I am working with Jira server on our intranet that has no marketplace access due to the security of our intranet. We have a few paid add-ons that will need to be updated since we are moving from Jira 7 to 8. Will the licenses be able to be transferred if I copy them all down, disable add-ons then update and upload the new versions? Will any data be lost in doing so?
Yes, you can transfer everything in exactly the way you have described.
The licence keys are all you need to re-licence the apps in the new server, and those are available in your my.atlassian account as well.
You will lose no data, but the apps will upgrade the data when you go through the upgrade process.
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