Office 365 Deployment Lessons from the Field: The Good, the Bad and the Ugly Glen Gooda Senior Consultant OSP334

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 Lots of choices….. Simple co-existence, Cloud IDs…. On-premises, hybrid, all cloud… ADFS…. DirSync… Where to begin??  Multiple Outsourcers  Highly Complex Environment  Multinational does not equal to a large project team…  Also does not equal to a skilled team  Do you have buy in from BU’s to deploy.  Is deployment shifting to a PoC?  Does Corp IT know what’s the case on the ground, site readiness?  PF’s, Networking, Desktop’s, User Profiles?  Setup Process  Existing FOPE customer  Rename the tenant  Need a lab environment?

 Networking, AD, Messaging, ADFS, Security, Helpdesk etc.  No Deployment Project Manager or program Manager  No clear Executive Sponsor  Authentication change for Outlook Clients  New URLs, settings and capabilities  Internal stakeholders, and disaster response teams  Going Office 365 does not resolve a Basic / fighting fires environment…. It can exacerbate it  Customer Maturity to Accepting Change in the Service. i.e. Its never seamless….  It’s a Service versus a Product  Re-Educate yourself and be prepared to adopt a much faster rate of change than you may have been accustomed to

10 Onboarding Milestones at a Glance

 Office 365 Service Descriptions provide descriptions for the components of the suite. Office 365 Service Descriptions  Microsoft Office 365 Deployment Guide (MODG) is intended to help you understand the requirements and workflows for on boarding your organisation to Microsoft Office 365 enterprise plans. Microsoft Office 365 Deployment Guide (MODG)  The Office 365 Service Alignment Indicator (OAI) tool can also help identify the specific areas where your business requirements do not align with the Office 365 service offering.  The Exchange Deployment Assistant to give a basis for ‘As Built’ type documentationExchange Deployment Assistant

 Know what your current provisioning and de- provisioning processes are… Have they changed?  Do users understand Office applications? Are they getting a new version?  How will the Admin and Service Desk role change? What new skills do they need?  Get posters and quick start guides out – generate excitement  Communications before, during and after….

 Only implement features you really need  Clear understanding of whether Cloud IDs or Federated identities will be deployed  Do you need co-existence and for how long?  Co-existence mail flow requirements clearly defined  Clear understanding on whether Directory Synchronisation will be deployed  A hybrid deployment with Exchange 2010 requires two CAS servers for load balancing and redundancy  Single Sign On requires two or more ADFS backend and proxy servers

 Will your trial tenant be converted into your production tenant or thrown away?  Carefully choose the tenant name as they will appear in Lync Invites and SharePoint  There are no tools to rename or migrate data from one tenant to another  If you have more than 50,000 objects connect Microsoft Support before signing up for a production tenant  Are you already using FOPE standard? Will you migrate the namespace to Office 365?

 All proxy servers and NAT devices identified and remediated  Access to manage internal and External DNS records  Bandwidth upgrades implemented based on estimated network loads  The Microsoft Online Deployment Guide is your friend! Adding a Domain to Office 365 External DNS Records Third-party SSL Certificates Ports and Protocols Firewall Considerations Proxy Device Considerations WAN Accelerators Hardware and Software Load-balancing Devices Internet Bandwidth Planning

 All AD remediation that was identified by the Office 365 Deployment Readiness Tool (DRT has been completedOffice 365 Deployment Readiness Tool (DRT  Do UPN’s need to be updated to externally routable namespaces?  No  All duplicate attributes remediated  ProxyAddresses  UPNs  Primary SMTP addresses

 Decisions made on large mailboxes – Delete / Archive / Migrate  Mailbox migration speed tested  Small mailboxes <100MB  Medium mailboxes MB  Large mailboxes GB or above  As latency increases mailbox migration throughput slows  Do you need regional MRS or Outlook Anywhere endpoints?  Groups created for migration batches  Geographical  Business Unit  Based on relationships  Manager and PA  Generic Helpdesk mailbox and Service Desk staff

Existing organisation Number of mailboxes to migrate Do you want to maintain mailboxes in your on- premises organisation? Deployment option Exchange 2010, Exchange 2007 or Exchange 2003 Less than 1,000 mailboxesNo Cutover Exchange migration Exchange 2007 or Exchange 2003 No maximumYes Staged Exchange migration or hybrid deployment Exchange 2010 More than 1,000 mailboxes NoHybrid deployment Exchange 2010 More than 1,000 mailboxes YesHybrid deployment Office 365 for professionals and small businesses Fewer than 50 *Not applicable ** Cutover Exchange migration maximumYes Staged Exchange migration or IMAP migration Exchange 2000 Server or previous versions No maximumYesIMAP migration Non-Exchange on- premises messaging system No maximumYesIMAP migration

 Hardware sizing based on current usage profiles and ordered  High Availability requires  2 x Exchange 2010 CAS/HT Servers and a load balancer  Redundant ADFS configuration  Third party certificates bought and ordered  Directory Synchronisation healthy  Trust has been established with the Microsoft Federation Gateway:  All required SMTP domains have been verified in Office 365  Exchange Web Services have been published on premises: aspx aspx  Exchange Server 2010 (SP2) license for Hybrid deployment: online- .aspx online- .aspx

 Healthy and reliable software delivery mechanism e.g. SCCM  Mail enabled applications identified and tested  Line of business applications tested  Computers pre-emptively updated with Software and web browser requirements for Office 365Software and web browser requirements for Office 365  May have enlisted the help of Desktop Deployment Planning Services (DDPS)Desktop Deployment Planning Services (DDPS)  Software Assurance Planning Services Provider website Software Assurance Planning Services Provider website

 Common server-side applications include:  Mobile device synchronization services, such as Research in Motion BlackBerry® Enterprise Server  Inbound/outbound Fax solutions  Message Scanning, Hygiene solutions  Data Leakage protection solutions  Mail Routing extensions  What about Multi-function devices?  What about bulk mailing applications?

OSP331 – Office 365 Voice of the Customer Exchange Deployment Assistant OSP212 – Introducing Office 365 for Enterprises OSP224 – Office 365 Identity Federation Technology Deep Dive EXL311 – Exchange Server 2013 Architecture Deep Dive