Windows Server Upgrade

I’m planning on doing a few in-place Windows Server upgrades from 2012 to 2016. I can create a test environment and give it a try, but I was wondering if anyone has had any experience in doing this and could give me any pointers on anything that needs to be done with IIS or Lucee beforehand or what could break in doing this. Thank you!


if its a VM,create a snapshot / checkpoint
if its not, do what ever backups you feel makes you need
Perform windows update to the very latest patches provided by Microsoft
Perform any vendor firmware patches provided by your hardware vendor
Make note of any custom registry settings, ODBC connectors, or any custom local policies the server has
Disable UAC / DEP
truncate all your logs
if you are running any kind of database on the same server, gracefully shut it down and leave it off, disabling the service(s) for it until you have upgraded
additionally, perform a full backup of the database and move the file off the server
delete all your temp files
disable all your scheduled tasks
disable any unnecessary startup items
disable any third party antivirus
run defrag
run sfc /scannow
restart the server (optional but highly recommended)
insert your media
perform install
re-enable services
re-create odbc connections
re-start services
check for connectivity
re-enable DEP
re-enable UAC
complete patches /updates

We did an upgrade (new install) from 2012 to Windows 2019. Taking a raw look at Lucee and IIS at OS level, there isn’t much difference between 2012 and 2019, just that there are some more features… e.g. for IIS http2 and better TLS support. But of course, all depends on your requirements. Consider using tools like CommandBox cfconfig to export/import/transfer Lucee settings.

One thing is it won’t update Java and Tomcat. You would need to make sure that is updated to latest security updates.