On Wed, 2016-01-27 at 00:04 -0500, Ugo Bellavance wrote:
> Hi,
> 
> We're in the process of planning the upgrade of our main site's
> pfSense 
> firewall. It is currently running 2.0.1-RELEASE and we want it to be
> at 
> the latest version.  It is running in a VMWare VM (amd64).

As it is a VM you can try before you buy!  Clone the VM.  Create some
new vSwitches but don't attach them to physical NICs.  Create yourself
a virtual workstation for a client if you like.  You could also deploy
one or more "little" pfSenses to emulate the internet and even put
client machines behind them.  I use the System Rescue CD to create
multiple workstations with minimum effort that have a GUI, browser and
lots of tools available.

Now do the upgrade and test the functionality.  If you really are
worried about anything spend plenty of time on this.

When your maintenance window arrives, dump a copy of the config, have a
copy of the install .iso available, snapshot the VM first, update it
and off you go.  Back out the snapshot after a few days, don't leave it
there.

I and many others here have lots of VMware VM pfSense machines.  My
main work one started life on vSphere 4 as pfSense 1.2.something and is
now bang up to date.

Cheers
Jon
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