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We currently run Jira and Confluence on prem, Service Desk 4.1.0 and Jira Software 8.1.0. We'd like to learn how to get a support contract and update to a more recent version but support/sales only tell me to post to the community forum. Has anyone had experience performing upgrades who could walk me through the process or how to pay for support again? Thanks in advance.
Welcome to the community.
You can look into the premier support package from Atlassian here: https://confluence.atlassian.com/support/premier-support-offering-details-593035672.html
They provide guidance and support for upgrades if you don't have the experience. If you don't get it the will tell you to come here and hopefully someone will help you for free.
The other option is to contact atlassian partners in your region that would assist you too.
A partner would also be able to help you get your licence renewed during an upgrade/advice engagement.