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Managing SSL Certificates for Virtual Machines: A Guide by Dave Funk, EITC 2011

In this guide by Dave Funk, learn about effectively managing SSL certificates, keys, and CSRs for server VMs. The ease of creating VMs can lead to situations where previous configurations are lost, including important SSL components. Discover a method to package OpenSSL certificates for import into Microsoft servers, covering the steps to create CSRs, sign certificates, and convert them into PKCS#12 files. This approach enhances SSL management outside of VMs and ensures secure operations within your server environment.

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Managing SSL Certificates for Virtual Machines: A Guide by Dave Funk, EITC 2011

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  1. SSL certs for server VMs Dave Funk EITC, October 2011 EITC 2011, @Penn State

  2. VMs are great, but… Easy to create, too easy to recreate EITC 2011, @Penn State

  3. VMs are great but … • Easy to create, too easy to recreate • When recreating a VM need to remember to save previous configs, including SSL keys/csrs • Wouldn’t it be nice to be able to manage SSL keys/certs/csrs outside VMs EITC 2011, @Penn State

  4. Trick to package up OpenSSL Apachie style cert for importation into Microsoft server. • Can package cert, key, and intermediate certs. EITC 2011, @Penn State

  5. 1) create CSR & key as normal, get it signed. • 2) take signed .pem cert, put in file • 3) post-pend encrypted key after cert, • 4) post-pend intermediate CA-cert .pem after key. • 5) convert to pkcs12 ".p12" file: EITC 2011, @Penn State

  6. openssl pkcs12 -export -in cert+key+intermediate.pem -passin pass:key-password -passout pass:package-password -out certificate-file.p12 -name friendly-name • where: • cert+key+intermediate.pem == file created by steps 1-4 above • key-password == password for encrypted key • package-password == password to encrypt whole .p12, then used as 'Import password' for IIS • friendly-name == "friendly" name to be displayed by IIS cert manager window for this cert • order of contents in .pem file important, host-cert first, then matching key, finally any necessary intermediate certs. EITC 2011, @Penn State

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