Upgrading from SM V14 to the latest and greatest. Looking for feedback and "gotchas"
Question asked by Curtis Kropar www.HawaiianHope.org - 12/27/2023 at 9:59 PM
So, In about 2 weeks or so, we will be finally upgrading from SM V14 to the latest and greatest. 
Our old servers did not have the capacity to manage the upgrade (speed, ram and storage space) and this weekend we are doing a major upgrade to significantly better hardware and VM capability.

So, I am looking for feedback and any "gotchas" from all of you peeps of anything we really need to watch out for, "gotchas", the "oh by the way's" and anything that you might have done differently had you to do it again.
We are moving from a 2008 SR2 to a 2022 server (as VM's),That is also a web server hosting about 20 domains and uses PLESK as the management tool.  Our current setup uses a 2 drive layout, C drive for the OS and programs, Drive D holds all of the domains and email.  
Keep that layout or move everything to a single Drive since it is a VM ?
Would you "upgrade" the windows or do a fresh 2022 install and Migrating (or recreate) domain data ?
Fresh install SmarterMail and migrate data or upgrade overlay ?

Any other tips, tricks, suggestions ?

www.HawaiianHope.org - Providing technology services to non profit organizations, low income families, homeless shelters, clean and sober houses and prisoner reentry programs. Since 2015, We have refurbished over 11,000 Computers !

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JerseyConnect Team Replied
Keep all the domains and mail on a separate volume. This make future OS upgrades easy as you can just build a VM with the new OS, attach the mail volume disk to it and then install SmarterMail. No need to copy all that mail data between systems. Having multiple volumes on a VM should also improve your backup and restore times, since your backup software should be able to read/write to multiple VM disks at the same time. Just for the improved RTO, we actually split our mail data across 2 volumes, one for production mail and another just for all the mail archives.

In your case it sounds like you're going from a physical server to a VM and the current server can't handle the upgrade. So then you'll need to robocopy the mail data to the new server. Then if I were in your position I'd do a test migration. Take a snapshot of the VM, install v14 on that server and check for issues before doing the SM upgrade. Then check for issues again before doing the process for real.

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