this post was submitted on 13 Jan 2025
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Your #4 is the same as my #3. Play out your #4 and it ends up as my #3:
Security or Compliance teams raise the concern with continuing to run the EOL OS, they demand the App team power down the offending servers or upgrade. App team escalates to leadership advocating for the upgrade and they ask for the funding. Leadership asks for a business case justifying the large spend requiring the ROI numbers. App team mostly shrugs because the ROI are intangibles of security or support-ability. Leadership sees no immediate monetary benefit being realized in the next 2 quarters from a costly upgrade and instead chooses to accept the risk. They send an exception order to Security or Compliance teams that this EOL OS should continue running as is and the App team shouldn't be bothered anymore.
...and we end up with my #3.