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I'm trying to simply install some trial apps and failing. For example User Switcher for Jira. It tries to automatically generate trial license and fails. So, can't even try these apps using Free Trial. What's the issue?
Is there a better (built-in/free) way to switch to (impersonate) a user to try if his roles are configured correctly?
You can not create licences for Atlassian systems that are going away.
Have a look at what you are trying to create, my guess is that you can not.
Apps for Server and Cloud are totally different pieces of software. There's often no point in testing an app on server if you're going to move to cloud soon. You should be testing the app on Cloud.
Not if you need the app to migrate to cloud, bad move. I need to move app a to app b but I cant get a trial for app b because of this.
If you need the app look Atlassian Marketplace for it.
Select data center and upload the jar to your server.
You will get a banner saying the app was meant for data center this can be a non-issue and might be safe to ignore depending on the app.