Tag Archives: CryptoAPI

Advanced Troubleshooting of Certificate Validation Related Problems on Windows Part 2

One of the most complicated things to troubleshoot in X.509 is failures related to Name Constraints handling, there are a few ways to approach this but one of the easiest is to use the Extended Error Information in the Certificate viewer.

Lets walk through an exercise so you can try using this on your own, first download this script, if you extract its contents and run makepki.bat you get a multi-level PKI that looks something like this:


Before we begin its useful to understand that Name Constraints are applied at an Issuing CA level, in this case the constraints say that the CA is authoritative for any DNS or RFC822 name within in the example.com domain, it also allows a specific base distinguished name (DN).

In our example these constraints are applied by the “Test Partner CA” on to the “Customer CA”; you can see the restrictions in its certificate:


This script creates two certificates, one for email (user.cer) and another for SSL (www.cer), normally the script makes both of these certificates fall within the example.com domain space but for the purpose of this post I have modified the openssl.cfg to put the email certificate in the acme.com domain. — The idea here is that since this domain is not included in the constraints a RFC 3280 compliant chain engine will reject it and we have an error to diagnose.

Normally we don’t already know what the failure associated with a certificate chain is, after all that’s why we are debugging it but the process we use here will help us figure out the answer — applications are notorious for sharing why a certificate chain was rejected.

Since we can’t rely on the applications one way for us to figure this out on our own is to look at the chain outside of the application in the Windows Certificate viewer to see if we can tell what the issue is there.

Let’s start by looking at the “good” certificate:


What’s important here is that we see no errors, but how do we know that? Well let’s look at the bad certificate and see what the difference is:


The certificate clearly has a problem and Windows has done a decent job of telling us what the problem was, there is a name in this certificate that is inconsistent with the Name Constraints associated with this certificate chain. The question is — which name?

To answer that question we need to look at the Name Constraints, remember that this is in the CA certificates it can be in any or all of them which means we need to first figure out where the Constraints are.

To do that we start at the “Certification Path”, here you see something like this:


Notice the little yellow flag, that’s the certificate viewer saying this is where the problem is, let’s take a look at that certificate:


But wait! There isn’t a problem with this one, that’s because this certificate is actually good it’s the certificate it issued that is the problem. Here is the non-obvious part, let’s look at the details tab:


Here we see Windows is telling us exactly what the problem was with the certificate that this CA has issued, it is the email address and its inclusion of the acme.com domain.

Remember that it was restricted, via the Name Constraints extension, to the example.com domain when issuing email certificates. The chain engine would be non-compliant with the associated RFC if it trusted this certificate.

But why did we see this Extended Error Information in this certificate and not the leaf itself? This is actually by design and makes sense when you think about it. Name Constraints can exist in each issuing CA certificate in the chain and what is happening here is that CryptoAPI is telling us that the issuer certificate that was flagged is the offending actor.

This Extended Error Information is available in the Certificate Viewer in a number of cases (for example Revocation), though most of the interesting cases require the application to launch the certificate viewer as you get to view the certificate chain (and all of the associated state) that they were using when they encountered the problem.

Advanced Troubleshooting of Certificate Validation Related Problems on Windows Part 1

The Windows platform for validating X.509 certificates has a feature I don’t see many discuss — its robust logging subsystem.

This allows a non-developer (and developers) to get insights into what is happening with applications interactions with CryptoAPI 2 and to some degree what is happening inside those APIs.

To use this feature you must first enable it, the easiest way to do that is via the EventViewer Management Console (eventvwr.msc), once in there you must navigate to the CryptoAPI 2 (CAPI2) node of the viewer:

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Once you get there you select Properties on the operational log, which will give you a dialog that looks something like this:



Once you “Enable Logging” and “Apply” the changes, immediately all calls to CryptoAPI will be logged. CryptoAPI is used all the time so by the time you close that dialog you will have some events you can look at:



The high level view of each event doesn’t tell you much, for example in the above picture we really only know that the action that was being performed with a “Build Chain”, this particular event corresponds to a call to CertGetCertificateChain.

To really understand what is going on you need to look at the Details tab:



Here we can see what was passed into a given into that API call, we can see what certificates we passed in by the calling application, what settings they chose when making that call:



Some other things you can see in this particular API call include what the disposition of the call was and of course what certificate chain was built.

Every major API in CryptoAPI has logging similar to this, you get to see what is passed in and what came out. Additionally major “objects” are sometimes logged as well, for example here is an event showing a certificate that CryptoAPI was operating against:



Another very useful API to be able to look at is CertVerifyRevocation, this will be logged in this fashion:



Some of these events include references to temporary files, for example in this case you see:


This is a CRL for the “GlobalSign PersonalSign 1 CA – G2”, its stored in the Time Valid Object Cahce (TvoCache), you can look at this cache with the “certutil –urlcache” command.


The events will all tell you which application was the caller and if they are part of a sequence of tasks you get enough information to correlate them and put them in order.



I won’t go through all of the events but as you can see this is super valuable when trying to figure out – Why did that application do that?!

As you might imagine this logging can slow things down and produces a bunch of data so be sure to turn it off when you are done.

Understanding Windows Automatic Root Update

Windows has a feature called Automatic Root Update, when CryptoAPI does a chain build, exhausts the locally installed root certificates it downloads (if it has not already done so) a list of certificates it should trust.

This list contains attributes about those certificates (hashes of their subject name and keys, what Microsoft believes it should be trusted for, etc.).

If it finds the certificate it needs in that list it downloads it and installs it.

So how does this technically work?

There is a pre-configured location where Windows looks for this Certificate Trust List (CTL), it is http://www.download.windowsupdate.com/msdownload/update/v3/static/trustedr/en/authrootstl.cab.

NOTE: Technically they do use different language codes in the URLs based on the client local but to the best of my knowledge they all map to the same files today.

This list is downloaded and de-compressed; you can do the same thing on Windows (with curl) like this:

mkdir authroot

cd authroot

curl http://www.download.windowsupdate.com/msdownload/update/v3/static/trustedr/en/authrootstl.cab>authrootstl.cab

expand authrootstl.cab .\authroot.stl

You can open authroot.stl with explorer and look at some of its contents but for the purpose of our exercise that won’t be necessary.

This file is a signed PKCS #7 file, Windows expects this to be signed with key material they own (and protect dearly).

It contains a Microsoft specific ContentInfo structure for CTLs and a few special attributes. WinCrypt.h has the OIDs for these special attributes defined in it but for brevity sake here are the ones you will need for this file: OID_CTL OID_ROOT_LIST_SIGNER OID_CERT_PROP_ID_METAEKUS CERT_FRIENDLY_NAME_PROP_ID OID_CERT_KEY_IDENTIFIER_PROP_ID OID_CERT_SUBJECT_NAME_MD5_HASH_PROP_ID CERT_ROOT_PROGRAM_CERT_POLICIES_PROP_ID OID_CERT_PROP_ID_PREFIX_98 OID_CERT_PROP_ID_PREFIX_105 szOID_ENROLL_CERTTYPE_EXTENSION szOID_CERTSRV_CA_VERSION OID_ROOT_PROGRAM_FLAGS_BITSTRING

Copy this list of OIDs and constants into a file called authroot.oids and put it where we extracted the STL file.

We can now use the following OpenSSL command to inspect the contents in more detail:

openssl asn1parse -oid authrootstl.oids -in authroot.stl -inform DER

There is lots of stuff in here, but for this exercise we will just download the certificates referenced in this list.

To do that we need to understand which of the attributes are used to construct the URL we will use to download the actual certificate.

This list values we want are just after the OID_ROOT_LIST_SIGNER, the first one being “CDD4EEAE6000AC7F40C3802C171E30148030C072”, its entry will look like this:


  128:d=8  hl=2 l=  20 prim:         OCTET STRING      [HEX DUMP]:CDD4EEAE6000AC7F40C3802C171E30148030C072

  150:d=8  hl=3 l= 246 cons:         SET

  153:d=9  hl=2 l=  30 cons:          SEQUENCE

  155:d=10 hl=2 l=  10 prim:           OBJECT            :OID_CERT_PROP_ID_PREFIX_105

  167:d=10 hl=2 l=  16 cons:           SET

  169:d=11 hl=2 l=  14 prim:            OCTET STRING      [HEX DUMP]:300C060A2B0601040182373C0302

  185:d=9  hl=2 l=  32 cons:          SEQUENCE

  187:d=10 hl=2 l=  10 prim:           OBJECT            :OID_CERT_SUBJECT_NAME_MD5_HASH_PROP_ID

  199:d=10 hl=2 l=  18 cons:           SET

  201:d=11 hl=2 l=  16 prim:            OCTET STRING      [HEX DUMP]:F0C402F0404EA9ADBF25A03DDF2CA6FA

  219:d=9  hl=2 l=  36 cons:          SEQUENCE

  221:d=10 hl=2 l=  10 prim:           OBJECT            :OID_CERT_KEY_IDENTIFIER_PROP_ID

  233:d=10 hl=2 l=  22 cons:           SET

  235:d=11 hl=2 l=  20 prim:            OCTET STRING      [HEX DUMP]:0EAC826040562797E52513FC2AE10A539559E4A4

  257:d=9  hl=2 l=  48 cons:          SEQUENCE

  259:d=10 hl=2 l=  10 prim:           OBJECT            :OID_CERT_PROP_ID_PREFIX_98

  271:d=10 hl=2 l=  34 cons:           SET

  273:d=11 hl=2 l=  32 prim:            OCTET STRING      [HEX DUMP]:885DE64C340E3EA70658F01E1145F957FCDA27AABEEA1AB9FAA9FDB0102D4077

  307:d=9  hl=2 l=  90 cons:          SEQUENCE

  309:d=10 hl=2 l=  10 prim:           OBJECT            :CERT_FRIENDLY_NAME_PROP_ID

  321:d=10 hl=2 l=  76 cons:           SET

  323:d=11 hl=2 l=  74 prim:            OCTET STRING      [HEX DUMP]:4D006900630072006F0073006F0066007400200052006F006F007400200043006500720074006900660069006300610074006500200041007500740068006F0072006900740079000000

We can download this certificate with the following command:

curl http://www.download.windowsupdate.com/msdownload/update/v3/static/trustedr/en/CDD4EEAE6000AC7F40C3802C171E30148030C072.crt> CDD4EEAE6000AC7F40C3802C171E30148030C072.crt

If we look at the contents of the certificate we can see this is the 4096 bit “Microsoft Root Certificate Authority”.

The next in the list is 245C97DF7514E7CF2DF8BE72AE957B9E04741E85, and then the next is 18F7C1FCC3090203FD5BAA2F861A754976C8DD25 and so forth.

We could go through and parse the ASN.1 to get these values, iterate on them and download them all if we wanted. Of course if we wanted to get all of the root certificates we might as well just download the most recent root update here: http://www.microsoft.com/en-us/download/details.aspx?id=29434

It contains the same information just in a self-contained format (this is whats used by down-level clients that do not have Automatic Root Update).

Anyhow hopefully this will be useful for someone,


CryptoAPI, Revocation checking, OCSP and the Unknown certStatus

In CryptoAPI one can use the CertGetCertificateChain API to do the path building and basic chain validation, this validation may include revocation checking depending on which flags you pass via dwFlags; for example these flags control if revocation checking occurs, and if so, on which certificates:


Typically you would specify CERT_CHAIN_REVOCATION_CHECK_CHAIN_EXCLUDE_ROOT which ensures the whole chain is checked (where possible – e.g. one shouldn’t bother asking the root if he considers himself revoked).

But in the context of OCSP what are the potential revocation related returns we might see?

  1. Revoked – I have received a signed response from the CA or have had policy pushed to me that tells me that this certificate is not to be trusted.
  2. Not Revoked – I have received a signed response from the CA that says this certificate was not revoked.
  3. Unknown – I have received signed response from the CA that says it doesn’t know anything about this certificate.
  4. Offline – I was unable to reach the responder to verify the status of the certificate.

Each of these cases are clearly represented in the API that is used by CertGetCertificateChain to perform the revocation check, this API is CertVerifyRevocation. The higher level CertGetCertificateChain however only has two possible returns: Revoked and Unknown outside the “not revoked” case.

One might assume the OCSP Unknown would get mapped into the Revoked state, this unfortunately is not the case, it is returned as unknown, as does the Offline error.

This means that if OCSP was used you cannot tell what the actual status was, this is especially problematic since IE and Chrome both default to modes where they ignore “Unknown” revocations due to concerns over Revocation responder performance and reliability.

It is possible to work around this platform behavior though — the problem is that it’s not documented anywhere, let’s take a quick stab at doing that here.

First since CertGetCertificateChain doesn’t tell us what method was used to do revocation checking we have to use heuristics to figure it out. Thankfully to enable OCSP stapling in higher level protocols like TLS the OCSP response is passed back to the caller if OCSP was used; to get that we need to know:

1. The CERT_CHAIN_ELEMENT in the returned CHAIN_CONTEXT points to the following revocation information:

  • PCERT_REVOCATION_INFO pRevocationInfo;
  • PCCRL_CONTEXT           pBaseCrlContext;

2. For an OCSP response, the CRL_CONTEXT is specially created to contain the full OCSP response in the following critical extension szOID_PKIX_OCSP_BASIC_SIGNED_RESPONSE.

  • The presence of this extension indicates an OCSP response was used.
  • The Issuer name in the CRL is the name of the OCSP signer.
  • The signature algorithm is sha1NoSign.
  • ThisUpdate and NextUpdate contain the response validity period.

With this we can take the OCSP response from the CRL_CONTEXT and then look at the “ResponseData” within it, you will need to look within the “responses” here,  you will need to find the right “SingleResponse” based on its “CertID”.

NOTE: Some responders will return the status of multiple certificates in a response even if the status of only one was requested.

You now can determine what the responder said the status of the certificate was by inspecting “certStatus” element.

This is a fair amount of work unfortunately but it does enable you to do the right thing with authoritative “Unknown” responses.