This document outlines the steps for planning a large-scale deployment of Windows 10 and Office 365 ProPlus. It discusses assessing device and application readiness, preparing directory and network infrastructure, deploying Office and line-of-business apps, migrating user files and settings, implementing security and compliance capabilities, deploying OS updates, establishing processes for ongoing feature updates, and training users. The goal is to provide guidance on effectively transitioning from older desktops to a modern desktop-as-a-service model.

1. Microsoft 365
Training Series:
Modern Desktop
Deployment

2. Planning a modern desktop
deployment
Chris Rhodes MVP
IT Masterclasses.com
Chris@itmasterclasses.com

3. ‘How to shift’
to a modern
desktop
Core steps and processes for large-
scale deployment of Windows 10 and
Office 365 ProPlus

4. Why move?
END-TO-END IMPROVEMENTS FOR
SECURITY AND INFORMATION
PROTECTION
TEAMWORK AND PRODUCTIVITY
ENHANCEMENTS CONNECTED WITH
OFFICE 365
AND IF YOU’RE STILL ON WINDOWS 7
OR OFFICE 2010, SUPPORT ENDS
STARTING JANUARY 2020

5. What’s
different
compared to
the last big
desktop
deployment?
Directory services are moving to the cloud as the fabric for
connecting to cloud-based services across apps and services
In-place upgrades are viable and recommended for applying new
versions of Windows
UEFI replaces the traditional BIOS and is needed along with 64-bit for
many of the modern security and protection capabilities in Windows
Microsoft Intune can manage Windows 10 policies, your connected
apps and be configured for co-management with ConfigMgr
Office 365 ProPlus is the preferred option of Office desktop apps and
uses a new package type called Click-to-Run
Office 365 ProPlus and Windows 10 are now use semi-annual feature
updates and cumulative monthly updates

6. Thinking
through the
deployment
process

7. Device and App
Readiness
• Inventory devices and apps under management
• Prioritize devices and apps based on counts and
importance
• Windows Analytics Upgrade Readiness helps assess apps
and devices against known compatibility status
• Work through hardware and app inventory and use info to
target devices ready for deployment
• Continue triaging and expanding target devices until
deployment is complete
• Work with Desktop App Assure via Microsoft FastTrack
• Implement required fixes for browser-based apps
Windows Analytics

9. Windows Analytics

10. Coming soon: Desktop Analytics

11. Integration with ConfigMgr Deployment

12. Directory and
Network Readiness
• Azure Active Directory deployed for targeted users
• Network bandwidth requirements calculated for OS,
apps, drivers, language packs and user state
• Delivery Optimization, P2P caching, LEDBAT and
compression controls configured to control bandwidth
• Plan Office-related networking considerations:
OneDrive Known Folder Move, Outlook Data Files, etc.
• Deployment rings and group phases planned based on
readiness and network capacity

13. SCCM Peer Cache Config
Peer to Peer Cache Options in ConfigMgr

14. Throttling without LEDBAT

15. Throttling with LEDBAT

16. Enabling LEDBAT In ConfigMgr

17. Office & LOB App
Delivery
• Ensure required apps are available for managed
software distribution
• Prepare new apps to replace or supersede apps
that won’t be brought forward
• Prepare for Office 365 ProPlus (Click-to-Run)
app delivery, customization and user-based,
subscription activation

18. New Office Customization Tool in ConfigMgr

19. User Files & Settings
• Target scenarios where user state migration is required: PC
replacement or wipe and load
• Plan for methods to be used: OneDrive Known Folder
Move, User State Migration Tool or custom solution
• Prepare required storage infrastructure

20. OneDrive Known Folder Move

21. OneDrive Known Folder Move

22. Security & Compliance
• Assess current client-side and server or cloud-based
security solutions in place
• Test impacts of 3rd party disk encryption and anti-malware,
then plan your deployment and AV software accordingly
• Plan for new security and compliance capabilities in
Windows 10 and Office 365 ProPlus
• Assess security considerations of deployment process,
access to deployment shares and how user state is migrated
• Configure endpoint settings and policies: Group Policy,
MDM, Data Loss Prevention
• Configure security and compliance services for cloud-based
components and EDR

23. …or fingerprint login
Windows Hello Password-less Authentication

24. Cloud attach with ConfigMgr

25. OS Deployment &
Feature Updates
• Assess hardware replacement cycle
• Prepare hardware and application testing for each new feature
update, verify hardware vendor support for each feature
update
• Plan for in-place upgrades for Windows 10 releases, refresh,
replace and bare metal deployments for Windows 7 to
Windows 10
• Establish deployment plan with validation feedback loop
• Establish process for rollback, remote users or no
infrastructure deployment scenarios (offline media)
• Carry out deployment plan and establish repeatable process
for new users and ongoing PC replacements

26. ConfigMgr Upgrade Task Sequence Template

27. Windows Autopilot for existing PCs Task Sequence

29. Windows- &
Office-as-a-Service
• Prepare for semi-annual feature updates to Office
and Windows
• Establish Insider team and process to evaluate new
Windows and monthly Office updates
• Prepare for updates to software distribution and
update management tools as needed
• Operationalize semi-annual deployment processes

30. Semi-annual channel support
0
6
12
18
24
30
1607-1803 (all) Future **09, starting 1809 Future **03, starting 1903 Office 365 ProPlus
Months of support from release date
Windows 10 Office 365 apps

33. User Comms &
Training
• Plan for user communications to inform on
timing and actions
• Communicate and train users on new
capabilities, new ways to work and other
updates – leverage Productivity Library
templates and services via Microsoft FastTrack
and Microsoft IT Showcase
• Set up usage goals, programs and monitoring

34. aka.ms/ProductivityLibrary

35. aka.ms/Win10ITShowcase

36. Tracking Usage via Office 365 Admin Center

37. microsoft.com/FastTrack

38. Modern Desktop
Deployment Resources

39. Next Steps
Help IT Pros and Partners
find and use How to Shift
Guidance
aka.ms/HowToShift

40. aka.ms/howtoshift

41. aka.ms/HowToShift

42. Desktop Deployment
Essentials on Mechanics
aka.ms/WatchHowToShift

43. Dedicated Desktop Deployment Essentials
aka.ms/WatchHowToShift

44. New labs: OneDrive Known Folder Move, ConfigMgr Windows 7 to
Windows 10 migration, Upgrade Sequences, Network Optimization, and
new Office Customization Tool for Click-to-Run
aka.ms/HowToShiftLabs

45. New labs: OneDrive Known Folder Move, ConfigMgr Windows 7 to
Windows 10 migration, Upgrade Sequences, Network Optimization, and
new Office Customization Tool for Click-to-Run
aka.ms/HowToShiftLabs

46. Microsoft FastTrack
for Office 365 ProPlus
51k+800+ 4k+
22k+ 4.1M+3.7 PB
Realize business value faster
Customer success service included with your subscription*
Ongoing expert assistance from 800+ FastTrack engineers**
Service onboarding and user adoption planning
Application compatibility assessments using Office Telemetry***
Methodology &
Resources
Tools &
Insights
Experts
Plan for a
successful
rollout
Move to Office
365 with
confidence
Boost user
engagement