The Nightmare that is PKI and Digital Certificates


Identity Verification
Identity Verification

Digital certificates support three main functions. The first is to provide a container for your public and your private key. If you want to purchase a digital certificate, the issuer will send you a digital certificate with both the public and the private key on it. So what do we do with this? Well if we have encrypted some data with the private key, we must send the recipient our public key, so the second usage is to strip-off the public key and add it to a digital certificate which is sent to the recipient, who can use it to decrypt the encrypted message. The third usage is related, but has a different function. For this the digital certificate is used to identity an object, such as the sender of a message. In this way the sender signs something in the message with their private key, and then distributes the public key with the certificate, and the recipient gets the signature and can verify the send.

Certificate store
Certificate store

It can be quite cumbersome to send the digital certificate each time we want to prove our identity or to decrypt some encrypted data, so we normally store our certificate in a repository, so that it can be used again (otherwise we can add keys to a key ring). This is either on the local machine, or can be stored on a trusted certificate repository. The screen shot on the right-hand side shows an example of my certificates, where I have stored the certificates for,, and so on. Once I accept these certificates, they are then trusted on subsequent visits. It is thus important that users check these certificates when they are first accessed, so that they are checked for their credibility. Unfortunately most users do not check them, and can end-up with certificates which a malicious or, at least, do not provide the right level of verification. For high-risk accesses, such as to your bank or for e-commerce applications, you need to be sure that the certificate has credibility with you.

As we will find the key elements of a digital certificate are: the issuer, the serial number, the date when it is valid from and to, and the public and private keys. If you trust the issuer to make checks on the entity, then you can trust the certificate which has been signed by them. An understanding of who can issue certificates, and the checks that they make is thus important. I sign many PDFs for student references with a self-signed digital certificate … which has absolutely no credibility at all … but the little padlock at the bottom of the PDF looks good though. Basically I have signed it myself, to say that I am me, but anyone else can do the same.

So what about Bob and Alice (and Eve)?

It is possible for Bob to sign a message with his private key, and that this is then decrypted by Alice with her public key? There are many ways that Alice could get Bob’s public key, but a major worry for her is that who does she trust to receive his public key? One way would be for Bob to post his public key on his web site, but what happens if the web site is down, or if it is a fake web site that Alice uses. Also if Alice asked Bob for his public key by email, how does she really know that Bob is the one who is responding? Thus we need a method to pass public keys, in the verifiable way. One of the best ways is to provide a digital certificate which contains, amongst other things, the public key of the entity which is being authenticated. Obviously anyone could generate one of these certificates, so there are two ways we can create trust. One is to setup a server on our own network which provides the digital certificates for the users and devices within an organization, or we could generate the digital certificate from a trusted source, such as from well-known Certificate Authorities (CAs), such as Verisign, GlobalSign Root, Entrust and Microsoft. These are generated by trusted parties and which has their own electronic thumbprint to verify the creator, and thus can be trusted by the recipient, or not. If you want to understand how digital certificates are created, I setup a link for you to create your own certificate:

PKI and Trust

ExampleThe major problem that we now have is how to determine if the certificate we get for Bob is creditable, and can be trusted. The method used for this is to setup a PKI (Public Key Infrastructure), where certificates are generated by a trusted root CA (Certificate Authority), which is trusted by both parties. As seen in Figure 1, Bob asks the root CA for a certificate, for which the CA must check his identity, after which, if validated, they will grant Bob a certificate. This certificate is digitally signed with the private key of the CA, so that the public key of the CA can be used to check the validity of it. In most cases, the CA’s certificate is installed as a default as a Trusted Root Certificate on the machine, and is used to validate all other certificate issued by them. Thus when Bob sends his certificate to Alice, she checks the creditability of it (Figure 2), and if she trusts the CA, she will accept it. Unfortunately, the system is not perfect, and there is a lack of checking of identities from CA, and Eve could thus request a certificate, and be granted one (Figure 3). The other method is to use a self-signed certificate, which has no creditability at all, as anyone can produce a self-signed certificate, as there is no validation of it. An example of this is shown on the right-hand side, where a certificate has been issued to Bill Buchan (even though the user is Bill Buchanan).

cert02Figure 1 Getting a certificate

cert03Figure 2 Alice checks the certificate

cert04Figure 3 Eve spoofs Bob

cert06Thus our trusted root CA, which we will call Trent, is trusted by both Bob and Alice, but at what level of trust? Can we trust the certificate for authenticating emails, or can we trust it for making secure network connections? Also, can we trust it to digital sign software components? It would be too large a job to get every entity signed by Trent (the root authority), so we introduce Bert, who is trusted by Trent to sign on his behalf for certain things, such as that Bert issues the certificate for email signing and nothing else. Thus we get the concept of an intermediate authority, which is trusted to sign certain applications (Figure 4), such as for documentation authentication, code signing, client authentication, user authentication, and so on.

Note that there are typically two digital certificates in use. The one that is created by the CA that has both the private and public key on it (and can be stored on a USB stick, so that the encryption keys can be recovered at any time), and there is one that is distributed which does not have the private key (for obvious reasons).

cert07Figure 4 Trusted root CA, intermediate CA and self-signed

Digital certificate types

Typical digital certificate types are:

  • IKE.
  • PKCS #7.
  • PKCS #10.
  • RSA signatures.
  • X.509v3 certificates. These are exchanged at the start of a conversion to authenticate each device.

A key factor in integrated security is the usage of digital certificates, and are a way of distributing the public key of the entity. The file used is typically in the form of X.509 certificate files. Figure 5 and Figure 6 shows an example export process to a CER file, while Figure 7 shows the actual certificate. The standard output is in a binary format, but a Base-64 conversion can be used as an easy way to export/import on a wide range of systems, such as for the following:


The CER file format is useful in importing and exporting single certificates, while other formats such as the Cryptographic Message Syntax Standard – PCKS #7 Certificates (.P7B), and Personal Information Exchange – PKCS #12 (.PFX, .P12) can be used to transfer more than one certificate. The main information for a distributable certificate will thus be:

  • The entity’s public key (Public key).
  • The issuer’s name (Issuer).
  • The serial number (Serial number).
  • Start date of certificate (Valid from).
  • End date of certificate (Valid to).
  • The subject (Subject).
  • CRL Distribution Points (CRL Distribution Points).
  • Authority Information (Authority Information Access). This will be shown when the recipient is prompted to access the certificate, or not.
  • Thumbprint algorithm (Thumbprint algorithm). This might be MD5, SHA1, and so on.
  • Thumbprint (Thumbprint).

The certificate, itself, can then be trusted to verify a host of applications (Figure 4.20), such for:

  • Server authentication.
  • Client authentication.
  • Code signing.
  • Secure email.
  • Time stamping.
  • IP security.
  • Windows hardware driver verification.
  • Windows OEM System component verification.
  • Smart card logon.
  • Document signing.

cert08Figure 5 Exporting digital certificates

cert09Figure 6 Exporting digital certificates


Figure 7 Digital certificate

cert11Figure 8 Options for signing

So what’s the problem?

Fake or real?
Fake or real?

The theory of creating a public and private key using RSA is sound, and this has proven to be secure (although the number of bits required to keep it secure increases by the day). Unfortunately few people actually know how it works. So, to test you, ask yourself these questions:

  • When was the last time that you checked the credibility of the bank you are visiting?
  • When was the last time you accepted a certificate, even though it had problems?
  • Would you know where to go in a browser to find the details of a certificate, and could you actually interpret them correct?
  • Do you know how your software components on your system are verified for their credibility, and that they can from their original source?
  • Do you know who the most creditably signers of certificates are? Is Google a signer? Is GlobalSign a signer?

If the answer to any of these is “I don’t know”, we have problems the PKI, as it should be there to, unfortunately, protect the end user, but obviously it isn’t.

Unfortunately many people when faced with a certificate will not actually know if the CA is a credible one, or not, and this is the main weakness of the PKI/digital certificate system. There are many cases of self-signed certificate, and of certificates which are not valid, faking the user.


There is a demonstration of digital certificates at:

If you’re interesting in methods of authentication, please view:

16 thoughts on “The Nightmare that is PKI and Digital Certificates

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