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!
It turns out the issue is caused by macOS using LibreSSL by default. The TLS 1.3 implementation in LibreSSL 3.3.6 differs significantly from OpenSSL, resulting in the intermittent deployment failures that I had been seeing 🤬
The suggestion from engineering was to force the TLS version to 1.2 by appending the following:
--sslVersion=TLSv1_2
After making the change, the issue was immediately resolved and my deployments now have a 100% success rate on the first attempt! Sometimes it does not pay to be lazy and actually investigating an issue 😂
Thanks for the comment!