How much time does it take to manually test an upgrade? How much time does it take to manually execute recurring maintenance tasks? How many times per year do you perform these tests? Use this worksheet to start a test plan.
Also see: Jira Upgrade Automated Test Cases
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It saves time to automate tests that don't absolutely require a human to perform manually. There are plenty of free and paid applications to automate web application tests. Start by asking your QA team what they use for their automation needs. They may even be able to help you get set up with sample test cases.
List the standard regression and scheduled maintenance tasks suitable for automation. Here's a sample test plan to get you started.