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Federal Modernization Workbook

For the CIO: The Clocks and the Cost

A one-page brief for the meeting that approves the pre-flight

A one-page brief for the CIO: the external dates that land on one estate, why one program can sequence them when separate projects can only race them, and what the first step costs. Word download included.

One of four reader briefs that expand the pitches in Making the Case at Your Agency. Hand it over before the meeting, with The One-Page Ask.

Download	Use
Brief_for_the_CIO.docx	The brief below, one page, with your number to fill in

Design guidance

The pitch and the framing are this workbook’s design guidance. The facts come from the chapters under Go deeper, where each is footnoted to its primary source. Dates change, so check them before you use this.

The brief

The point: the dates are set outside the agency and they all land on the same estate. One program can sequence them. Separate projects can only race them.

The clocks

Clock	Date	What it asks
OMB M-26-14 Agency Logging Plan	November 18, 2026 (calculated)	Then maturity Levels 1, 2 and 3 by December 18, 2026, February 16, 2027 and July 6, 2027 (calculated; confirm with the CISO’s office)
Windows Server 2016 end of support	January 12, 2027	The workbook plans on these being gone; any that remains is an exception
CISA BOD 26-02	February 5, 2027	Decommission listed end-of-support edge devices
Windows Server 2019 end of support	January 9, 2029	The next upgrade, on a date already set

Running past end of support becomes a risk acceptance an authorizing official has to sign.

The cost

The first step is a four-week pre-flight with no vendor decision. It produces an inventory, an owner and a date.
The program has no license of its own, but the services it uses do: Microsoft Entra ID P1 for Conditional Access, and P2 or Entra ID Governance for Privileged Identity Management.
Budget lines that treat the work as independent will produce independent answers to shared questions. Fund and govern it as one sequence.

What we ask of you

Own scope, funding and sequence with the executive sponsor.
Support the four-week pre-flight, with a named sponsor, a named steward and a date.
Keep Gate G5, the retirement of Active Directory, as a decision you make with the sponsor.

Our number

Windows Server 2019 servers, with no 2016 server left: [count]

Go deeper

Topic	Chapter
The clocks, and how the M-26-14 dates were calculated	Book 00, Chapter 01
Why one program, not a set of projects	Book 00, Chapter 01
What the program is and isn’t, and its licensing	Book 01, Chapter 09
Gates and where to start	Book 01, Chapter 12

Continue

For the CISO → · The One-Page Ask · Start Here

Version and revision history

Version 2.0, in edition 2026.11.5 (November 8, 2026). Every edition is kept on the Archive page; every change between editions is in the commit history.

Versions of this guide, newest first
Version	Edition	Date	Changes
2.0	2026.11.5	2026-11-08	Release 2.0, the baseline: checked against every other book; Draft becomes Baseline; Meeting pack: The One-Page Ask, Charter Sign-Off Sheet and four reader briefs (#390); Approve 116 gated pages (Nov 7); fix RMF map stale-review test (#457); Release 2.0: Draft becomes Baseline (#491)