This article will explain and demonstrate the techniques that will add custom extensions to certificate requests.

A little abstract. As you know, when Hewlett-Packard iLO generate certificate request for SSL it include server *short* name to the Subject field. There is no way to change subject name format. While output request file is signed you cannot edit this request, because signature will become broken and CA (Certification Authority) will reject this request. Subject name short format is not quite useful, because many administrators prefer FQDN (Fully Qualified Domain Name), for example: iLO1.domain.com. I agree with this point that FQDN are more useful and can be used in various network configurations and in multi-domain/multi-forest environments.

Continuing my previous post I want to discuss about certificate installation. As you know, certificate erollment generally consist of several steps:

• Certificate Request generation;
• Certificate Request submission to Certification Authority;
• Certificate Request response (certificate signed by CA) installation;

In previous post I have demonstrated how certificate request can be created using native PowerShell capabilities. While CA server cannot be contacted directly from managed client, you will have to manually transfer and submit certificate to Certification Authority.

When you create Certificate Request, it is placed in Certificate Enrollment Requests container (in Certificates snap-in). This request waits for signed certificate public part. When certificate public part is signed by external authority, signed certificate must be installed to local store. Installation process consist of two steps:

I would like to demonstrate a quite pretty script that simplifies certificate request generation for OpsMgr managed clients. Recently we had have to use various complex (for administrators that are not familiar with digital certificates) methods, such:

• CertReq.exe utility in conjunction with Policy.inf file (as decribed here: Certificate Enrollment for System Center Operations Manager Agent);
• Request generation using MMC console Certificates snap-in.

Both methods require some additional steps to generate request. For example, if you use CertReq.exe utility you need to write enough complex certificate enrollment configuration file. If you use Certificates snap-in you will need to manually specify all necesary data (such subject, private key settings, certificate extensions, etc). This PowerShell script will do all stuff, so you will have to copy and paste script to PowerShell console and run it.

This post is based on existing OpsMgr product group (PG) post: Troubleshooting Ops Mgr Certificate issues with Powershell. For me existing script return overloaded information to user and is not quite easy for understanding. Also there is missing some points:

• certificates might be issued from 3rd party Certification Authorities (CAs) and not always has SerialNumber fixed length. Therefore in some cases it incorrectly converts certificate serial number to it actual value;
• by default X509Chain.Build() method (for Operating Systems prior Windows 7/Server 2008 R2) by default attempts to build a chain up to any root certificate that is stored in Trusted Root CAs container in CurrentUser store. This means that while original script return "Ok" status, OpsMgr Agent may not work with this certificate, because root certificate don't exist in Trusted Root CAs in LocalMachine store;

Another point is that what we want to get from script? I thing that we just want to know: