KB : How to extend TFS4JIRA Cloud add-on evaluation license?
According to the Atlassian Customer Advocates team they are NOT able to extend the evaluation license for Cloud customers that are paying on a monthly basis. The system doesn't allow to extend the evaluation further. However, if the request is within the evaluation time and the Cloud customer is running in an annual subscription, it is possible to extend it. Please double check this information with Atlassian when asking for an extension.