TagVMware Fusion

Virtual Machine Fails To Boot After Uploading to vSphere From VMware Fusion

As I wrote in my recent Projects for 2018 blog post, one of the things I wanted to do this year was to setup a VMware ESXi host once again. I have been using VMware Fusion and Workstation so much in the last few months that it would only make sense to also have a server to upload and download VMs to and from. So I did configure the host and I immediately started uploading all the VMs I had on my desktop machines.

All of them uploaded successfully, but one behaved strangely: in VMware Fusion, I would right-click on it, select Upload to Server…, choose my ESXi host and datastore and then select Upload, but the upload process completed immediately, in something like one second. This was very weird because this VM was 15 GBs in size so that was no way the upload had completed already.

However, what was even stranger was that the ESXi host showed the machine correctly uploaded to the host datastore, with configuration files and virtual hard drives. However, attempting to boot the VM would result in a network boot taking place, quickly followed by an Operating System not found error right afterwards, so the virtual machine would consistently fail to boot. This made me realize that there was definitely an issue with my virtual hard disk.

Operating System not found error after network boot

This is the Operating System not found error that would come up after uploading a virtual machine from VMware Fusion to a vSphere host

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How To Export A Virtual Machine From VirtualBox And Import It Into VMware Fusion Or Workstation

You would think that exporting a virtual machine from VirtualBox and importing it into VMware Fusion or VMware Workstation was a straightforward process right? Especially because you can use the ubiquitous OVF format, also right?

Well, not really, unfortunately. If you try to import a VM into either Fusion or Workstation after exporting it with VirtualBox, it is very likely you are going to receive an error message. Simply exporting and importing will not always work (in my experience, an exception to this is when you export from VirtualBox on Windows and import in VMware Workstation). You will either get errors about size mismatches or corrupted OVF files or something else entirely.

The official VMware documentation was not helpful at all. Even if you tried following the multiple articles on this topic, you would still keep receiving the same error messages. For reference, these were the articles I followed:

Judging by the ratings of these articles, I suspect I am not the only one who found them unhelpful ;)

Luckily, it is indeed possible to do this, but the process involves some manual work. This is what you should do if you want to export a VM from VirtualBox and import in into VMware Fusion or Workstation.

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