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!

