About ten years ago my sister-in-law broke the screen on her mobile phone. She'd had an older iPhone and when she went to upgrade, none of the upgrade processes worked because her OS was so far behind that they couldn't transfer her information smoothly. She had been avoiding OS updates because they interrupted her life, but that was now a problem because the world had marched so far beyond her version that there weren't tools, or at least, no one was interested in trying to perform an upgrade across multiple OS versions (I think it was 3 or 5 versions). I ran into this recently with someone else I knew, but not for a mobile phone. For TFS 2015. This customer had been working along with this older system and is finally ready to upgrade to Azure DevOps in the cloud. They wanted to know if they could somehow upgrade the TFS database and move all that data easily into the cloud. I said this wasn't likely easy as this isn't an upgrade, but an export and import of a lot of data. Microsoft offered a path, but it was multiple upgrades before an export/import, which was deemed too expensive. Right now, I'm not sure what they're doing to do. Read the rest of The Dangers of Not Upgrading