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

06.13.2026 by William Lam // Leave a Comment

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!

[Read more...]

Categories // OVFTool Tags // ovftool

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

03.02.2023 by William Lam // 1 Comment

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.

[Read more...]

Categories // OVFTool, vSphere 8.0 Tags // ovftool, vcenter server appliance, vSphere 8.0

Quick Tip - Easily move or copy VMs between two Free ESXi hosts?

01.30.2023 by William Lam // 10 Comments

There are many options when it comes to moving or copying Virtual Machine(s) across two ESXi hosts that are fully licensed and can be managed by a vCenter Server, but what about standalone ESXi hosts that only use the Free ESXi Hypervisor license?

Luckily, we have a couple of native solutions from VMware that not only work, but they are completely free to use, which some folks may not even realize!

[Read more...]

Categories // ESXi, vSphere 7.0, vSphere 8.0 Tags // free esxi, ovftool, vCenter Converter

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William is Distinguished Platform Engineering Architect in the VMware Cloud Foundation (VCF) Division at Broadcom. His primary focus is helping customers and partners build, run and operate a modern Private Cloud using the VMware Cloud Foundation (VCF) platform.

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