Vmware Server Failed To Generate Ssl Keys

1. Vmware Server Failed To Generate Ssl Keys In Windows 7
2. Vmware Server Failed To Generate Ssl Keys In Windows 10
3. Vmware Server 2.0 Setup Failed To Generate The Ssl Keys
4. Vmware Server Failed To Generate Ssl Keys

I’ve seen quite a few VMware environments where when you login, you get that silly error message about a certificate not being trusted. This is something we can fix and more importantly be sure that the connections are trusted and encrypted.

• Trusted root certificates deployed to workstations – Instructions for Lab Environment
• Web-Certificate Template Deployed – Instructions for Lab Environment
• Certificate Authority Web Enrollment server – (If you followed the Lab Environment setup this should be on your CA already)
• Download OpenSSL and install it. I used 1.01h as the version for my lab which worked fine on a Server 2012 R2 Server which is also my vCenter Server.
• Download and install the vCenter Certificate Automation Tool from VMware. This is also found in the vCenter install media for vSphere 5.5.

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I prefer to create my certificate requests right from the VMware vCenter Server, so I install both the SSL Automation Tool and OpenSSL directly on the vCenter Server. If you’re using the VMware vCenter Server Appliance you’ll need to do this someplace else and there are some additional steps not listed in this post. Please see this KB article for more info: vCSA SSL Certs

You can run the SSL-Updater tool by double clicking the batch file in the directory where you unzipped the tools. Look for ssl-updater.bat. Note: it might be useful to run this as Administrator if UAC is on.

When you run the SSL Tool, you’ll get a menu with options. To begin with you should select option 1. This option will explain the steps that need to be done and the order in which to do them.

When you select option 1, you’ll be presented with a new menu. This menu asks what you’re going to update. If you are going to do all of the services listed, look for option 8. You can see from the screenshot that the steps will be listed. You should copy that list to a text file or something to recall it later.

Assuming you didn’t copy the list, and that the tool isn’t modified too much, you can use the list below.

1. Go to the machine with Single Sign-On installed and – Update the Single Sign-On SSL certificate.

2. Go to the machine with Inventory Service installed and – Update Inventory Service trust to Single Sign-On.

3. Go to the machine with Inventory Service installed and – Update the Inventory Service SSL certificate.

4. Go to the machine with vCenter Server installed and – Update vCenter Server trust to Single Sign-On.

5. Go to the machine with vCenter Server installed and – Update the vCenter Server SSL certificate.

6. Go to the machine with vCenter Server installed and – Update vCenter Server trust to Inventory Service.

7. Go to the machine with Inventory Service installed and – Update the Inventory Service trust to vCenter Server.

8. Go to the machine with vCenter Orchestrator installed and – Update vCenter Orchestrator trust to Single Sign-On.

9. Go to the machine with vCenter Orchestrator installed and – Update vCenter Orchestrator trust to vCenter Server.

10. Go to the machine with vCenter Orchestrator installed and – Update the vCenter Orchestrator SSL certificate.

11. Go to the machine with vSphere Web Client installed and – Update vSphere Web Client trust to Single Sign-On.

12. Go to the machine with vSphere Web Client installed and – Update vSphere Web Client trust to Inventory Service.

13. Go to the machine with vSphere Web Client installed and – Update vSphere Web Client trust to vCenter Server.

14. Go to the machine with vSphere Web Client installed and – Update the vSphere Web Client SSL certificate.

15. Go to the machine with Log Browser installed and – Update the Log Browser trust to Single Sign-On.

16. Go to the machine with Log Browser installed and – Update the Log Browser SSL certificate.

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17. Go to the machine with vSphere Update Manager installed and – Update the vSphere Update Manager SSL certificate.

18. Go to the machine with vSphere Update Manager installed and – Update vSphere Update Manager trust to vCenter Server.

From the Automation Tool, we can now select option 2 which is the generate certificate signing requests. From here, we’ll need to select the service that we are creating a request for. No, you can’ t do them all at once

Select the service, and answer the questions. You’ll need to know things like IP Addresses, DNS Names, Locations and a file location to export the requests and private keys.

When the process is done, you’ll see three files in the file location you specified. Next, repeat this process for the rest of the services that you want to sign.

Once these files have been created, you can take the certificate signing requests and upload them to the Certificate Authority to obtain the certificate. You should be able to do this by going to https://NAMEOFCA/certsrv/default.asp assuming you followed the prior posts about setting up a Certificate Authority for your home lab.

Vmware Server Failed To Generate Ssl Keys In Windows 7

Once here, choose “Request a Certificate”.

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Choose “Advanced Certificate Request”.

Choose the base-64-encoded option.

Now you need to take the rui.csr file and copy the entire contents into the web page request box. Choose the VMware-SSL certificate template (or any other Web Template you have created).

Choose the Base64 encoded option and then click the “Download Certificate”.

Save the file as rui.crt in the same directory as where the request came from. This needs to be the same one that the Automation Tool created them in for the later steps to work correctly. Once this is done, repeat the process for each of the services you are going to request SSL certificates for.

Once you’ve requested all of the certificates, go back to the default CA page and click the “Download a CA certificate, certificate chain, or CRL” link.

Here we will download the RootCA. Choose Base64 and select the appropriate CA Certificate from the list. Then click “Download CA certificate chain” link.

Now, save this file as “cachain.p7b” and I usually do this in the parent directory of the services I’m requesting. I don’t think this one matters too much.

Once exported, you need to open the cachain.p7b file, and export it.

Export the file.

When prompted, select the Base-64 encoded X.509 (.CER) option.

Save the file as Root64.cer

Now we need to open the rui.crt files for each of the services that we now have certificates for and paste the contents of the Root64.cer certificate to the end of the file. From the screenshot below, you can see my SSO Service rui.crt file has the Root64.cer file appended to the end.

Save the file as chain.pem in the service folder. Don’t forget to do this same thing for each of the services you’ve requested.

Whew! I know there are quite a few steps here, but I assure you that the hard parts are over. In the next post, we’ll show you how to replace the default certificates in vCenter with the new certificates that you’ve created. We’re almost there.

VMware is a software company dealing in the cloud and virtualization software and services, situated in America. Wide ranges of products are developed by VMware, which includes desktop software, server software, cloud management software, application platform, and backup software and so on. Products offered by VMware are easily adapted by Microsoft Windows, Linux, and Mac OS X.

VMware server is the dynamic product which can create virtual machines and it runs on Windows OS and Linux. In this article, we will see how to install SSL certificate on VMware Server.

Obtain the SSL certificate

There are two ways of obtaining the SSL certificate: Creating a self-signed and another is purchasing the Certificate from trusted third-party vendor (Certificate Authority).

Among these, the Self-Signed Certificate is not recommended as it cannot protect your server from being eavesdropped by intruders.

Purchase an SSL certificate from the Certificate Authority (CA). Some of world famous Certificate Authorities are Symantec, GeoTrust, RapidSSL, Comodo, GlobalSign, AlphaSSL, and Thawte.

Choosing the appropriate certificate

Varieties of certificates are issued by the CAs for different security needs. SSL certificates can be categorized mainly into three categories:

• Single Server Name Certificate: This will secure and confirm the identity of a single server for e.g.: www.test.com. For those using single View Connection Server instance or those providing access to users to View Environment with a single URL, this type of certificate should be appropriate.
• Subject Alternative Names (SAN): SAN certificates will be useful to those who need to secure more than one server names along with the single certificate. For e.g.: www.test.com can be used for www.test-first.com
• Wildcard SSL certificates: Wildcard SSL certificates are named so because they add a wildcard character “*” before the name of the domain/server. Wildcard certificate will secure multiple servers. Also new additions to can be secured with the Wildcard certificate. For example, a certificate for, *.abc.com will secure test.abc.com.

Creating a Certificate Signing Request (CSR)

In order to get an SSL certificate issued, you will need to generate a config file and a CSR from the config file and send it to the CA. When the CA sends the certificate, you need to import the signed SSL certificate and store it into View Server host where the private key is stored.

There are multiple ways of generating the CSR depending on the generation of the certificate.

For Windows Server 2008 R2, Microsoft certreq is the tool used for generating the CSR and importing a signed certificate.

1. Create a Certificate Signing Request Config fileThe Microsoft certreq tool will use a config file in order to create a CSR. Following is the process of creating a CSR config file; Paste the following code in a text editor along with the beginning and ending tags:
2. Change the attributes of the subject with relevant values for the View Server and deployment. Some of the CAs may restrict the use of the abbreviations for the ‘State’ attribute.
3. Updating the key length attribute. This step is optional.Normally the value of the key length is 2048 until and unless you have special requirements. The larger the key, the more is the security but also, can downgrade the performance.
4. Name the file as request.inf and save it.

Requesting the signed Certificate

With the help of config file, generate the CSR with the certreq tool. Send this as a request to a third party CA.

Process:

1. First of all, open a command prompt in the Start menu and choose Run as administrator.
2. Go to the directory where the request.inf file is saved.
3. Create the CSR file. For e.g.: certreq –new request.inf certreq.txt
4. From text editor open the CSR file and copy all the contents, including the beginning and end tags. Something like:

5. Now use the contents of the CSR file for certificate request made to the CA by complying the enrollment procedure. After some verification process, CA will sign the request and will send an encrypted private key along with the certificate.

6. Save the certificate in a text file with the name of cert.cer on the View server.
7. CA will send root and intermediate CA certificates. Save the root CA certificate with the name of root.cer and intermediate CA certificates with intermediate.cer.

Importing the Certificate

You can use the certreq tool as well as some other method to import the certificate.

While using the certreq tool, the private key is local because it is on the server on which the CSR was generated.

If you want to use another method, then you can use the Microsoft Management Console (MMC) Snap-in in order to import the certificates.

Process:

1. Go to the command prompt and choose Run as administrator.
2. Go to the directory where the cert.cer file is saved.
3. Run the certreq-accept commands to import the certificate.

After this, you are ready to use the certificate on your server.

Integrating the imported certificate for the View Server

After importing following steps should be taken to integrate the SSL certificate on View Server:

1. Cross check the imported certificate.
2. Name the certificate as vdm.
3. Root and intermediate CA certificates need to be installed.
4. View Connection Server Service, secure server service or View Composer service needs to be restarted to let the View Service use SSL certificates.

Converting the Certificate File

Vmware Server Failed To Generate Ssl Keys In Windows 10

If the private key and obtained certificate are in PEM or any other format, you will be required to convert it into PKCS#12 (PFX) format.

Vmware Server 2.0 Setup Failed To Generate The Ssl Keys

Helpful Resource:

Vmware Server Failed To Generate Ssl Keys

• If you do not have OpenSSL, you will need to install it. For installing OpenSSL, you can download it from the OpenSSL official website.
• Once SSL certificate installation process has been completed, you should use our SSL checker tool to find out configuration issues.