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Experts Live Europe 2017 - Windows 10 Servicing - the do’s and don'ts

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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.

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Experts Live Europe 2017 - Windows 10 Servicing - the do’s and don'ts

  1. 1. Windows 10 Servicing - the do’s and don'ts Alexander Benoit Head of Competence Center Microsoft @sepago @ITPirate
  2. 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. 3. Basics Windows Servicing
  4. 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. 5. Update evolution Cumulative Updates
  6. 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. 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. 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. 9. Windows Update as a Service Release Thinking Agile Thinking
  10. 10. Project Communication • IT / Infrastructure • Application holder • Management • Client Team • IT Security • Data Privacy Team • “Betriebsrat” Communi cation is key!
  11. 11. Process Procedural Changes
  12. 12. High Level Getting ready OS Version Migration Preparations Remediations Decisions Communication RemainingSteps
  13. 13. Process Windows as a Service is also a mind change
  14. 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. 15. Agile Model Develop Test User Acceptance Testing Pre-Production Production Several Versions of Windows 10 in Deployment Continuous Testing Continuous Deployment
  16. 16. Explanation Awareness PreparationImplementation WaaS Cycle 21 34
  17. 17. Branches Feature and Quality Updates Timelines Managing High Level Explanation Explanati on Awarenes s Preparati on Implementa tion
  18. 18. Showing WaaS Complexity in the Enterprise Compatibility Procedural changes Technological requirements for implementation Awareness Explanati on Awarenes s Preparati on Implementa tion
  19. 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. 20. Action plan Implementing process Technical implementation Further steps Implementation Explanati on Awarenes s Preparati on Implementa tion
  21. 21. Procedural Approaches Windows Servicing
  22. 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. 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. 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. 25. Windows as a Service Automation?
  26. 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. 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. 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. 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. 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. 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. 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. 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. 34. Targeted Deploy Targeted Deploy OS Release Ready for Broad
  35. 35. https://blogs.msdn.microsoft.com/daviddasneves/2017 /08/12/automating-windows-as-a-service/ Automating Windows as a Service
  36. 36. Windows Analytics Windows Analytics A suite of tools
  37. 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. 38. Upgrade Readiness Windows Analytics Ensuring Windows 10 is up to date
  39. 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. 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. 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.

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