5. Admin: Simple to provision and configure Policy driven via Transport Rules Customizable branding of encrypted emails and mail reading portal Allows for Enterprise content inspection and compliance Sender: Ability to send encrypted messages to any SMTP address regardless of recipient’s client or service provider Recipient: View encrypted messages on Office 365 Message Encryption portal after sign-in Office 365 Message Encryption portal has rich OWA controls for viewing and composing messages Replies from the portal are also encrypted

6. How do recipients sign-in to view messages? – 2 ways Microsoft account – used for sign-in to Microsoft services like OneDrive, XBOX Live, etc… Microsoft account for hotmail.com, outlook.com, live.com already exists User can create Microsoft account for any SMTP address, like gmail.com, mycustomdomain.com – address verification done as part of account creation process If recipient does not have a Microsoft account, recipients are navigated through the process of creating one For a given email address, a single Microsoft account is used to access all Microsoft services and view future encrypted emails Organizational Account – used for sign-in to workloads like Exchange Online, SharePoint Online, etc… As Office 365 embraces additional identity providers, so will Office 365 Message Encryption.

8. New ETR actions configurable via UI or PowerShell New-TransportRule –Name EncryptRule -ApplyOME $true New-TransportRule –Name DecryptRule -RemoveOME $true

9. Customize opening text in encrypted email and disclaimer statement Set-OMEConfiguration -Identity default -EmailText "Encrypted message from ContosoPharma secure messaging system" Set-OMEConfiguration -Identity default -DisclaimerText “This email message and its attachments are for the sole use of the …"

10. Set-OMEConfiguration -Identity default -PortalText "ContosoPharma secure e-mail portal" Set-OMEConfiguration -Identity default -Image (Get-Content "C:\Users\admin\Desktop\contoso.png” -Encoding byte)

12. Exchange Online Policy detection and Enforcement Tenant configuration O365 UserInternet User Send Microsoft account/Organization Account Mail Reading Portal Deliver Post

13. Office 365 Message Encryption uses IRM as a platform to encrypt message Sending organization needs to have purchased and configured Azure Rights Management Services (RMS) Keys imported from Azure RMS are 2048 bit and use SHA-256 encryption Encrypted messages are wrapped in an HTML file and sent as an attachment to intended recipients HTML file contains the encrypted message along with other metadata Messages can be viewed on any device that can open and post from an HTML file When user opens and clicks on link in the attachment, encrypted content is posted and held temporarily while user authenticates User authenticates using a Microsoft account or Organizational Account If user has neither, user is told and asked to create a Microsoft account before viewing Any email address (@yahoo.com, @gmail.com, etc…) can be used to create a Microsoft account Once the authentication completes, message is decrypted and shown in modern UI with all rich OWA controls Messages replied from the portal are also encrypted

14. Office 365 Message Encryption is included with Azure RMS * On-premise customers need to route mails through Exchange Online ** Windows Azure Rights Management is not available for Office 365 Small Business plans PlanRequiresPrice Office 365 E3, E4Windows Azure Rights Management is includedIncluded Office 365 E1, K1Windows Azure Rights Management$2 PUPM Office 365 Exchange Online Plan 2, Plan 1, KioskWindows Azure Rights Management$2 PUPM Office 365 SharePoint Plan 2, Plan 1Windows Azure Rights Management$2 PUPM Office 365 Midsize BusinessWindows Azure Rights Management$2 PUPM Exchange on-premisesWindows Azure Rights Management$2 PUPM

15. Customers using EHE will be upgraded to Office 365 Message Encryption at no additional cost Awareness and transition emails will be sent prior to transition – Transitions started for Q1CY14 No action required on tenant admins – existing EHE policies will be automatically migrated to Office 365 Message Encryption policies EHE mail recipients will continue to have access to view their old encrypted emails EHE account store and emails already encrypted with EHE will not be migrated to Office 365 Message Encryption

16. FeatureExchange Hosted EncryptionOffice 365 Message Encryption Send Encrypted Mail to anyoneAvailable Custom BrandingNot AvailableAvailable Message attachment size limit10 MB25 MB Integration with Exchange transport rules Available, but complex headers involved Available and simplified User experienceCustom EHE portalEnhanced Office 365 UI Integration with Data Loss PreventionAvailable Purchase OptionSold StandaloneIncluded with Azure RMS

17. Information Protection technology Protection is persisted with the data, content can travel anywhere (desktops, file shares, USB keys, cloud drives, network and devices) Combines encryption and usage restrictions Prevent accidental disclosure of sensitive data by applying usage polices (cannot forward, cannot print, read-only) Simple to use Authors just select a policy option, consumers just open documents Administrators can configure policies to protect content automatically Securely share data with individuals within organization and trusted partners

18. Admin: Simple to provision and configure using Windows Azure Rights Management – No on-premises RMS server required Policy driven via Transport Rules Allows for Enterprise content inspection and compliance Sender: Ability to send IRM protected messages to recipients in the organization using supported clients - OWA and Microsoft Office 2010 and 2013 Recipient: Ability to view IRM protected content just like regular emails using supported clients (OWA, Microsoft Office 2010 and 2013, EAS)

19. Automatically protect email with IRM using Exchange Transport Rules

20. Protect email with IRM right from the Outlook Web App.

21. Government preferred way to secure email communication Based on a published and broadly supported standard Must know recipients public cert to send them encrypted mail Must have private key associated with sending email address to sign email Without having recipients private key, no one can open and view the message Exchange on-prem continues to support S/MIME OWA 2013 support added in SP1

23. Admin Exchange Online configuration options