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Cygwin with OpenSSL for CSR generation

A lot of services, which are published to the Internet, are secured with SSL certificates. A lot of times we use SSL certificates to secure communications when implementing ISA reverse proxy servers, Citrix Secure Gateway servers and/or Cisco WebVPN portals.

When you want to secure a connection with a SSL certificate you have to create a Certificate Signing Request (CSR) and get the CSR signed by a Certificate Authority (CA). This can be done by a “real” CA, like GeoTrust or Verisign, or you can configure your own CA and sign your own CSR.

There are a lot of ways for generating CSR’s. In first I always used what the customers could offer me. This could be the Cisco ASA firewall, a Windows server with IIS or the Juniper SA appliance. Sometimes could take a couple of hours before I could finally generate a CSR. While generating a CSR, a private key is also generated. When using customer equipment for generating the CSR, it could happen that the customer deletes the private key, which makes the CSR useless.

A colleague of mine often has the same problems and he started using Cygwin with OpenSSL under Windows. I have to say, GREAT. I started using it myself. A great advantage is that I can use my own laptop and I don’t have to depend on the customers equipments. Furthermore, and maybe the most important, I know what I am doing during the generation and signing of certificates, so I will never delete the wrong files.

Normally I generate a new private key per certificate and I use the following commands for generating the private key, CSR and the actual certificate.

1. Generate a private key
openssl.exe genrsa -out private-www-booches-nl.key 2048

2. Generate the CSR, fill in the required information (common name is the most important)
openssl.exe req -sha256 -new -key private-www-booches-nl.key -out csr-www-booches-nl.csr

3. The CSR is uploaded to the CA. The CA sends you the SSL certificate, which I save as www-booches-nl.crt

4. Create the actual SSL certificate
openssl.exe pkcs12 -export -out www-booches-nl.pfx -inkey private-www-booches-nl.key -in www-booches-nl.crt

When using an Open Source web server you have to use a certificate with a DER format. The first 3 steps, as shown above, are still the same. You can use the following steps to create a DER file.

4. Put the key file code at the end of the crt file
cat private-www-booches-nl.key >> www-booches-nl.crt

5. Create the DER file
openssl.exe x509 -in www-booches-nl.crt -inform PEM -out www-booches-nl.der -outform DER

It is also possible that you need a PEM certificate instead of a PFX certificate. Below you see the command to create a PEM certificate from a PFX certificate.

6. Create the PEM file
openssl.exe pkcs12 -in www-booches-nl.pfx -out www-booches-nl.pem -nodes

7. Check the CSR content
openssl.exe req -text -noout -in

Using Cygwin with OpenSSL really makes it easier when working with CSR’s and certificates. A very usefull website with “The Most Common OpenSSL Commands” can be found here (in Dutch).

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René Jorissen

Co-owner and Solution Specialist at 4IP Solutions
René Jorissen works as Solution Specialist for 4IP in the Netherlands. Network Infrastructures are the primary focus. René works with equipment of multiple vendors, like Cisco, Aruba Networks, FortiNet, HP Networking, Juniper Networks, RSA SecurID, AeroHive, Microsoft and many more. René is Aruba Mobility First Expert (AMFX #26), Aruba Certified Mobility Expert (ACMX #438), Aruba Certified ClearPass Expert (ACCX #725), Aruba Certified Design Expert (ACDX #760), CCNP R&S, FCNSP and Certified Ethical Hacker (CEF) certified. You can follow René on Twitter and LinkedIn.

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