Many companies have already adopted and implemented Windows 10. So far, so good - but the experiences from the field and big threats like WannaCry still demonstrate that many companies have massive trouble in servicing Windows 10. Either some of them simply overengineer the whole process by putting way too much effort into application testing repeatedly or they just give up and let everything happen. In my session, I will show you what my experiences have been. What you should consider and what is just overhead. We will talk about deployment tweaks of Configuration Manager, Application Compatibility, the management process of updates , Upgrade Readiness and how Windows Analytics can help.

1. Windows 10 Servicing -
the do’s and don'ts
Alexander Benoit
Head of Competence Center Microsoft @sepago
@ITPirate

2. Alexander Benoit
Senior Consultant / Head of Competence Center Microsoft
„Future Workplace“, Security
SCCM, Intune, Windows 10, Defender Framework,…
Alexander.Benoit@sepago.de
@ITPirate
http://it-pirate.com/

3. Basics
Windows Servicing

4. Update evolution
With Windows 7 and 8, servicing choices added complexity and cost,
increased fragmentation, and reduced quality
Cumulative
Updates
Typical Windows 7 PC:
Selectively Patched
Windows 7 Test Lab PC:
Fully Patched
What you were
running
What software
developers are
testing
Y
YY

5. Update evolution
Cumulative
Updates

6. With Windows 10 servicing, consistency and simplicity
are paramount
• A single cumulative update each month
• Security fixes, reliability fixes, bug fixes,
etc.
• Supersedes the previous month’s update
• No new features
• Try them out with Security Update
Validation Program (SUVP), other
• Very reliable, with built-in rollback
capabilities
• Simple deployment using in-place
upgrade,
driven by existing tools
• Try them out with Insider Preview
Quality Updates Feature Updates

7. Broad Deploy
Stage broad deployment
Information workers
General population
Long Term
Servicing Channel
Deploy for mission critical
systems
Specialized systems
Specific feature and
performance feedback
Application compatibility
validation
Windows Insider
Preview Branch
Test machines, small pilots
Targeted Deploy
Deploy to appropriate audiences
Test and prepare for broad
deployment
Early adopters, initial
pilots, IT devices
STAGE
NUMBEROFDEVICES
Release
Thinking through deployment strategy

8. Windows as a Service
Windows 10 1709
Windows 10 1803
Windows 10 1809
Windows 10 1703
2017 2018 2019 2020
Pilot BroadPlan &
Prepare
18 months for each release

9. Windows Update as a Service
Release Thinking
Agile Thinking

10. Project Communication
• IT / Infrastructure
• Application holder
• Management
• Client Team
• IT Security
• Data Privacy Team
• “Betriebsrat”
Communi
cation is key!

11. Process
Procedural
Changes

12. High
Level
Getting
ready
OS
Version
Migration
Preparations
Remediations
Decisions
Communication
RemainingSteps

13. Process
Windows as
a Service is
also a
mind
change

14. Release Thinking / Waterfall Model
New Client
Documen
tation
Outsourcing
Complete
Testing
Client
Release
One version of Windows
in Deployment
Single complete
Testing
Release Deployment

15. Agile Model
Develop
Test
User Acceptance
Testing
Pre-Production
Production
Several Versions of
Windows 10 in Deployment
Continuous Testing
Continuous Deployment

16. Explanation Awareness
PreparationImplementation
WaaS Cycle
21
34

17. Branches
Feature and Quality
Updates
Timelines
Managing
High Level
Explanation
Explanati
on
Awarenes
s
Preparati
on
Implementa
tion

18. Showing WaaS
Complexity in the
Enterprise
Compatibility
Procedural changes
Technological
requirements for
implementation
Awareness
Explanati
on
Awarenes
s
Preparati
on
Implementa
tion

19. Application list with all
information
Plan for procedural and
technological changes
Process for Application
Incompatibility
Defining Deployment
Strategy
Preparation
Explanati
on
Awarenes
s
Preparati
on
Implementa
tion

20. Action plan
Implementing
process
Technical
implementation
Further steps
Implementation
Explanati
on
Awarenes
s
Preparati
on
Implementa
tion

21. Procedural Approaches
Windows Servicing

22. Pilot Broad
2017 2018 2019
Windows as a Service
Skipping possible?
2020
18 months for each release
Windows 10 1709
Plan &
Prepare
Windows 10 1803
Windows 10 1809
Windows 10 1703
Upgrade Machine
Nearly no time buffer

23. Pilot Broad
2017 2018 2019
Windows as a Service
Automation?
2020
18 months for each release
Windows 10 1709
Plan &
Prepare
Windows 10 1803
Windows 10 1809
Windows 10 1703
Broad +10d
Broad +10d
Broad +10d
Broad +10d

24. ▪ Application Holder
▪ Accountability
▪ Test User
▪ Manual / Automatic Testing
▪ Possibly different
Timeframes
▪ Feedback
Decentralized Testing Approach
Central IT
Key-Users
Application
holder
Test-User 1
SACT
Test-User 2
SACT + d
Test-User n
SAC
Automated /
Manual
Testing

25. Windows as a Service
Automation?

26. WaaS – Granular View for one Release
Phase Broad DeployPlan & Prepare
Buffer for Upgrade /
Compliance Cleanup
Insider
Preview
State
6 months 18 months
Windows 10 1803
Semi Annual Channel (Targeted) Semi Annual Channel
approx. 4 months approx. 14 months
Targeted Deploy
OS Release Ready for Broad
Deployment

27. ▪ Plan & Prepare = Insider Preview = IP = 6 months
▪ Targeted Deploy = Semi Annual Channel (Targeted) = SACT = approx. 4 months
▪ Broad Deploy = Semi Annual Channel = SAC = approx. 14 months
▪ SACT + SAC = the time this OS Release is supported = 18 Months
▪ Buffer for Upgrade = Compliance Cleanup = approx. 4 months
Legend and Facts

28. Recurring Procedural Steps
Who
• Project Teams
• Users
• User Groups
What
• Tasks
• Steps
• Checks
Starting Time Point
• Relative (Event based)
• Absolute (Date based)
Working Time Frame
• Relative (Event based)
• Absolute (Timespan based)
Finishing Date
• Relative (Event based)
• Absolute (Date based)
Outcome
• Information (e.g. Prerequisites)
• Configuration Set (GPOs)
• Accomplished Tasks
• New Tasks / Roadmap

29. Recurring Procedural Steps – Demo 1
Who • Project Team
What • Validate new Features
Starting Time
Point
• [Absolute] 2 Months before OS Release in February
Working Time
Frame
• [Absolute] 4 Weeks after Start
Finishing Date • [Absolute] 1st July / 1st November
Outcome
• [Information] What features should be used? What
are the Prerequirements?
• [Tasks] Are any features planned to target later
releases?

30. Recurring Procedural Steps – Demo 2
Who • Project Team
What • Validate new Features
Starting Time
Point
• [Event] Feature closing
Working Time
Frame
• [Event] ASAP till OS Release
Finishing Date • [Event] OS Release
Outcome
• [Information] What features should be used? What
are the Prerequirements?
• [Tasks] Are any features planned to target later
releases?

31. Retrieving Procedural Steps
Brainstorming
for all Tasks
Removing
unnnecessary
Tasks
Setting Who,
What and the
Outcome
Choosing
between
Date-based
and
Event-based
for each time
Visualizing
the Tasks in
Timeline for
one complete
Release
Defining Starting Time Point,
Working Time Frame
and Finishing Date with
Visualization
Share
Complete List
Fine-tuning

32. TimeTrigger
Plan & Prepare Targeted Deploy Broad Deploy
Collection
OS Release Ready for Broad
Compliance
Cleanup
UpgradeReactive Testing & ProductionProactive Testing
Automation of Servicing with Rings

33. Plan & Prepare Targeted Deploy Broad Deploy
Automated SelectionSemi-manual SelectionManual Selection
Planning Ring Counts
1 - 3 3 - 12 5 - 40
Cleanup
2 - 4
Auto

34. Targeted Deploy
Targeted Deploy
OS Release Ready for Broad

35. https://blogs.msdn.microsoft.com/daviddasneves/2017
/08/12/automating-windows-as-a-service/
Automating Windows
as a Service

36. Windows Analytics
Windows Analytics
A suite of tools

37. Windows Analytics
A suite of tools
Plan upgrades by identifying
devices that are ready and identify
and resolve top app/driver compat
blockers.
Ensure update and antimalware
compliance with timely reports
for all your devices (even those
on the road).
Reduce support costs by
proactively identifying and
remediating top end-user
impacting issues.

38. Upgrade Readiness
Windows Analytics
Ensuring Windows 10 is up to date

39. Allows IT to . . .
▪ quickly identify and focus on critical issues
impeding upgrades.
▪ get data-driven insights to plan and
manage upgrades end to end.
Upgrade Readiness provides . . .
▪ workflow visualization from pilot to
deployment.
▪ powerful upgrade readiness insights and
recommendations about computers,
applications, and drivers.
▪ a risk-based approach to app
rationalization.
▪ Microsoft guidance on app and driver
compatibility issues.
Upgrade Readiness

40. Collect details
• Apps
• Drivers
• Office add-ins
• Web pages
Find known issues from
compatibility database
• Detected by
Microsoft or
reported by ISVs
• Workarounds,
remediation steps
Match with
Ready for Windows
data
• Support statements
• Broad usage
information
Upgrade Readiness:
Combining data sources

41. Ready for Windows
A clear view for ISV apps:
• ISV support statements for Windows 10
• App installation data from the broad set
of Windows 10 devices
App Status Guidance
Adopted This application has been installed on at least 10,000 commercial
Windows 10 devices.
Highly adopted This application has been installed on at least 100,000
commercial Windows 10 devices.
Supported version
available
The ISV has declared support for a version of this application on
Windows 10.
Contact software
provider
There may be compatibility issues with this solution, and thus
Microsoft recommends contacting the software provider to learn
more.