pfSense keep crashing during boot up after upgrading from 2.6 to 2.7.

[piotres]

The only "fix" for now is booting from kernel.old but a lot of errors.

It is 2.6 CE Edition of pfSense setup on vmWare ESXi-6.0.0-20160302001-standard

During upgrading CE from 2.6.0 to 2.7.0 pfSense crashes during reboot. The only "fix" for now is running it from kernel.old but routing and interfaces are the mess. Interesing fact - appliance seems to be working. IPsec tunnels are up, I can VPN to it, traffis going through. WHen looking in Interfaces in GUI no traffic at all.
Also constantly notification on CLI: linker_load_file: /boot/kernel.old/if_vmx.ko - unsupported file type
interface vmx2 already present in the KLD 'kernel'

I tried:
certctl rehash returns bunch of "Skipping untrusted certificate" messages

pkg-static update -f

Newer FreeBSD version for package zabbix6-agent:
To ignore this error set IGNORE_OSVERSION=yes

package: 1400094

running kernel: 1400085 Ignore the mismatch and continue? [y/N]: y Processing entries: 100% pfSense repository update completed. 550 packages processed. All repositories are up to date.

pkg-static install -fy pkg pfSense-repo pfSense-upgrade

[1/1] Upgrading pkg from 1.19.1_2 to 1.20.8_3...
sysctl: unknown oid 'user.localbase'
Skipping bunch of untrusted certificates

Installed packages to be UPGRADED:
pfSense-repo: 2.7.0_2 -> 2.7.2 [pfSense]
pfSense-upgrade: 1.0_33 -> 1.2.1 [pfSense]
Installed packages to be REINSTALLED:
pkg-1.20.8_3 [pfSense]
Number of packages to be upgraded: 2
Number of packages to be reinstalled: 1
sysctl: unknown oid 'user.localbase'

[3/3] Upgrading pfSense-upgrade from 1.0_33 to 1.2.1...
[3/3] Extracting pfSense-upgrade-1.2.1: 100%
You may need to manually remove /usr/local/etc/pkg.conf if it is no longer needed.

And then when I ran
pkg autoremove
I get ld-elf.so.1: Shared object "libssl.so.30" not found, required by "pkg"

pfSense support suggested reinstalling pfSense by deleting and re-installing hard drive on VM. I tried last night, deleted hard drive in the VM configuration. Added new one and power on vm. Installation started and crashes in almost exact way when updating from 2.6 to 2.7. !
Seems like the only way will be deleting VM itself and create new one from the scratch but I am curious what could cause such issue?

Short screen capture movie during installation process. Link

[stephenw10]

What VM version is that? If it's an old VM it might not support FreeBSD 14 which 2.7 is built on.

Or an old ESXi version could also present like that. Must be 8.x.

[piotres]

@stephenw10
This one is setup as Linux on CentOS 4/5/6/7 (64-bit). It was installed like that and worked well for years.
When update to 2.7 and then reinstall failed I tried to create a new VM on CentOS and install pfSense. It installed without issues.

[stephenw10]

Right. The FreeBSD base changed from 12 to 14 between pfSense 2.6 and 2.7. Older versions of both ESXi and the VM version within it do not support FreeBSD 14 so be sure both are new enough.