Writing

Field notes from the migrations.

Cornerstone writing on the EOL waves, the platform shifts, and the identity work happening right now in the Microsoft project space.

Deadline: SE CU2, H2 2026

Exchange Server SE: the CU2 coexistence deadline

Exchange 2016/2019 are out of support and there's no ESU for Exchange. SE CU2 will block coexistence with legacy Exchange — closing the last clean migration window. The senior operator's runbook.

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Deadline: Nov 10, 2026 (CMMC Phase 2)

Copilot governance one year on: the 12,000-permission reckoning

One year after the oversharing warning, mid-market Copilot tenants are leaking HR, finance, and legal docs. The 90-day playbook using Purview DSPM, SharePoint Advanced Management, and Restricted SharePoint Search.

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Deadline: End of Q2 2026

Kerberos RC4 April 2026 enforcement: mid-market triage runbook

Microsoft's April 14 patch flipped DCs to AES-SHA1-only and broke RC4 service-account logins. The 3-hour triage runbook and the Q2 cliff that removes rollback.

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Deadline: EOL Oct 14, 2025

Exchange 'ESU expired'? There's no Exchange ESU — here's the real deadline

There is no ESU program for Exchange Server. What actually expired was support, on Oct 14, 2025. The real deadline, four exit paths, and hour ranges for 50–1,500 seats.

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AD functional level on Windows Server 2019/2022: not stuck at 2016

Microsoft skipped Server 2019 and 2022 functional levels. Server 2016 IS the maximum for any 2019/2022 forest. What Server 2025 (behavior version 10) actually adds.

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Deadline: Identity-substrate

AD Tier-0 in 90 days: the mid-market edition

Microsoft's enterprise Tier-0 guidance is overkill for 100–500-user shops. The four controls and 12-week plan that close 80% of the gap at under 25% of the cost.

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Deadline: M&A integration

Field Notes: M&A 2-tenant merge in 60 days

Anonymized field notes — $8B parent acquires 200-employee subsidiary. Two M365 tenants, one identity model, 60 days. Power Platform, shared apps, Teams chat, OneDrive personal data.

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Deadline: Nov 10, 2026

CMMC L2 pre-assessment: what $15K buys you

A fixed-fee $15K pre-assessment for a 100–300-user GovCon shop — SSP draft, POA&M draft, GCC High eligibility, NIST 800-171 gap register, third-party app compatibility, two weeks.

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Deadline: Renewal-driven

VMware to Azure vs Hyper-V: 500-VM decision guide

Six dimensions that decide whether a 500-VM mid-market VMware exit lands in Azure IaaS or Hyper-V on-prem. Two anonymized walk-throughs and a decision matrix.

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Deadline: Jul 14, 2026

SharePoint Server 2019 EOL July 2026: three paths

No ESU program for SharePoint. SPO migration, Subscription Edition, or selective hybrid — with cutover math for 50/200/500-user environments.

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Deadline: Pre-rollout

Is Microsoft Copilot HIPAA compliant? Read the BAA

Microsoft's BAA covers the platform, not your tenant configuration. The four pre-deployment fixes that keep Copilot on the right side of HIPAA.

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Deadline: Renewal-driven

After Broadcom: 250-VM Hyper-V migration in 90 days

Anonymized field notes — $310K Broadcom renewal turned into a $35K Hyper-V migration with a four-month payback.

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Deadline: SE CU2, H2 2026

Exchange Server 2019 EOL: your real migration deadline

Exchange 2016/2019 lost support Oct 14, 2025 — and there's no ESU for Exchange. The four migration paths and the deadline that actually bites: SE CU2.

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Deadline: Renewal-driven

VMware after Broadcom: your real exit options

vSphere → Hyper-V vs Nutanix vs Scale Computing vs Azure Stack HCI vs Proxmox. When each lands.

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Deadline: Pre-rollout

Copilot readiness: the 12,000-permission problem

Why oversharing becomes a data-loss event when Copilot turns on, and how to fix it before you flip the switch.

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Deadline: Nov 10, 2026

GCC High before CMMC Phase 2

What defense contractors need before Nov 10, 2026, realistic timelines, common mistakes.

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Tenant-to-tenant M365 migration: a playbook

The M&A and divestiture story, what tools fit when, and how to budget realistically.