How not to improve the security of your ADFS deployment


I was involved in an ADFS deployment recently where the customer wanted to restrict access from the Internet to their ADFS proxy servers, located on their DMZ. They used ADFS to federate with Windows Azure Active Directory so they only wanted to allow traffic from the Microsoft Online Security Token Service (STS) servers into their ADFS. The rational behind this was that only a trusted party (Microsoft) should be able to communicate with an externally available service in their network. A good theory, but one doomed to failure. Let me explain why…

The WS-Federation Passive Requestor Profile

ADFS is Microsoft’s implementation of the OASIS group’s WS-* suite of protocols and mechanisms. A complete description of WS-*  is way beyond this post, but I will list some resources at the end of this post for the inquisitive among you. One of the purposes of the WS-* standard is to allow:

“different security realms to federate, such that authorized access to resources managed in one realm can be provided to security principals whose identities and attributes are managed in other realms”

In other words, to outsource authentication to somebody else that you trust.

The letters WS stand for Web Service, meaning that WS-* is created to work on the Internet, something e.g. Kerberos is not designed to do. Let’s look at a few pieces of WS-* terminology:

  • Requestor
    The client that wants access to some resource/content/service. Often a browser. Requestors are broadly split into two groups; those that can emit Web Service messages using SOAP and those that cannot. (Remember this last bit because it is important.)
  • Relying party (RP)
    The content provider that has something that a user wants access to. The RP has delegated the task of authentication to somebody else; the Identity Provider (IdP)/Security token Service (STS). The RP trusts the IdP/STS. In the Windows world an RP is often an IIS server with the Windows Identity Foundation (WIF) framework installed.
  • Identity Provider (IdP)
    A secure storage of identity information that also provides authentication mechanisms, allowing a Security Token Service (STS) to use it to authenticate. Active Directory is ADFS’ IdP.
  • Security Token Service (STS)
    A service that receives authentication requests from clients, authenticates them via its configured IdP, and issues tokens to clients, to be used at the RP.
  • Trust
    A relationship between the RP and the IdP/STS established with digital certificates whereby the RP trusts the IdP/STS.

A browser cannot emit web service requests, i.e. it cannot talk SOAP, so it uses something called the WS-Federation Passive Requestor Profile (PRP). WS-Federation is an extension to the WS-Trust specification that allows requestors that cannot talk SOAP to still exchange security information (tokens). They do this by being passive, meaning they rely on the RP and IdP to tell them what to do.

An implementation of this can look like this:


This is what happens when the passive requestor profile is used to obtain access to a resource:

  1. The requestor contacts the resource asking for access. The resource is the RP.
  2. The RP know the requestor’s security realm so it sends an HTTP redirect instructing the requestor to authenticate at its own realm.
  3. The requestor follows the redirect to its own realm where it is authenticated by its IdP/STS.
  4. In the request for authentication the requestor has included the URI of the resource it wants to access to. After the IdP/STS has authenticated the requestor, it sends another HTTP redirect back to the original resource. Included with the redirect is also a token, possession of which assures that the user has been authenticated.
  5. The requestor follows the redirect back to the original resource supplying the token and gains access to the resource.

The most important thing to note here is that when using the Passive Requestor Profile the RP and IdP/STS never need to communicate directly. It is only the requestor that needs to talk to all the involved parties.

Usually the RP is also an IdP/STS. In the case of Windows Azure Active Directory and federation with an on-premise Windows Server Active Directory the WAAD IdP/STS trusts your on-premise IdP/STS. This allows a single trust to be established. If not each RP would have to maintain its own trust with the IdP/STS.

So now that we know how the Passive Requestor Profile works how would this impact my customer’s request to only allow Microsoft’s STS to talk to its ADFS servers?


Answer is that it would break it and no one would be able to access any resource in the Microsoft cloud. As we have seen it is not the WAAD STS that communicates with on-premise ADFS, or the other way around, it is the requestors, i.e. the clients. So restricting access would deny every client access to on-premise ADFS, and thus any resource they want to access. Don’t do that.

Other stuff and more info

The customer had actually started working on this “security improvement” before I got involved and had already discovered IPs they needed to allow. For the curious, the name of the Microsoft STS is, which is a CNAME that resolves to the A record The A record has several records (I do not know if this is a complete list):


To restrict access and always use least privilege is a very good idea, in this case it just backfired because how the system works was not known.

If you want to know more about WS-*, ADFS etc., you can have a look at these resources:

Be secure!

New PowerShell module for Windows Azure Active Directory

A new version of the PowerShell module for Windows Azure Active Directory is available. This module was previously know as the Microsoft Online PowerShell module. The cmdlets all have the word MSOL in them, and the modules are called MSOnline and MSOnlineExtended. The version is still 1.0.0 as were the previous module. New in this release is support for Windows Server 2012; you can install the module on Windows Server 2012 and also configure the version of ADFS in Windows Server 2012. The documentation has also been updated.

Understanding X.509 digital certificate thumbprints


I got an interesting question about X.509 certificate thumbprints today from a colleague. Specifically, he wanted to know if you could renew a certificate and keep the thumbprint. The answer is no, unfortunately. So I thought I would explain why you can’t.

Certificate storage

The X.509 standard was first issued in 1988 and is described in several RFCs. It specifies, among other things, public key certificates, what we commonly refer to as X.509 certificates. X.509 certificates, in turn, currently come in three versions, v1, v2 and v3. The v3 certificates are described in RFC 5280. For the remainder of this post the terms certificate, public key certificate and X.509 certificate are used interchangeably.

X.509 certificates, as well as many other things in the X.509 standard, are described using Abstract Syntax Notation One (ASN.1). ASN.1 is a standard used to exchange information between systems independently of the systems’ encoding techniques. ASN.1 have several encoding rules:

  • Basic Encoding Rules (BER)
  • Canonical Encoding Rules (CER)
  • Distinguished Encoding Rules (DER)
  • XML Encoding Rules (XER)
  • Canonical XML Encoding Rules (CXER)
  • Extended XML Encoding Rules (E-XER)
  • Packed Encoding Rules (PER, unaligned: UPER, canonical: CPER)
  • Generic String Encoding Rules (GSER)

The original rules laid out for the ASN.1 standard were Basic Encoding Rules (BER), and CER and DER are more strict variants of BER. Digital certificates are usually stored in the file system as raw binary data, so DER (binary) is the most common. Certificates stored as raw binary usually have a .cer extension, but .der is also in use. Often the binary data is converted to Base64 ASCII files. This is called Privacy Enhanced Email (PEM), and these files commonly have one of these extensions: .pem, .crt, .cer, and .key.

Here is a screenshot of a DER encoded certificate opened in a HEX editor:


Here is the same cert encoded as Base64 also opened in a HEX editor:


Finally here is the same certificate in ASN.1 human readable form (this isn’t the whole cert):


So what does all this mean?

The RFC 5280 X.509 certificate definition

In RFC 5280 the basic syntax of a certificate (using ASN.1) defines three required fields:

Field Definition from RFC 5280
tbsCertificate The sequence TBSCertificate contains information associated with the subject of the certificate and the CA that issued it. Every TBSCertificate contains the names of the subject and issuer, a public key associated with the subject, a validity period, a version number, and a serial number; some MAY contain optional unique identifier fields.
signatureAlgorithm The signatureAlgorithm field contains the identifier for the cryptographic algorithm used by the CA to sign this certificate.
signatureValue The signatureValue field contains a digital signature computed upon the ASN.1 DER encoded tbsCertificate. The ASN.1 DER encoded tbsCertificate is used as the input to the signature function. This signature value is encoded as a BIT STRING and included in the signature field.

The tbsCertificate field is by far the largest containing also any extensions the certificate may have like key usage, alternate names etc. RFC 5280 lists all the possible extensions. signatureAlgorithm contains only one piece of data; the hashing algorithm used by the signing authority to sign this particular certificate. signatureValue contains the signature itself, calculated with the hashing algorithm from signatureAlgorithm.

The signature

To produce the certificate signature the signing authority takes the tbsCertificate field in ANS.1 DER encoded form (binary data) and applies the hashing algorithm to it. Inside the tbsCertificate field are some important fields. Specifically the subject name (CN), the hashing algorithm the signing authority used to sign the certificate and the subject’s public key. By signing all these fields the signing authority certifies that the subject in question does in fact own the public key in the certificate. It is a requirement that the signature field within the tbsCertificate field match the signatureAlgorithm field in the certificate. The important distinction here is that it is only the signature field inside the tbsCertificate field that is included in the signature, not the signatureAlgorithm field.

The Windows Cryptographic API

When a certain implementation uses the certificate it calculates and resolves a lot of information not included in the certificate itself. These are things like hash values of various fields and OIDs used to describe e.g. signing algorithms. Certificate Revocation checking is also usually performed and chaining and validation. One example of this behavior is the Windows CryptoAPI Cryptographic Shell Handler. This is the component that shows you a picture like the one below when you double click a certificate from Windows Explorer.



image Actual fields in the certificate
image Extensions in the certificate
image Computed fields not actually part of the certificate data

The certutuil.exe command line utility goes into even greater detail if you inspect (dump) a certificate:

X509 Certificate:
Version: 3
Serial Number: 6e9235460edbb5944d59f9f1a8f1cfe6
Signature Algorithm:
Algorithm ObjectId: sha1RSA (shaRSA)
Algorithm Parameters:
05 00
CN=Morgan Simonsen
Name Hash(sha1): 935093f16909002acd98626df485fa22b41d9dfd
Name Hash(md5): c32bdd1ad8eaf126fd96b2f7f23f2b9f

NotBefore: 16.04.2013 10:57
NotAfter: 01.01.2040 01:59

CN=Morgan Simonsen
Name Hash(sha1): 935093f16909002acd98626df485fa22b41d9dfd
Name Hash(md5): c32bdd1ad8eaf126fd96b2f7f23f2b9f

Public Key Algorithm:
Algorithm ObjectId: 1.2.840.113549.1.1.1 RSA (RSA_SIGN)
Algorithm Parameters:
05 00
Public Key Length: 2048 bits
Public Key: UnusedBits = 0
0000  30 82 01 0a 02 82 01 01  00 ac ed c3 1d 11 7f 63
0010  db 25 50 2e 9a c6 c1 f5  b7 23 c8 a0 71 a4 6e d6
0020  c8 29 17 8f 76 b6 8c 88  33 bf c9 0e 3d c8 0d 87
0030  11 60 e4 f0 77 ae e5 b4  47 6f b1 35 98 d3 44 d0
0040  52 c7 60 2e 7f e9 6c 3c  61 c2 36 3d a7 f5 32 88
0050  de 3c c4 79 62 91 b0 4b  24 78 a2 2e 6a 29 a9 ee
0060  0e 7a d8 0d 9e 12 7b b2  53 d1 17 8c 01 dc eb fb
0070  18 4d c0 ae df 61 7e 2b  dd 15 b5 65 b3 bc b9 25
0080  58 c9 ed 9e ef 9f 26 9b  79 c3 8e 13 92 9e 62 f3
0090  fe 8d ab 33 b4 40 a1 7b  0e b1 71 56 b4 9d 7b cb
00a0  61 9d 70 1d 9d b4 49 c9  46 42 fc 64 44 67 eb 8b
00b0  ea 7c 29 31 cb 4c 32 12  91 6c dd 04 59 07 51 6a
00c0  e6 40 fa ea 4e b2 ae 64  21 2e 6b 00 99 f0 7c 26
00d0  6e ad 6c 15 18 36 dc 81  61 e9 ce 28 7f f8 89 82
00e0  ee ed c5 ee 54 ee aa cd  01 72 75 71 59 fd fc cd
00f0  4d 53 3e 22 71 47 7f 24  e5 51 28 36 12 09 6b 0d
0100  af c9 37 9b e0 d1 00 67  11 02 03 01 00 01
Certificate Extensions: 1 Flags = 0, Length = 44
Authority Key Identifier
KeyID=b4 44 ec b5 97 5f 54 f8 ee e8 7b d0 1e c9 81 92
Certificate Issuer:
CN=Morgan Simonsen
Certificate SerialNumber=6e 92 35 46 0e db b5 94 4d 59 f9 f1 a8 f1 cf e6

Signature Algorithm:
Algorithm ObjectId: sha1RSA (shaRSA)
Algorithm Parameters:
05 00
Signature: UnusedBits=0
0000  8b 55 a5 5f f2 b3 2d 19  36 e9 9c cc 92 16 4e 62
0010  18 19 19 3e 7d 76 93 dd  04 9b 5e 0e b7 80 d7 38
0020  9d 1f b9 18 c3 6c 28 be  d6 64 a3 be 04 60 fc 63
0030  6d 26 dc 68 2b 3d c0 88  6d 36 22 a7 e7 c4 15 dc
0040  2b af 18 61 10 bb 3b 32  78 a6 36 08 81 29 b5 6a
0050  3e a2 2d c7 d0 31 69 1f  f3 fc 67 b7 df 2d e0 4e
0060  5d 37 ab a4 d1 56 e2 96  55 d7 21 d2 68 74 dc 5f
0070  b2 e5 12 54 e2 34 ae a0  08 9e 26 2f e2 4e 4e 98
0080  86 f7 6e ac ef e0 43 1e  0b 9d 59 3d a3 3d 55 03
0090  11 7c f1 df 00 1d 47 35  43 32 91 2a dc 4d 4b 9e
00a0  22 bf a1 f5 1e 1d ad d0  ee 73 34 99 43 82 5d 9e
00b0  b6 aa db 93 25 77 42 0a  bd d2 b2 9a e9 0e 31 2d
00c0  63 4c 4a 37 51 b4 b6 81  47 a8 94 fd e7 43 82 f7
00d0  ee 66 f1 d0 00 ff cf 9f  b0 a6 40 08 05 b8 ff 94
00e0  0b cd cf 50 e3 73 6a 03  2f 6f 95 8e 1b 51 e7 a7
00f0  ac ff 39 84 8c bf b8 65  41 c9 82 38 93 7c cb ab
Signature matches Public Key
Root Certificate: Subject matches Issuer
Key Id Hash(rfc-sha1): 91 cb 09 47 49 10 66 f1 fb 5b bc 8b 5e 0b b1 43 2c d8 80 b2
Key Id Hash(sha1): 4a eb 50 03 a3 78 80 bd 20 a0 00 da c6 f9 ef 8d cc 07 98 52
Key Id Hash(md5): 6a993e53bd40f8f69483d6da66f22a8f
Key Id Hash(sha256): 6979da8247c3080de96e861e9f000a22d6120170a3982bea4e9f054598f6453f
Cert Hash(md5): 94 08 89 bf 34 7e 17 2f 46 d6 25 49 f8 80 1f 6b
Cert Hash(sha1): 0b 61 2f 71 4b 8d ef d5 59 2b d4 5d a9 fe 8c c5 bb ba 36 48
Cert Hash(sha256): 52c93aa9bd509f8b375e0ec8340d9219bac4386497b521d8a7b800eda22e850c
Signature Hash: dee3cb948ffb745c3047e4f393bcf9144863b733
CertUtil: -dump command completed successfully.


The Thumbprint

As you can see from the output of the Crypto Shell Extension and Certutil.exe the thumbprint is a computed field, i.e. not a part of the certificate data itself. In the GUI these are called Properties. In the shell extension the thumbprint is called thumbprint and in the Certutil output it is called Cert hash. From this we can surmise that the thumbprint is some kind of hash or one way function (OWF), whose friendly name is thumbprint. (The fact that the shell extension actually has a field called Thumbprint algorithm also helps.) Certutil is also kind enough to compute both a SHA1 and an MD5 hash for us, while the GUI will only do SHA1. As far as I can tell Windows always uses SHA1 to calculate the thumbprint hash, regardless of which signature algorithm is used in the certificate itself.

So what is the thumbprint a hash of? Turns out it is actually the whole certificate, i.e. the binary data representing the three required fields (tbsCertificate, signatureAlgorithm and signature). You can verify this by using a tool that can generate hashes directly from the certificate binary DER file in the file system. In the screenshot below I have used the HashCheck Shell Extension. This tool has a nice feature where you can paste a hash you have obtained from somewhere and see if it matches any of the computed hashes for the file. Here I have copied the thumbprint hash value from Certutil and pasted into the tool:


Since the thumbprint is a hash of the certificate in binary DER encoding this will not work if your certificate is stored in any other format than DER.


So now we have the answer to why you cannot request a new certificate, or renew an existing one, with the same thumbprint. Changing anything in the certificate data will produce a completely different hash result and thus a completely different thumbprint.

The thumbprints purpose is actually to make it easy to locate a particular certificate in the certificate store of a system. Let’s say you have a webserver that needs a certificate. Instead of specifying a certificate by subject name, validity or anything else you just supply the thumbprint to the webserver.

More information

To write this post I created a self signed certificate with my name as the subject. The command I used was this:

makecert.exe -pe -n “CN=Morgan Simonsen” -ss My -r morgan_simonsen.der

You can download all the various versions of the certificate from this post from the following link if you want to look in more detail and compare with what I have written.

There are four files in the archive:

File Format
morgan_simonsen.der Binary DER format
morgan_simonsen.crt PEM (Base64) format
morgan_simonsen.asn Raw ASN.1 ASCII data
morgan_simonsen.txt Certutil –dump –asn of the DER cert


Norwegian content: How to integrate your on-premise Active Directory with Windows Azure Active Directory

I have published a 5 part blog series on the Norwegian Microsoft TechNet Blog, with step by step instructions for setting up integration between your on-premise Window Server Active Directory Directory Service and Windows Azure Active Directory. It covers concepts, single-sign on with ADFS, Directory Synchronization with the DirSync Tool and troubleshooting. So if you speak my native language; head on over: