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I've been tasked with migrating a physical OpenBSD 4.0 boxes to our VMWare ESXi farm. I used VMWare's Converter 4.1 CD to perform a cold migration which completed successfully. Prior to the first boot of the VM the network adapter was adjusted to E1000, SCSI controller to LSI Logic Parallel and the guest operating system to FreeBSD (32-bit). The first boot up resulted in a "Loading PBR for descriptor 4...done. Bad PBR signature" error. I then booted a 4.9 installation CD to shell, ran fdisk -u sd0 which allowed the box to start to boot but it panicked with a "cannot open disk, 0x400/0xd00, error 6."

If I boot from the 4.9 installation CD and perform an upgrade the VM successfully boots but Apache is angry because of size mismatches on some libraries.

I feel like I'm trying to do the impossible or am going about it the wrong way. Hoping someone can speak from experience to spin me in the right direction or tell me to give up and migrate the applications to a newer and virtual OS.

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Just do a fresh install with 5.0 (it is the latest available version). Then later move the configuration files, user data to the new virtual machine.

Upgrade between next releases are supported. However you cannot skip that many versions and expect it to work.

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