In this episode of The Windows Podcast, Lucas and Luna explore how Microsoft is quietly restructuring enterprise software sales around the concept of 'Microsoft 365 Copilot' and 'Microsoft 365 Frontline' tiers. They drill into a specific change: the introduction of per-user, per-month pricing for AI features that are gated behind higher subscription tiers, and what this means for IT procurement teams. Using a case study of a fictional 5,000-employee manufacturer, they calculate the difference between a 'basic' enterprise seat and a 'Copilot' seat — roughly $30 per user per month versus $60. Lucas argues this is a deliberate strategy to increase average revenue per user without raising list prices, while Luna pushes back on whether the AI features are worth the premium. The conversation touches on the PlayStation vs Nintendo analogy, the bundling playbook from cable TV, and a surprising stat: historically, enterprise software price increases of over 20% have led to a 5-7% churn rate. They also discuss whether IT managers should unbundle or renegotiate. The episode ends with a low-key donation ask and a final thought on negotiation leverage.