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Quick Tip: Resolving OVFTool "Failed to Send File" Errors on macOS

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I frequently deploy and re-deploy VMware Virtual Appliances (OVA), which I fully automate using OVFTool from my macOS x86 system. Recently, I noticed that deployments would consistently fail roughly 3 out of 5 times with a generic error message like the following:

Deploying VCF Installer sddcm02 ...
Opening OVA source: /Volumes/Storage/Software/VCF910/PROD/COMP/SDDC_MANAGER_VCF/VCF-SDDC-Manager-Appliance-9.1.0.0.25371088.ova
The manifest does not validate
Opening VI target: vi://[email protected]/
Deploying to VI: vi://[email protected]/
Transfer Failed
Transfer Failed
Error: Failed to send file [sddcm02-2.vmdk] to the host [172.30.0.10], please check the network connection
Warning:
- The manifest is present but user flag causing to skip it
Completed with errors


While annoying 😩, I never really bothered digging into it because, after a few retries, the deployment would eventually succeed 😅

Even after upgrading to the latest OVFTool version 5.1.0 (supports VCF 9.1), the issue still continued to persist. I finally decided to enable verbose debugging during a failed deployment and reached out to OVFTool Engineering to see if they could help me understand what was happening, especially when it would eventually succeed!

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Quick Tip - How to deploy vCenter Server Appliance (VCSA) to legacy CPU without VMX Unrestricted Guest feature?

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I recently had a customer reach out who was having an issue deploying the latest vCenter Server Appliance (VCSA) 8.x to an ESXi host that had a CPU that was no longer supported. After the VCSA OVA was uploaded by the VCSA (UI/CLI) installer, it fails to power on the VM with the following error message:

The Intel "VMX Unrestricted Guest" feature is necessary to run this virtual machine on an Intel processor

This problem is only observed with older legacy CPUs that do not support some of the modern CPU instructions that is expected by most workloads today. There is workaround for those that still wish to run on unsupported hardware, which may yield other unexpected behaviors, by adding a VM Advanced Setting monitor.allowLegacyCPU = TRUE

However, there is a chicken/egg problem that user was not able to add this setting before the VM was automatically powered on by the VCSA Installer.

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Create Windows 11 Virtual Appliance using Tiny 11 with only 2GB memory

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I recently came to learn about a really cool project called Tiny 11 which is a stripped down version of Windows 11 Pro 22H2 that can run with just 2GB of memory and 8GB of storage. While you would probably not use this for production workloads, it could be interesting for those with homelabs and can even for demo purposes.

Disclaimer: Tiny 11 is not an official project from Microsoft, use at your own risk. If you are interested in creating an optimized Windows 10 or 11 image, you can also check out these VMware resources here and here to produce a similiar size image using official Microsoft tools and images.

UPDATE (02/16/23) - There is now an Arm version for Tiny 11, which is great for anyone using the ESXi-Arm Fling and the technique in this blog post would also apply.

After performing a manual installation of Tiny 11, I thought it would be neat if I could build a Virtual Appliance (OVA) for Tiny 11 and also add custom OVF properties, which would allow anyone to customize the OS further without having to rely on any external tooling.

In fact, I had demonstrated this concept back in 2019 using Windows Server 2016 in this blog post and I figure it should be easy enough to also do the same for Tiny 11 or even standard Windows 11! With a bit of trial/error, I was indeed able to create a simple Tiny 11 OVA that includes the following OVF properties as shown in the screenshot below.


My initial goal was to fully automate the building of a Tiny 11 OVA with custom OVF properties using Packer. However, after many attempts, I was not able to figure out the correct autoattended.xml configuration and decided on a semi-manual approach which is detailed in the instructions below. If anyone is able to figure out how to get Tiny 11 installed via Packer, then I may revisit this topic and automate the remainder of the setup.

Note: The instructions below are not specific to Tiny 11 in any way and is also applicable to standard Windows 10 or 11 image.

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