryption options, or through direct API calls to the database package. The keys are stored within the database, usually within a special table that resides in the administrative database or schema. Each vendor’s approach to securing keys varies significantly. Some vendors rely upon simple access controls tied to administrative accounts, some encrypt individuals’ keys with a single master key, while others do not allow any access to keys at all, and perform all key functions within a proxied service. If you are using transparent encryption options (see Part 2: Selection Process Overview for terminology definitions) provided by the database vendor, all key operations is performed on the users’ behalf. For example, when a query for data within an encrypted column is made, the database performs the typical authorization checks, and when successfully authorized, automatically decrypts the data for the users. Neither the users nor the application need be aware the data is encrypted, needs to make a specific request to decrypt, or needs to supply a decryption key to the database. It is all handled on their behalf, and often performed without their knowledge. Transparent key management’s greatest asset is just that: its transparency. The storage, management, security, sharing, and backup of the keys is handled by the database. With internally managed encryption keys, there is not a lot for the application to do, or even care about, since all