IMPORTANT: This post is being kept for archival purposes, but please reference http://technet.microsoft.com/en-us/library/cc707697(TechNet.10).aspx for official documentation on how to get this configured.

After my original post on configuring ISA bridging with ConfigMgr 2007, I've had several conversations with both the ISA team and customers and have been able to work out a different way to configure bridging with ConfigMgr 2007. This is still a complicated solution with some overhead, but I think that folks will find this much more palatable than the original solution.

Pre-Requisites 

Here's what you'll need in advance to any further ISA configuration:

1. A Microsoft Enterprise CA. I have not been able to get this to work with a Standalone CA and don't know if this is possible. I'd love to be proven wrong, though.
   
2. A web server certificate on the ISA server. If you're using a single Internet MP, the subject name or subject alternate name(s) in this certificate has to match what you're using in the ConfigMgr console for the external FQDN. For the purposes of this post, I performed this configuration with a single MP/DP combination. If you're using multiple MPs and DPs for IBCM, you'll have to have multiple subject alternate names in the certificate adding additional complexity to the rules. ISA 2006 supports multiple subject alternate names (with caveats), ISA 2004 doesn't support this at all.
3. A client certificate on the ISA server, this certificate needs to be in the Personal store for the Microsoft Firewall service account (fwsrv). This certificate is used by ISA to authenticate itself with the management point when bridging the SSL connections
4. Your ISA server needs to be domain joined because it needs a means to authenticate ConfigMgr client certificates. It can be joined to a private domain in the DMZ, it does not have to be a corporate domain.

CA Configuration Specifics

I cloned the Authenticated Session template and created a new one. For the purposes of this example, I called it "IBCM Client Authentication". In the Request Handling tab for the template, I have "Allow private key to be exported" checked, and "Enroll subject without requiring any user input checked." I don't know if these are required or not. In the Subject Name tab, I have "Supply in the request" selected as we will need to specify custom certificate names. For "Extensions" make sure that "Application Policies" has "Client Authentication" as the only policy.

Client Configuration Specifics 

Clients will need to have client authentication certificates using the "IBCM Client Authentication" template. The subject name format has to be "machinename$@addomainfqdn". The AD domain FQDN has to be the same AD domain as the ISA server. The machine name has to be a Computer in the AD site that ISA is joined to. For my proof of concept, I put these machines into a special group that wasn't Domain Computers. The client computer itself does not have to be joined to the domain, and in fact, I did my proof of concept with workgroup clients. There just has to be a computer account in AD that maches machinename in the certificate.

Sample configuration: AD domain is "contoso.com", client machine name is "myclient". Certificate subject has to be "myclient$@contoso.com". MYCLIENT has to be a Computer account in AD. You absolutely have to provision this certificate from the template that extends Authenticated Session or else this won't work, and this is why I couldn't get this to work with a Standalone CA.

ISA Configuration Specifics 

When configuring the web listener for the server publishing rule on the ISA server, you'll need to use a certificate for that listener to connect back to the management point. This is the certificate I mentioned in #1 above. For the listener, you'll need to choose "SSL Client Certificate Authentication" and have it point to Active Directory. Unfortunately, this will end up adding complexity to the configuration, but this is absolutely necessary for security! I'll talk more about why later. For authentication delegation, you'll want to use "No delegation, but client may authenticate directly" (I believe this is only needed in ISA 2006, not 2004).

If you want to restrict the paths that the rule will respond to, you'll need at minimum /sms_mp/*, /ccm_incoming/*, /ccm_outgoing/*, and /ccm_system/*. Other features (software update points, for example) may require additional paths. It's important to note that fallback status points (FSPs) do not use SSL, so you'll need to have the rule accept non-SSL requests, or set up a separate server publishing rule for your FSP. If you're using a FSP, you'll need to also allow /sms_fsp/*.

For the properties of the actual bridging rule, you'll want to go to the "Bridging" tab, and select "Use a certificate to authenticate to the SSL Web server." For this certificate, you'll want to use the client certificate mentioned in #2 above. The server publishing wizard doesn't do this for you, so this will require an additional manual step after running the wizard.

Summary

While this isn't a "simple" solution, it has considerably less overhead and complexity than the original certificate mapping-based solution. Instead of having to gather the certificates, and bind them to an AD user account using certificate mapping. All you need to do is create a specifically formatted certificate, and make sure it maps to a computer account in AD. I've done a couple of successful lab deployments with this so far and have been happy with the results. Please let me know if you have any questions or other comments and I'll be happy to try to address them.

If after reading this and you still have questions, you can request documentation from the ISA Server team. Please send an e-mail jointly to isadocs@microsoft.com and smsdocs@microsoft.com. 

Update: I've attached a sample .INF file to this posting. 

It's a pretty commonly asked question. People want to use different subject names on the Internet and intranet for their MPs. This isn't hard to do, and it requires something called a Subject Alternative Name, often abbreviated as SAN. The SAN can contain multiple alternate names. The SAN will take precedent over the common name (CN), or the regular subject name for a certificate. This is important because it means that if you have "hostnameA" in the CN, and "hostnameB" in the SAN, "hostnameA" will cause a CN mismatch. You will have to have a SAN for "hostnameA" and "hostnameB" for both to work.

To request certificates with SANs, you have to first configure your CA to support them. On Microsoft CAs, SAN support is not enabled for general requests by default. To enable this, run the following command on your CA server: certutil.exe -setreg policy\editflags +EDITF_ATTRIBUTESUBJECTALTNAME2

You MUST restart Certificate Services after doing this.

Now that the CA is configured to support SANs, you need to specially craft your request to use them. If going through web enrollment, you can add a custom attribute in the last section. To specify a SAN of "hostnameA" and "hostnameB", you would use the following syntax: SAN:dns=hostnameA&dns=hostnameB

Each SAN argument is ampersand separated. This should issue a certificate that will have a "Subject Alternative Name" section under Details. You can verify this by using the browser test by going to each https URL and ensuring that you don't get any certificate errors.

If you're using an .INF file to request certificates from a CA, the syntax is slightly different. You'll need to add a [RequestAttributes] section, and then use the syntax of: SAN="dns=hostnameA&hostnameB"

Hopefully this will be enough to help provide some basic knowledge on how to configure SAN support on the CA and in certificates.

I proctored two labs yesterday around migrating sites from mixed mode to native mode. I talked to a lot of people and tried to answer a lot of questions. There were a few common threads, which I will elaborate here because I found them interesting.

Native mode is hard

Native mode setup is something I pretty much take for granted. I've been setting up native mode sites since June of 2006, so it's all pretty much second nature to me. The certificate authority setup and requirements, provisioning certificates, and so on. But, seeing people struggling through the labs brought me back to reality. Native mode has a lot of dependencies and complicated configuration steps required outside of the product for it to work. Unfortunately, there's not a lot we as a product team can do around that. One of the decisions we made was to be agnostic to PKI environments. We just use the certificates that we are given (provided they are in our basic set of parameters). One of the reasons this was done was because in the "real world", most companies would have completely separate people as their "SMS guy" and "PKI guy", so the "SMS guy" would give his or her requirements to the "PKI guy", who in turn would provide the requisite certificates.

People are really interested in Internet Based Client Management

I'd say 80% of the questions that were asked of me were about Internet Based Client Management. Things such as basic requirements, different modes, how it works in big hierarchies, and most of all, ISA configuration. I think a lot more people are interested in IBCM than we may have originally estimated, and there's a lot of questions about it. I pretty much figured this was the case given how the forums have been lighting up with questions around it, but hearing it from people out in the field further validates that. 

ISA setup with ConfigMgr was a very hot topic. I'm going to prioritize my postings here to make my next post specifically on ISA bridging as that was definitely up in there as a "most asked" class of questions.

Overall, it was a great experience going to TechReady and talking with people out in the field. It's always great working with customers, and those who work with customers, and I hope in my future postings here, I can answer some of the common questions people have had about native mode and IBCM.

Let's jump right in to one of the most complicated, and frankly, confusing aspects about Internet Based Client Management (IBCM), and that's how to use it with firewalls. I'm going to focus on its use with ISA server, because that's what I have the most experience using. Because IBCM requires native mode, and this requires SSL, it presents some interesting challenges and configurations required for firewalls.

When creating the necessary server rules for IBCM using ISA, there's two options: SSL bridging (sometimes called SSL termination or server publishing), or SSL tunneling. Both have their own strengths and weaknesses.

SSL Tunneling: tunneling is the most simple means of getting traffic through a firewall to your management point and distribution point from the Internet. In essence, it's simply brokering traffic from point A to point B. It is very fast as it's just passing bits around. However, you cannot perform any traffic inspection or use any advanced firewall features because all it's doing is shifting encrypted blobs around. It doesn't know or care about what's in the data, it just wants to move data.

SSL Bridging: bridging is the most complicated, but also the most secure means of getting traffic through a firewall to your management point and distribution point from the Internet. It requires a certificate on its end, and the client actually uses the SSL bridge as its "management point". The SSL bridge decrypts the traffic, performs any inspection on it, and then re-encrypts it with its own certificate, and passes it to the actual management point. This obviously can have a very large performance penalty as you're doubling the encryption and decryption required. This is also very complicated to set up since you have to double your certificates.

For comparison, here's a couple pictures I made a while back for a presentation that showed the comparitive differences between the two:

SSL tunneling:

SSL bridging:

Those images put into perspective what the different modes are doing and what they mean to IBCM.

In Part 2, I will discuss the finer points of actually configuring ISA for use with Configuration Manager with some sample configurations.