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Problem processing SSL certificate response.

Author
21 Nov 2008 10:17 PM
Tyrven
Summary: When processing an SSL certificate response in IIS, a private key is
not generated with the certificate and, therefore, SSL does not function on
the site.  IIS and Certificates.mmc believe there is a private key, but when
I try to export one it fails with "The associated private key cannot be
found".  Details below.

In IIS's "Web Server Certificate Wizard" I am able to complete the "Process
the Pending Request" step as expected.  Afterwards, however, the website
properties do not allow me to "View Certificate".  If I return to the wizard
it acts as though I don't have a certificate.  If I choose "Assign an
existing certificate" and select the recently imported certificate, however,
then I am unable to connect to the site via HTTPS ("Internet Explorer cannot
display the webpage"). 

If I view the certificate in the MMC Certificates snap-in, I can see the
certificate.  If I open it, I am informed "You have a private key that
corresponds to this certificate".  When I try to export it, however, the
option to export the private key is disabled; the dialogue box notes: "The
associated private key cannot be found.  Only the certificate can be
exported." 

Clearly, the processing of the SSL certificate response is failing - but
why?  No error is provided when processing the response, nor does the event
log contain any relevent errors or warnings.  I've tried this with both
self-signed certificates as well as a GeoTrust-issued certificate; same
result. 

Note: This server contains a number of SSL sites.  I can use certificates
issued in the past or which have been imported (with private keys) from other
servers without a problem; the ports, router, bindings, etc are setup
properly.  Using a newly issued certificate, however, fails.  I could work
around this by requesting/processing the certificate on another server; as
this is our primary web server, however, I'd like to resolve the underlying
issue.

Tyrven

Author
22 Nov 2008 5:49 AM
David Wang
On Nov 21, 2:17 pm, Tyrven <Tyr***@discussions.microsoft.com> wrote:
Show quoteHide quote
> Summary: When processing an SSL certificate response in IIS, a private key is
> not generated with the certificate and, therefore, SSL does not function on
> the site.  IIS and Certificates.mmc believe there is a private key, but when
> I try to export one it fails with "The associated private key cannot be
> found".  Details below.
>
> In IIS's "Web Server Certificate Wizard" I am able to complete the "Process
> the Pending Request" step as expected.  Afterwards, however, the website
> properties do not allow me to "View Certificate".  If I return to the wizard
> it acts as though I don't have a certificate.  If I choose "Assign an
> existing certificate" and select the recently imported certificate, however,
> then I am unable to connect to the site via HTTPS ("Internet Explorer cannot
> display the webpage").  
>
> If I view the certificate in the MMC Certificates snap-in, I can see the
> certificate.  If I open it, I am informed "You have a private key that
> corresponds to this certificate".  When I try to export it, however, the
> option to export the private key is disabled; the dialogue box notes: "The
> associated private key cannot be found.  Only the certificate can be
> exported."  
>
> Clearly, the processing of the SSL certificate response is failing - but
> why?  No error is provided when processing the response, nor does the event
> log contain any relevent errors or warnings.  I've tried this with both
> self-signed certificates as well as a GeoTrust-issued certificate; same
> result.  
>
> Note: This server contains a number of SSL sites.  I can use certificates
> issued in the past or which have been imported (with private keys) from other
> servers without a problem; the ports, router, bindings, etc are setup
> properly.  Using a newly issued certificate, however, fails.  I could work
> around this by requesting/processing the certificate on another server; as
> this is our primary web server, however, I'd like to resolve the underlying
> issue.
>
> Tyrven


Download SSL Diagnostics 1.1 from Microsoft.com and use it to diagnose
and resolve your issue(s) with SSL.

It is not clear to me whether you are saying:
1. It is not possible to use IIS to Request/Process a certificate
request to enable SSL on a website.
2. OR it used to work on this IIS server but not any more.

It is also not clear to me whether you installed the SSL Certificate
in the LocalMachine's Personal store or not, nor if you installed the
SSL Certificate with or without "export" capability.


//David
http://w3-4u.blogspot.com
http://blogs.msdn.com/David.Wang
//
Author
22 Nov 2008 8:01 PM
Tyrven
David,

"Download SSL Diagnostics 1.1 from Microsoft.com and use it to diagnose
and resolve your issue(s) with SSL."

I know why SSL isn't working: there isn't a private key.  What I don't know
is WHY the private key isn't being generated by the "Process pending request"
option.

Note that I am able to work around this by requesting/processing a request
on a separate machine (my local Vista workstation, for example), then
transfering the generated PFX into the certificate store on the IIS machine. 
I can still use the Certificate Authority on the IIS machine to issue a
self-signed certificate.  The issue is exclusively with the ability of IIS to
process a certificate response.

> It is not clear to me whether you are saying:
> 1. It is not possible to use IIS to Request/Process a certificate
> request to enable SSL on a website.
> 2. OR it used to work on this IIS server but not any more.

Both statements are true.  The Request/Process wizard works fine (no errors)
but the result is an "orphaned" public key (no private key generated).  This
process worked up to six months ago (roughly); keys generated via IIS before
that are functional (but many are expiring); key generated (either new or
renewed) are orphaned.

> It is also not clear to me whether you installed the SSL Certificate
> in the LocalMachine's Personal store or not, nor if you installed the
> SSL Certificate with or without "export" capability.

When using the Request/Process wizard, these are not options.  The SSL
Certificate is automatically imported into the Local Machine ("My Computer")
Personal store with export capability.  I could manually import the
certifcate response from the Certificate Authority - but that wouldn't result
in processing a private key.

Hope this helps clarify the issue.

Tyrven
Author
23 Nov 2008 2:16 PM
David Wang
On Nov 22, 12:01 pm, Tyrven <Tyr***@discussions.microsoft.com> wrote:
Show quoteHide quote
> David,
>
> "Download SSL Diagnostics 1.1 from Microsoft.com and use it to diagnose
> and resolve your issue(s) with SSL."
>
> I know why SSL isn't working: there isn't a private key.  What I don't know
> is WHY the private key isn't being generated by the "Process pending request"
> option.
>
> Note that I am able to work around this by requesting/processing a request
> on a separate machine (my local Vista workstation, for example), then
> transfering the generated PFX into the certificate store on the IIS machine.  
> I can still use the Certificate Authority on the IIS machine to issue a
> self-signed certificate.  The issue is exclusively with the ability of IIS to
> process a certificate response.
>
> > It is not clear to me whether you are saying:
> > 1. It is not possible to use IIS to Request/Process a certificate
> > request to enable SSL on a website.
> > 2. OR it used to work on this IIS server but not any more.
>
> Both statements are true.  The Request/Process wizard works fine (no errors)
> but the result is an "orphaned" public key (no private key generated).  This
> process worked up to six months ago (roughly); keys generated via IIS before
> that are functional (but many are expiring); key generated (either new or
> renewed) are orphaned.
>
> > It is also not clear to me whether you installed the SSL Certificate
> > in the LocalMachine's Personal store or not, nor if you installed the
> > SSL Certificate with or without "export" capability.
>
> When using the Request/Process wizard, these are not options.  The SSL
> Certificate is automatically imported into the Local Machine ("My Computer")
> Personal store with export capability.  I could manually import the
> certifcate response from the Certificate Authority - but that wouldn't result
> in processing a private key.
>
> Hope this helps clarify the issue.
>
> Tyrven



Then, it looks like you should contact Microsoft PSS and open a
support case to determine the underlying issue in your situation.

You say that it worked before but not now, and you are confident that
you are doing the same actions as before that should work, and you
want to know why. Those requirements pretty much mean that you should
contact Microsoft PSS to open a support case because you believe a bug
was introduced.

I usually assign SSL Certificates in IIS in the way that you say still
works -- I never bother with the IIS Wizard to create/process requests
because I always keep track of the PFX certificate and explicitly
install the certificate on the server(s) of my choice with the options
of my choice. Going through the wizard is opposite of what I want,
especially when dealing with multiple servers in a farm.


//David
http://w3-4u.blogspot.com
http://blogs.msdn.com/David.Wang
//