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We are currently on Jira server and thinking of moving to Jira Cloud. I have valid licence till March 2021. However, there are a few concerns that prevent me from hitting the start cloud trial button in my.attlassian.com
Thanks for writing in about Extended cloud trials for server and Data Center customers .
To answer your questions:
These trials are designed for customers just like you, who are currently on server but need time to explore cloud or plan a migration.
It sounds like you're early in your thinking about moving to cloud, so if you haven't seen them already, a few more good resources to look at are:
Please don't hesitate to reach out with further questions.