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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 - Encoding special characters for OVFTool on the command-line

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If you use strong and complex passwords that contain special characters (which you should), it can some times be challenging from an automation perspective on how to properly escape these characters, which can also depend on the scripting or programming language that you are using.

Today I learned about a nice little enhancement in OVFTool 4.4 or later, which makes it easy to handle complex passwords containing special characters by supporting URL encoding for these characters. This is also great for those writing automation scripts and not having to input the password interactively but can now be added to OVFTool command-line string.

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Quick Tip - How to deploy OVF/OVA to multiple networks using OVFTool?

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For automation purposes, customers use the handy OVFTool, which is a multi-platform command-line utility for uploading or exporting OVF/OVA images. During an upload, users would typically specify the --network argument which will assign the desired vSphere Network to the deployed VM and if the VM included multiple network adapters, it would assign the same network which can then be modified during post-deployment.

What if you had a OVF/OVA that included multiple network adapters and you wanted a different network for each adapter? Luckily, this is also supported with OVFTool by using the --nic argument, which expects the network name as codified within the OVF/OVA to tell OVFTool which vSphere Network to assign. You can find OVF/OVA network name by simply running OVFTool command against the OVF/OVA without any arguments and you should see the name as shown in the screenshot below.


Note: The network name in the OVF/OVA MUST be unique to be able to assign different networks during upload.

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