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DLP Upgrade Strategy

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I need a solution

Hello everybody

I am currently working out an upgrade strategy for a DLP environment.
Current version running is 11.6.3 and target version is 14.6.
There is one physical W2k8R2 server hosting the Enforce and Endpoint Prevent roles.
The DB is on a central Oracle Cluster, running on 11.2.0.4 and currently having around 7.8 million incidents.

So far, nothing special, no big deal.

What I am concerned is that from 11.6.3 there are a lot of versions to be upgraded until I'll end up with 14.6. Therefore, a lot can and probably will go wrong.

Biggest concern is the fact that it is pretty costly to snapshot and revert a physical server. So if it's blowing up, I am pretty much on a bad side with the current setup.
To mitigate this, first I want to create a VM from the physical server. This will give me the possibility to take snapshots and revert in the very likely case of trouble.

Is there anyone who did something similar already?
Even if everything is working fine, DLP 14.6 will in the end run on W2k8R2. Will DLP 14.6 be running on W2k8R2 at all?

What my preferred approach would be is setting up a new 14.6 environment and then attach the DLP DB to the new environment.
Is there _any_ possible way to achieve something like this?

As you can see, there are a lot of questions but not many solutions at the moment. I am thankful for each input which is lighting up the dark.

Cheers

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