Setup Failed To Generate The Ssl Keys Vmware

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Setup failed to generate the SSL keys necessary to run VMwar 安装好后提示这个又回滚回去了。. Apr 10, 2014  This is a multi part video series to compliment the white paper on Deploying a Centralized VMware vCenter Single Sign-On Server with a Network Load Balancer. Hi there, currently running a horizon environment, with one security server in dmz and 2 connection servers – version 7.2. I wanted to upgrade the environment – switchting to UAG Server 3.8 in the DMZ and 2 new 7.11 servers with latest windows os.

If you want to convert your website from HTTP to HTTPS, you need to get a SSL certificate from a valid organization like Verisign or Thawte. You can also generate self signed SSL certificate for testing purpose.

In this article, let us review how to generate private key file (server.key), certificate signing request file (server.csr) and webserver certificate file (server.crt) that can be used on Apache server with mod_ssl.

Key, CSR and CRT File Naming Convention

I typically like to name the files with the domain name of the HTTPS URL that will be using this certificate. This makes it easier to identify and maintain.

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  • Instead of server.key, I use www.thegeekstuff.com.key
  • Instead of server.csr, I use www.thegeekstuff.com.csr
  • Instead of server.crt, I use www.thegeekstuff.com.crt

1. Generate Private Key on the Server Running Apache + mod_ssl

First, generate a private key on the Linux server that runs Apache webserver using openssl command as shown below.

The generated private key looks like the following.

2. Generate a Certificate Signing Request (CSR)

Using the key generate above, you should generate a certificate request file (csr) using openssl as shown below.

3. Generate a Self-Signed SSL Certificate

For testing purpose, you can generate a self-signed SSL certificate that is valid for 1 year using openssl command as shown below.


You can use this method to generate Apache SSL Key, CSR and CRT file in most of the Linux, Unix systems including Ubuntu, Debian, CentOS, Fedora and Red Hat.

Setup Failed To Generate The Ssl Keys Vmware

4. Get a Valid Trial SSL Certificate (Optional)

Instead of signing it youself, you can also generate a valid trial SSL certificate from thawte. i.e Before spending the money on purchasing a certificate, you can also get a valid fully functional 21 day trial SSL certificates from Thawte. Once this valid certificate works, you can either decide to purchase it from Thawte or any other SSL signing organization.

This step is optional and not really required. For testing purpose, you can always use the self-signed certificate that was generated from the above step.

Go to Thwate trial certificate request page and do the following:

Setup Failed To Generate The Ssl Keys Vmware
  • Select “SSL Web Server Certificate (All servers)” under the “select your trial certificate”.
  • Do not check the PKCS #7 check-box under the “configure certificate”
  • Copy/Paste the *.csr file that you generate above in the textbox under “certificate signing request (CSR)”
  • Click on next at the bottom, which will give you a 21-day free trial certificate.


Copy/Paste the trial certificate to the www.thegeekstuff.com.crt file as shown below.

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Setup Failed To Generate The Ssl Keys Vmware Server

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Your company's security policy might require that you replace the default ESXi SSL certificate with a trusted certificate on each host. You can also regenerate a self-signed certificate and key if the default certificate and key were accidentally deleted.

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Setup Failed To Generate The Ssl Keys Vmware Server

SSL certificates are used to vouch for the identity of the components involved in the communication and to secure communication between vSphere components.

By default, vSphere components use the self-signed certificate and key that are created during installation. Self-signed certificates are as secure as certificates that are issued by an external Certificate Authority as long as the user validates the certificate and its thumbprint when the warning dialog appears.

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Replace self-signed certificates with certificates from a trusted CA, either a commercial CA or an organizational CA, if company policy requires it. Consider also replacing certificates to avoid having users get used to clicking through browser warnings. The warning might be an indication of a man-in-the-middle attack, and only inspection of the certificate and thumbprint can guard against such attacks.

You can replace the default certificates with trusted certificates in a number of ways.

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If you accidentally deleted the default self-signed certificate and key or you changed the host name, you can generate a new self-signed certificate and key from the ESXi Shell. See Generate New Self-Signed Certificates for ESXi.