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How to Request/Apply New SSL Certificate in IIS 6 for Windows 2003

Posted on 2013-06-19
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Last Modified: 2013-06-20
We are currently running IIS 6.0 on Windows 2003 Server with Exchange 2003 for the purpose of accessing our emails via our smartphones and/or OWA.  It's recently been brought to my attention that our SSL certificate expired on 6/15/13.  I was told by our IT consultant that it'd be easiest to request a new certificate then to renew it.  I'm finding plenty of information on how to request a brand new certificate or renew an existing certificate, but I'm not certain about how to proceed if there's already an expired cert. in place.

At this point, I haven't heard of users not being able to access emails on their phones, but we do have some data collectors that our surveyors out in the field use that aren't.  My best guess is that I should choose to remove the current certificate while in the IIS Certificate Wizard, but wanted to confirm to help minimize potential downtime.

Thanks in advanced!
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Question by:blugirl
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by:IKtech
ID: 39260889
what company did you buy the cert from?  If you call them and buy a new one, they will walk you through the request and then the install from iis.
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by:IKtech
ID: 39260894
don't worry about removal until you have the new one installed and you are using it.
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by:blugirl
ID: 39260911
@IKtech - I'm not certain who the original company was as it was purchased by our consultant several years ago.  When I view the expired Certificate, it says it was issued by "Starfield Secure Certification Authority".  For consolidation purposes, I considered just purchasing it through SiteGround since that's where our domain is being managed & our website hosted.  But when I asked them about the steps, this was their response:

"Please note, that we cannot assist you with the installation of the SSL on your external server, once it has been issued."

and...

"You can have your network support assistant help you with the issuance of the CSR, and after that you can hand it to us so that we issue the SSL certificate from our vendor."

SG's support is usually fantastic & I understand that they have to draw the line on how much support to give...so I'm assuming that any other CA would say the same?
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by:blugirl
ID: 39260964
@IKtech - I was told by our network support consultant that I needed to generate the CSR (Certificate Signing Request) request from our IIS server first. Is that not the case?
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IKtech earned 500 total points
ID: 39260995
That is correct i would make a cert request on the server from the IIS manager.  Once you have purchased the cert you will give the CSR (which is a text file) to the company that you bought the cert from and they will use it to produce a cert for you.  

Hope fully that makes sense.

I know you didn't buy the cert from digicert but their help docs should help a little

CSR creation
http://www.digicert.com/csr-creation-microsoft-outlook-web-access.htm

Install cert
http://www.digicert.com/ssl-certificate-installation-microsoft-iis-5-6.htm

this company also will try to help you with the above if you need it.
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Author Comment

by:blugirl
ID: 39263661
@IKtech, I just went ahead & proceeded with ordering a new cert from DigiCert.  They were fantastic!  Great support, super knowledgeable & walked me right through it all!  Thanks for the tips!
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Author Closing Comment

by:blugirl
ID: 39263672
The solution for me was simply to go through DigiCert!  They were super fast, friendly, knowledgeable & patient.  They made a potentially intimidating process easy!!
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by:IKtech
ID: 39263962
Great, glad to hear it!!
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