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Struggling with Windows 2008 R2 PKI, Self-Signed Certificates & iPad View Client Secure Authentication To View Connection Server: UGH!

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Background: I was tasked to create an isolated VMware View test lab so that higher-ups could see how they could access dedicated VMs as well as how their developers could re-set linked clones on-the-fly. The project was successful! Yay!

 

Addendum: One boss wants to see how VMware View works when he accesses his dedicated VM via his iPad over the internet...And that needs a secure SSL connection.

 

The problem is: The domain name I offhandedly chose for the lab doesn't belong to me...So I can't get a real SSL certificate from a commercial Trusted CA.

 

So I'm trying to roll my own Windows 2008 R2 PKI and...While forcing that iPad to use the lab's DC/DNS server...Get that single iPad get trust the View Connection Server by importing some kind of certificate.

 

I can export/import a certificate from the Domain Controller CA to the iPad via an e-mail attachment...And it comes up as trusted. But how do I create a certificate from the View Connection Server and e-mail/import it into the iPad so it comes up as trusted? Every time I try to export the certificate from the View Connection Server's certificate store, e-mail it to the iPad, and install it...The Connection Server's certificate comes up as "untrusted" and the VMware View client will not connect.

 

(Granted, I could get sloppy and set the iPad Client to accept untrusted connections...But I want to solve the trusted connection issue.)

 

I might be royally missing something about self-signed certificates and certificate chains.

 

(This is a first time for me dealing with Windows Active Directory Certificate Services. In the past, I've always just installed expensive commercial CA SSL certificates in Windows Server certificate stores before.)

 

Whatever help or direction you can provide would be appreciated. I'm rather stumped.

 

Cheers!

 

Keegan


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