Why Windows Enterprise Upgrades Keep Getting Pushed Back episode artwork

EPISODE · May 31, 2026 · 7 MIN

Why Windows Enterprise Upgrades Keep Getting Pushed Back

from The Windows Podcast with Fexingo: Microsoft, PC, and Enterprise Windows Conversations · host Fexingo

A deep dive into the data behind the slow Windows 11 enterprise adoption rate — currently around 35 percent in large organisations. Lucas and Luna examine the real reasons IT departments are delaying upgrades, from app compatibility risks and driver certification bottlenecks to the hidden costs of re-imaging fleets. They zero in on a specific case: a mid-sized manufacturer that spent $1.2 million testing legacy line-of-business apps only to find that 8 percent still break under Windows 11 24H2. The episode also touches on Microsoft's shifting support timelines and what the October 2025 Windows 10 end-of-life deadline means for budgeting cycles. Practical takeaways for IT decision-makers weighing the cost of staying vs. migrating. #WindowsEnterprise #Windows11 #ITManagement #EnterpriseIT #AppCompatibility #Microsoft #Windows10 #EndOfLife #ITStrategy #EnterpriseUpgrades #DriverCertification #LobApps #PatchManagement #Tech #BusinessPodcast #FexingoBusiness #TheWindowsPodcast #EnterpriseTech Keep every episode free: buymeacoffee.com/fexingo

A deep dive into the data behind the slow Windows 11 enterprise adoption rate — currently around 35 percent in large organisations. Lucas and Luna examine the real reasons IT departments are delaying upgrades, from app compatibility risks and driver certification bottlenecks to the hidden costs of re-imaging fleets. They zero in on a specific case: a mid-sized manufacturer that spent $1.2 million testing legacy line-of-business apps only to find that 8 percent still break under Windows 11 24H2. The episode also touches on Microsoft's shifting support timelines and what the October 2025 Windows 10 end-of-life deadline means for budgeting cycles. Practical takeaways for IT decision-makers weighing the cost of staying vs. migrating. #WindowsEnterprise #Windows11 #ITManagement #EnterpriseIT #AppCompatibility #Microsoft #Windows10 #EndOfLife #ITStrategy #EnterpriseUpgrades #DriverCertification #LobApps #PatchManagement #Tech #BusinessPodcast #FexingoBusiness #TheWindowsPodcast #EnterpriseTech Keep every episode free: buymeacoffee.com/fexingo

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Why Windows Enterprise Upgrades Keep Getting Pushed Back

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How long is this episode of The Windows Podcast with Fexingo: Microsoft, PC, and Enterprise Windows Conversations?

This episode is 7 minutes long.

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This episode was published on May 31, 2026.

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A deep dive into the data behind the slow Windows 11 enterprise adoption rate — currently around 35 percent in large organisations. Lucas and Luna examine the real reasons IT departments are delaying upgrades, from app compatibility risks and driver...

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