Four things to do before upgrading to Azure DevOps Server 2019
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IT implementations can be wildly successful or crash and burn, depending on how well you plan. Before upgrading to the new Azure DevOps Server 2019, make sure to do the following:
Check your current software. If you’re running anything earlier than Team Foundation Server 2010, you’ll need to do some extra work before upgrading. Otherwise, the update should be relatively smooth.
Update your UI documentation.One of the major changes in Azure DevOps Server 2019 is the user interface, which has changed significantly. It’s been modernized to have a smoother look and clearer navigation, including a variety of new hubs like Work Items, Boards, and Queries. To avoid any unnecessary downtime, be sure to read up a bit on how things have changed and update your internal educational reference material before deploying.
Plan for what's being deprecated.Elements like the client object model and SOAP API’s are still supported in this version, but when the next updates are released, they’ll be deprecated. Make sure you have a plan for your workflow to accommodate replacements.
Review security patches. Since its release in March of this year, the DevOps Server has had nine bug fixes, and there are sure to be more.