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What would you look for in a (X.509-) PKI solution, and why would you look for that, given the following constraints:

  • Available programming/sw-engineering know how is limited (ie, "OpenSSL with a handful of Perl scripts" is not a feasible approach)
  • Processes are reasonably well understood (eg certificate lifecycle)
  • Some (root/intermediate) certificates will have high monetary value and must be protected accordingly (HSM?)
  • Handle "a couple of tenthousand" identities across multiple organisations with delegated admin rights
  • Hardware-based solution (smartcard or otherwise) is likely to emerge as a requirement soon.
  • On-premises, self-hosted solution

I have identified some candidates from the "usual suspects", but I have some doubts (the market seems to have matured very little over the past years?). I will therefore not name the candidates but ask for unbiased inputs.

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Umm... First suggestion would be on your first point - Available technical know how is limited. If you're intending on supporting "a couple of tenthousand identities", and the other non-trivial requirements, you might want to get some expertise on board to do it right, not just select the right product. –  AviD Jan 27 '11 at 8:15
    
Good point, it's badly worded. This refers to programming/software-engineering skills; operational know how is not an issue. Will edit to clarify. –  Matthias Leisi Jan 27 '11 at 8:31
    
Are you looking to host on a Linux environment or a Windows environment? You say tying into smart cards... does that also include Active Directory integration? If so, the Certificate Services in Server 2008/R2 are pretty powerful. –  Steve Jan 27 '11 at 16:17

2 Answers 2

Full disclosure: I work for Voltage Security. I think it's better to state that up-front, rather than give you some sales spiel and then "accidentally" point you to our web site. While this is not a company-sponsored response in any way, I freely admit that my views are not unbiased. I will try to minimize the leakage into this response, but please read with the appropriate degree of skepticism.

The fundamental issue with asymmetric encryption schemes is not the encryption, but the key management. So what distinguishes PKI systems is not the security of the encryption, which is identical, but the ease of user provisioning, deletion, and general system management.

So, the questions I would ask of a vendor of asymmetric encryption are:

  1. What is the process for bringing a new recipient of encrypted data in to the system?
  2. How are the private keys stored, protected and backed up?
  3. How are credentials managed?
  4. How are name changes handled?(e.g. someone gets married and changes their name & system logon: what, if any, are the impacts?)
  5. How can encrypted data be scanned by data loss prevention devices to ensure insiders are not using the encryption facility as a way to smuggle data out of the company?

EDIT

(this is the stuff I left out originally, because it felt too sales-y)

Reasons for asking the questions above:

  1. Most PKI systems require the recipient to create a public / private key pair before any data can be sent to them. This inhibits ad-hoc use of the system, in which people can encrypt for any recipient.
  2. If a private key is lost, the data encrypted with the corresponding public key is lost. End of story. Any serious PKI system will have some mechanism for retrieving lost private keys. If this is a database of keys, then you need to think about how this is protected, and ensure that it is backed up frequently. Also consider replication if the solution has to exist in multiple data centers for high availability.
  3. This is a easy one: users have to provide some sort of authentication credentials to get access to the private keys. Ask how this can be integrated into existing authentication methods.
  4. Imagine that Mary Jones gets married (or divorced) and becomes Mary Smith. Using the credentials for "Mary Smith", she needs to be able to access data that had been previously encrypted for "Mary Jones". The PKI system should handle this case gracefully. The alternative is finding all the data encrypted for "Mary Jones", decrypting it and then re-encrypting it for "Mary Smith". Yuck.
  5. Fundamentally, the DLP device needs to be able to access the plaintext of any encrypted data. Ask how this can be achieved.
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1  
The disclosure part alone deserves an upvote for honesty, but so does the rest of your answer. Could I bother you to add a few more example reasons for asking each of the questions you describe, please? I have a good feeling you'd think of a lot better ones than I could, so I'd like to pick your brains a bit more while it's leaking goodies. Thanks! :) –  TildalWave Jun 6 '13 at 8:35

PKI is 5% technology, 95% procedures. The basic parts of X.509 certificates are exceedingly simple: that's just signatures. The first usable algorithms for that have been described in the late 1970s, and details had been mostly ironed out by the early 1990s (that's not to belittle cryptographic research of the last two decades, but in practice, PKCS#1 v1.5 signatures are good enough).

Procedures describe exactly what happens, preferably at "key stroke level": sensitive operations like renewal of an intermediate CA certificate ought to be performed by an operator under scrutiny of at least one auditor who checks that no key is pressed, no button clicked unless explicitly specified in the procedure. The scope is large; it also includes physical protections on the room which contains the CA, position of surveillance video cameras...

So the number one question that you must ask is: does the product comes with a comprehensive manual of procedures, or at least procedure templates to be adjusted to the local environment ? Writing these procedures and enforcing them is what will cost most in a PKI. This requires knowing what happens "under the hood": not a question of "programming how to" but more having clear and definite notions of what a private key is and what it can do. If you don't have this kind of knowledge in-house, and the PKI product does not come with enough information on that subject either, then you'll have to hire a consultant, and that's not cheap (I should know).


Authentication, Identity Management and Authorization are not the same thing. When we talk PKI in general, we often have in mind a number of requirements which relate to three distinct activities:

  • Identity Management: keeping track of users, their name, employee ID, date of last modification, and so on. This part is always needed but can be "implicit" or can be as simple as an Excel spreadsheet if there are only two dozen users. For 20k users, you will need something more evolved.

  • Authentication: making sure that someone purporting to be user U is indeed user U.

  • Authorization: knowing and keeping track of what operations a given user U is allowed to trigger, what data it can read and/or write.

These activities are distinct. Some products conflate some or all of them, and this can imply uncomfortable restrictions. For instance, consider Active Directory: as a LDAP server, it can be used for identity management, but its Kerberos component handles authentication; this makes it rather cumbersome to integrate non-password-based authentication with Active Directory.

The three kind of activities must be bridged, but still kept separate. X.509 certificates are mostly authentication, but issuance of certificates must feed on identity management in order to know what to put in certificates (a certificate binds a public key to an identity). A very important lesson about PKI is that certificates are no good for authorization. One of the first mistakes that most people do about PKI is that they try to embed access rights in certificates, and then it fails and they understand that they should not have done that (exact reason is hard to pin down but relates to the inherent asynchronism of certificate issuance).

So this brings a second question to ask to the vendor: does your product allow for separation of identity management, certificate management and authorization, and what bridges are supported between them ?

As an illustration -- not a product recommendation -- consider Microsoft Forefront Identity Manager, a suite which includes several products: FIM Service/Portal for identity management, FIM CM for certificates (a wrapper around a CA, also handles smart cards), FIM Synchronization for bridging identity management with AD servers and thus FIM CM,...


If your PKI has any serious value (and if not, why bother ?), then you will want to protect your CA private key(s) in a Hardware Security Module. Preferably, make the root CA offline, on the basis that an offline CA cannot be hacked in from the network. Distributing the root CA public key in all client systems is a major cost, and you don't want to do it twice, so you really really don't want to see your root CA compromised or lost or both.

Since you still have a lot of certificates to issue, you will probably need to have an online intermediate CA. You can recover from a loss or compromise of that CA without having to redistribute a new root CA key in all client systems (that's the point of separating the root from the intermediate CA), but that does not mean that you would be happy to see your intermediate CA private key stolen. So a HSM for that key would be great, too.

Therefore, ask your PKI vendor the following: are HSM supported ?

Smart cards are like small HSM, but on the client side. Smart card support requires some initialization; at some point, there will be some smart card specific code running on some desktop systems. There again, the PKI product may include some support for that, or not. Smart card vendors may also help.


If your certificates are for encryption, as opposed to signatures and authentication, then you will want some key escrow. Indeed, when some data is encrypted with a private key and the private key is lost, then the data is lost. Thus the need for a backup, somewhere. This is typically the case for encrypted emails. Such backups for keys are highly sensitive (they are a very tempting target for attackers) so they must not be improvised.

Thus: does the PKI solution includes a key escrow system ?

On the other hand, you certainly don't want to escrow keys used for signatures, because this will jeopardize any legal value that could be attached to these signatures (details vary depending on context and jurisdiction, but as a general rule you don't escrow signature keys). This implies that users who want to do encryption and signatures will need two keys, thus two certificates. Hence another question: does the PKI solution support multi-certificate users ?


All of the above is about PKI for X.509. Alternate solutions may exist, like ID-based cryptography (what "Voltage" is about, as linked to by @Dave), or decentralized systems like OpenPGP Web of Trust. A necessary initial step is to write down your requirements. You have the constraints; that's good. But you must also answer the following question: a PKI, yes, but to do what ?

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