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New SDDC Certificate Replacement Fling

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Certificate lifecycle management is not something anyone looks forward to, it is time consuming and usually not automated. However, it is a necessity for many of our customers. The process gets even more challenging when needing replace certificates across multiple VMware products, not only careful orchestration but also properly reestablishing trust between product just adds another layer of operational complexity. Within the Integrated System Business Unit (ISBU) at VMware, which produces both the VMware Validated Design (VVD) and VMware Cloud Foundation (VCF), the team has been working on a way to simplify certificate management, not only for individual products (working with product teams) but also holistically at the VMware SDDC level.

This initially started with the development of a tool called Certificate Generation Utility (CertGen), which helps customers generate new certificates for various products within the VMware SDDC. Although it was developed for the VVD, any VMware customer who consumed products within the VVD, could also leverage this tool. We all know certificate generation can be a pain, but it is not as challenging or as complex as the actual certificate replacement process itself which is also fully documented by the VVD team here.

This is where the new Fling comes in, the SDDC Certificate Tool, which automates the manual steps outlined by the VVD and helps customers easily replace certificates that they have created (CertGen or another process) and automatically orchestrates this across the different products within the SDDC. The tool is command-line driven and uses a JSON configuration file which can contain all or a subset of the VMware SDDC products, which is great for supporting different environments and allows for easy source control. Extensive pre-checks are also built into the tool to validate the certificates themselves (e.g. expiry, chain validation, etc) also also preventing miss-match of information (e.g. SAN entries, number of nodes, etc) which then get compared against your actual environment before any changes are applied. The JSON also contains a section referred to as Service Accounts, which is merely other VMware product accounts that the tool supports to reestablish trust after replacing the certificate for given product. 

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PowerCLI script to help correlate vCenter, ESXi & vSAN build/versions w/o manual VMware KB lookup

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I can still remember when I was a VI Admin and how annoying it was to try to correlate the build numbers for my ESX(i) hosts and vCenter Servers that I have deployed with the versions listed on VMware's website. This especially gets challenging when there are multiple patch releases (a, b, c or 01, 02, 03) in between major releases (5.5, 6.0, 6.0u1, 6.0u2, 6.5, etc.). Historically, most customers including myself would retrieve the respective build numbers and then manually comparing them to either the release notes and/or download website which was very tedious.

Although VMware has exposed the version number within our vSphere products since day 1 which can also be retrieved programmatically using the vSphere API (here), it unfortunately does not provide more details than simply the major/minor version (e.g. 5,5, 6.0, 6.5, etc) of the software. Recently, VMware had released a series of VMware KBs which provides a mapping between the build numbers for vCenter Server, ESXi and vSAN to their respective versions which can be found in the links below:

These are definitely a great set of resources that I know many customers including myself have been using since its release. Having said that, the process today is still pretty manual since you need to manually retrieve the build numbers for either a VC, ESXi or vSAN Host (can be automated using vSphere APIs) and then comparing that to the KBs to get the correct versions. How cool would it be if you could *easily* just point to YOUR environment and retrieve the version information for either a vCenter Server (Windows or VCSA), ESXi host(s) or vSAN host(s) without needing to manually perform this lookup each time? Well, I have just done that! I have taken all three KBs and converted that information into a simple PowerCLI script called VCESXivSANBuildVersion.ps1 leveraging our vSphere API and it provides three functions:

  • Get-VCVersion - Retrieves the vCenter Server version given a VC connection
  • Get-ESXiVersion - Retrieves the ESXi version for all hosts given a vSphere Cluster
  • Get-VSANVersion - Retrieves the vSAN version for all hosts given a vSAN Cluster

Here is an example output using the first two functions:


For the vCenter Server version output, you will notice that I am also including the OS platform of your vCenter Server, so you can distinguish between a Windows vCenter Server and a vCenter Server Appliance (VCSA) which can be useful to see if you have been #migrate2vcsa ;). For the ESXi version output, you will notice the "OriginalInstallDate" value, this is actually new API property that was introduced in vSphere 6.5 and it provides you with the original installation date of your ESXi host (more details can be found here) which is pretty neat.

Here is an example output using last function:


If you wanted to take this a step further, you could even take this output and dynamically update the vSphere UI using either Custom Attributes or vSphere Tags so you know what version the software is at any given moment. Its easy enough to set this up as a scheduled task that could run periodically so you always have the latest information provided in the vSphere UIs.

Although this is a significant improvement over the existing manual methods, I think most of you will agree that it would be ideal if this information was natively available within the product which means BOTH UI and APIs. I think we all appreciate versioning of software is not always easy and it can change from release to release for a variety of reasons, most of which may not be technical. If the vSphere platform could dynamically pull this information in either real time and/or through an offline mechanism and provide this association by default, it would greatly improve the experience when needing to troubleshoot or perform maintenance of the vSphere platform. If this is something you would like to see, please leave a comment below providing your feedback. I know I have already pinged our PMs about this and I am sure they would love to hear form you as well!

Additional Information:

Note1: Update levels can be found using the vSphere API, take a look at this article here for more details.

Note2: As of ESXi 6.5 Update 1, the Update levels are also included by default in the Embedded Host Client as shown in the screenshot below:

Note3: As of vSAN 6.2, the vSAN Management API already includes vSAN version information that can be queried. Take a look at this script here which exercises this new API. For example above, I decided to not use this new API since customers may be running older releases of vSAN which is not covered by the vSAN Mgmt API.

Note4: VMware has also published simliar build to version mapping for other VMware products which can find the complete list here.

Auditing/Logging vCenter Server authentication & authorization activities

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Recently, I have seen an increase in the number of requests from our field and customers inquiring about logging various vCenter Server authentication and authorization activities. The topics vary from identifying which log files contain which activities to to why some of this information is not available in the vCenter Server Events UI or why they are available else where. In most of these cases, customers were also looking for a way to forward these activities to their remote syslog infrastructure for auditing and tracking purposes whether that is using vRealize Log Insight (which all vSphere customers get 25 free OSI licenses!) or some other logging solution.

Having explored this topic lightly in the past and given the amount of interests, I thought I would dive a bit deeper and look at some of the common authentication and authorization workflows and provide examples of what the log entries look like and where you can find them. However, before jumping right in, I think is is worth spending a few minutes looking at the history of authentication (commonly referred to as AuthN) and authorization (commonly referred to as AuthZ) for vCenter Server and where we had started from and where we are at today to give you the full context.

UPDATE (04/08/19) - Please take a look at this blog post here for all new auditing enhancements in vSphere 6.7 Update 2 which simplifies the consumption of vCenter and vCenter SSO auditing events.

History of vCenter Server AuthN/AuthZ

Prior to vSphere 5.1, vCenter Server handled both Authentication (AuthN) and Authorization (AuthZ). As a Client, you would connect directly to vCenter Server and the AuthN service will verify who you are whether that is a local account on the OS or an Active Directory user which required vCenter Server to be joined to your AD Domain. Once you have been authenticated, the AuthZ service will then take over and verify the privileges you have been assigned to perform specific operations within vCenter Server.


In vSphere 5.1, a new service was introduced called Single Sign-On (SSO) which now takes over for AuthN services from vCenter Server. Once authenticated, it will then allow you to connect to the vCenter Server which then handles AuthZ activities


Although it may not be apparent, one major implication is where are successful and failed authentications being logged? In the past, these would reside within vCenter Server since it handled both AuthN/Authz activities, vCenter Server even included specific authentication Events that can then be seen using the UI and/or API. However, with SSO in the picture, authentication is no longer in vCenter Server but with SSO. This is why when you have a failed login using the vSphere Web Client (Flex/H5) UI it does not show up in vCenter Server and it because the logging is done but within the SSO service (which now resides in the Platform Services Controller for more recent vCenter releases).

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