By November 30, 2025, there is some evidence consistent with parts of Saks’s thesis, but not enough – and the time horizon is too long – to say the full conditional prediction has clearly come true or failed.

1. Regulators did move toward a la carte-style remedies, at least for Teams
After the Slack/Salesforce complaint, the European Commission formally found that bundling Teams with Office/Microsoft 365 gave Teams an unfair distribution advantage and accepted legally binding commitments from Microsoft. Microsoft must now offer Office 365 / Microsoft 365 suites with and without Teams worldwide, with mandated price gaps between the two options and minimum standalone pricing for Teams, enforced for seven years. (microsoft.com)
Separately, the Australian ACCC has sued Microsoft over how it presented a more expensive Microsoft 365 + Copilot plan versus a cheaper “Classic” option without Copilot, again pushing toward clearer, a la carte‑style choices. (windowscentral.com)
These moves do not perfectly implement Saks’s exact remedy (he wanted the summed a la carte prices to equal the bundle price), but they undercut the simple "Teams is free in the bundle" story he was reacting to. That makes the antecedent of his conditional ("if we don’t do that") only partially true.

2. Microsoft is continuing to add and bundle new capabilities into Microsoft 365
Since mid‑2024, Microsoft has indeed layered more products and functionality into its 365 ecosystem:

• In October 2025 it launched Microsoft 365 Premium for consumers, a higher-priced subscription that deeply integrates Copilot AI across Word, Excel, Outlook and more, plus Defender security features and 1 TB storage – effectively a new, richer bundle tier. (reuters.com)
• Internal planning documents and announcements describe new AI services like “Tenant Copilot” and broader “Agent Factory” concepts being built directly into Microsoft 365, showing a continued pattern of embedding new functionality into the suite. (businessinsider.com)
  This supports the narrower part of his claim that Microsoft would keep adding new products/features into the 365 bundle on an ongoing basis.

3. "Systematically dominate broad swaths of enterprise software" is a long‑run, structural claim
As of 2025, Microsoft already had very high share in enterprise productivity (over 80% in the enterprise segment of office productivity software) and substantial positions in cloud and security, but it still faces strong, viable competitors across major enterprise categories (AWS and Google Cloud in IaaS, Salesforce/Oracle/SAP/others in enterprise apps, Google Workspace in productivity, and a large ecosystem of security vendors). (markets.financialcontent.com)
Regulatory pressure is increasing, not disappearing: the EU DMA gatekeeper regime, the EU Teams commitments, and UK/CMA scrutiny of Microsoft’s cloud licensing all push against unchecked expansion via bundling. (markets.financialcontent.com)
Given that Saks framed the outcome as something that would occur "over time" if regulators failed to act, and we are only ~17 months past the June 29, 2024 episode – with major regulatory interventions still unfolding – it’s too early to say whether Microsoft will, because of bundling, end up "systematically" dominating many more enterprise software segments than it already did.

4. Net assessment

• Partially borne out: Microsoft has continued to enrich and promote bundled 365 offerings (including new AI and security capabilities), consistent with his concern about the power of the bundle. (reuters.com)
• Partially undercut: Key regulators have imposed a la carte and pricing-structure remedies around Teams and are scrutinizing other aspects of Microsoft’s cloud and licensing behavior, so the simple “no regulatory response” scenario he described has not materialized. (microsoft.com)
• Too early on the core outcome: Whether this will ultimately let Microsoft "systematically dominate" broad new swaths of enterprise software is a multi‑year question, and current data does not yet show a clear, new wave of monopoly-style dominance caused by post‑2024 bundling.

Because the central, long‑term consequence Saks predicted (systematic domination across broad enterprise categories due to unchecked bundling) cannot yet be clearly confirmed or falsified, the prediction is best classified as inconclusive (too early) at this point.