Field notes from the migrations.

Deadline: Jul–Nov 2026 stack

IT layoffs vs. 2026 deadlines: who runs the work?

H1-2026 tech cuts collided with a stacked Microsoft EOL calendar. When a team shrinks, the SharePoint, Exchange, and CMMC deadlines don't move — how a senior bench fills the gap without touching headcount.

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Deadline: ESU ends Oct 2026

Exchange Server SE: what modern servicing commits you to

You're on Exchange Server SE — now what? Single-version modern servicing, mandatory CU currency, the cloud dependency for on-prem servers, Server Core, and the coming product-key requirement.

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Deadline: SE CU2, H2 2026

Exchange SE CU2: the coexistence deadline after EOL

Exchange 2016/2019 are out of support; the paid ESU bridge ends Oct 2026. 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: ESU Period 2 ends Oct 2026

Exchange ESU Period 1 expired — your real deadline

The paid Exchange ESU bridge is nearly spent: Period 1 expired April 14, 2026 and Period 2 ends October 2026 (final). 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 2016 & 2019 EOL July 14, 2026: three paths

SharePoint 2016 and 2019 both end support July 14, 2026 — no ESU at any price. SPO migration, Subscription Edition, or selective hybrid, with cutover math for 50/200/500 users.

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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; the paid ESU bridge ends Oct 2026. 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.

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