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As you already know Exchange Server 2016 will be entering Extended Supporton October 14th 2020.. During that period it will receive only Critical and will be no further release of CUs, with the last planned CU to be released in December 2020. One of the many concerns regarding that transition is that at the moment there is no free Exchange Server 2019 license for just managing the exchange attributes on hybrid deployments as there is for Exchange 2016. According to the Product Group that specific license for the Exchange Server 2019 will be release after 14th October. Also as a heads-up the product group is working on a solution that will remove the need of those on-premise “management attributes| only servers. Microsoft encourages Exchange Server 2016 customers to adopt CU19 as soon as possible to ensure uninterrupted delivery of any future security related fixes. After December 15, 2020, only CU19 or its successors will receive critical updates. During the Extended Support phase, only the latest CU is eligible to receive critical updates once the standard 3 month transition period of the prior CU has lapsed. Critical updates will continue to be made available via Windows Update and the Microsoft Download Center. Additional lifecycle information for all Microsoft products is available on docs.microsoft.com. These are great news since is the first time that a working plan for the retirement of those on-premise server serving only for management is announced.

This cumulative update is a security update. It includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues Cumulative Update 6 for Microsoft Exchange Server 2019 was released on June 16, 2020. This cumulative update is a security update. It includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. These fixes will also be included in later cumulative updates for Exchange Server 2019. This update also includes new daylight saving time (DST) updates for Exchange Server 2019. For more information about DST, see Daylight Saving Time Help and Support Center. Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. NotesIf you are upgrading from Cumulative Update 2 for Exchange Server 2019 or a later cumulative update for Exchange Server 2019 to Cumulative Update 6 for Exchange Server 2019, there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you have ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 2 for Exchange Server 2019), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD commandis run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages. To avoid the errors, either the user should join Schema Admins and Enterprise Admins groups or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then, the Exchange admin user can start Setup. Autodiscover Event ID 1 occurs after you install Cumulative Update 3 for Exchange Server 2019. For more information, see KB 4532190. Issues that this cumulative update fixes This cumulative update also fixes the issues that are described in the following Microsoft Knowledge Base articles: 4559441 Foreign language characters set in RejectMessageReasonText of a transport rule aren’t shown correctly in Exchange Server 2019 4547707 Enable piping for Restore-RecoverableItems in Exchange Server 2019 4549689 HMA EvoSTS certificate rollover causes authentication prompts due to stalled key on worker process spawn (warmup phase) in Exchange Server 2019 4559446 Changes to Outlook on the web blocked file extensions and MIME types in Exchange Server 2019 4559440 Export to a PST for an eDiscovery search fails Exchange Server 2019 4559439 EAS creates failure report if a message with unknown recipients is in Drafts in Exchange Server 2019 4559442 2080 Events caused by empty values in HKLM\SYSTEM\CurrentControlSet\Services\MSExchange ADAccess\Instance0 in Exchange Server 2019 4559438 Edge Transport server hangs in Exchange Server 2019 4559443 Managed Folder Assistant fails with Event ID 9004 NotInBagPropertyErrorException in Exchange Server 2019 4559437 PR_RECIPIENT_ENTRYID is computed if no email address or type in Exchange Server 2019 4559444 Conversion from HTML to RTF removes non-breaking space in Exchange Server 2019 4559436 Attachments with properties (like Azure Information Protection labels) not always matching in Exchange Server 2019 4559435 Introduce an OrganizationConfig flag to enable or disable recipient read session in Exchange Server 2019

This cumulative update includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. Notes If you are upgrading from Cumulative Update 13 for Exchange Server 2016 or a later cumulative update for Exchange Server 2016 to Cumulative Update 17 for Exchange Server 2016, then there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you have ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 13 for Exchange Server 2016), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD command is run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages.To avoid the errors, either the user should join Schema Admins and Enterprise Admins groups or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then the Exchange admin user can start Setup. Autodiscover Event ID 1 occurs after you install Cumulative Update 14 for Exchange Server 2016. For more information, see KB 4532190. Issues that this cumulative update fixes This cumulative update fixes the issues that are described in the following Microsoft Knowledge Base articles: 4559444 Conversion from HTML to RTF removes non-breaking space in Exchange Server 2016 4559435 Introduce an OrganizationConfig flag to enable or disable recipient read session in Exchange Server 2016 4547707 Enable piping for Restore-RecoverableItems in Exchange Server 2019 and 2016 4559436 Attachments with properties (like Azure Information Protection labels) don’t always match in Exchange Server 2016 4559437 PR_RECIPIENT_ENTRYID is computed if no email address or type in Exchange Server 2016 4559438 Edge Transport server hangs in Exchange Server 2016 4559439 EAS creates failure report if a message with unknown recipients is in Drafts in Exchange Server 2016 4559440 Export to a PST for an eDiscovery search fails in Exchange Server 2016 4559441 Foreign language characters set in RejectMessageReasonText of a transport rule aren’t shown correctly in Exchange Server 2016 4559442 2080 Events caused by empty values in HKLM\SYSTEM\CurrentControlSet\Services\MSExchange ADAccess\Instance0 in Exchange Server 2016 4549689 HMA EvoSTS certificate rollover causes authentication prompts due to stalled key on worker process spawn (warmup phase) in Exchange Server 2016 4559443 Managed Folder Assistant fails with Event ID 9004 NotInBagPropertyErrorException in Exchange Server 2016 4559446 Changes to Outlook on the web blocked file extensions and MIME types in Exchange Server 2016

This cumulative update is a security update. It includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues Κnown issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. NotesIf you are upgrading from Cumulative Update 2 for Exchange Server 2019 or a later cumulative update for Exchange Server 2019 to Cumulative Update 5 for Exchange Server 2019, there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you have ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 2 for Exchange Server 2019), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD commandis run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages. To avoid the errors, either the user should join Schema Admins and Enterprise Admins groups or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then, the Exchange admin user can start Setup. Autodiscover Event ID 1 occurs after you install Cumulative Update 3 for Exchange Server 2019. For more information, see KB 4532190. Issues that this cumulative update fixes This cumulative update also fixes the issues that are described in the following Microsoft Knowledge Base articles: 4552472 Exchange Server 2019 Sizing Calculator version 10.4 is available 4536552 Export-ModernPublicFolderStatistics.ps1 is not working in Exchange Server 2019 4538303 Exchange 2019 Setup Prerequisite Check fails for .NET 4.8 Framework in CU4 on Windows builds 1909 and 1903 4547705 Authentication loop between msft.sts.microsoft.com/adfs and OWA in Exchange Server 2019 4547706 Birthday isn’t correctly synced to iOS native mail app in Exchange Server 2019 4547708 Elevation of privileges possible when Active Directory permissions role is granted in Exchange Server 2019 4547709 InternetWebProxyBypassList is ignored by Mailbox Replication service in Exchange Server 2019 4547710 New-MailboxSearch with In-Place Hold enabled replaces all values in msExchUserHoldPolicies if adding a value in Exchange Server 2019 4547711 Public folder permissions aren’t applied from Outlook in Exchange Server 2019 hybrid environment 4547712 Outlook on the web (OWA) exposes junk operations even if disabled via OwaMailboxPolicy in Exchange Server 2019 4547713 IsOnlineMeeting is always false for Teams-only meetings in Exchange Server 2019 4547714 Can’t add remote shared mailbox using ECP into distribution group in Exchange Server 2019 hybrid environment 4547715 New created search folder retention policy is changed in Exchange Server 2019 4547719 MCDB status is “Offline” and SSDs are not formatted in Exchange Server 2019 4547720 Partial word searches not working for mailboxes in Outlook online mode in Exchange Server 2019 4547721 Exchange Sizing Calculator still supports mail.que database over 2 TB in Exchange Server 2019 4547722 Can’t go from Office 365 to Enterprise in Exchange Server 2019 Exchange admin center (EAC) if Chrome SameSite Cookie is enabled 4547723 Can’t sign in to Office 365 if configuring hybrid with Chrome SameSite Cookie enabled in Exchange Server 2019 4536987 Description of the security update for Microsoft Exchange Server 2019: February 11, 2020 4540123 Description of the security update for Microsoft Exchange Server 2019: March 10, 2020

This cumulative update includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. Notes If you are upgrading from Cumulative Update 13 for Exchange Server 2016 or a later cumulative update for Exchange Server 2016 to Cumulative Update 16 for Exchange Server 2016, then there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you have ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 13 for Exchange Server 2016), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD command is run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages.To avoid the errors, either the user should join Schema Admins and Enterprise Admins groups or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then the Exchange admin user can start Setup. Autodiscover Event ID 1 occurs after you install Cumulative Update 14 for Exchange Server 2016. For more information, see KB 4532190. Issues that this cumulative update fixes This cumulative update fixes the issues that are described in the following Microsoft Knowledge Base articles: 4547705 Authentication loop between msft.sts.microsoft.com/adfs and OWA in Exchange Server 2016 4547706 Birthday isn’t correctly synced to iOS native mail app in Exchange Server 2016 4547708 Elevation of privileges possible when Active Directory permissions role is granted in Exchange Server 2016 4547709 InternetWebProxyBypassList is ignored by Mailbox Replication service in Exchange Server 2016 4547710 New-MailboxSearch with In-Place Hold enabled replaces all values in msExchUserHoldPolicies if adding a value in Exchange Server 2016 4547711 Public folder permissions aren’t applied from Outlook in Exchange Server 2016 hybrid environment 4547712 Outlook on the web (OWA) exposes junk operations even if disabled via OwaMailboxPolicy in Exchange Server 2016 4547713 IsOnlineMeeting is always false for Teams-only meetings in Exchange Server 2016 4547714 Can’t add remote shared mailbox by using ECP into distribution group in Exchange Server 2016 hybrid environment 4547715 New created search folder retention policy is changed in Exchange Server 2016 4547722 Can’t go from Office 365 to Enterprise in Exchange Server 2016 Exchange admin center (EAC) if Chrome SameSite Cookie is enabled 4547723 Can’t sign in to Office 365 if configuring hybrid with Chrome SameSite Cookie enabled in Exchange Server 2016 4547716 Event ID 1325 and Test-ExchangeSearch crashes application pool with NullReferenceException in Exchange Server 2016 4536987 Description of the security update for Microsoft Exchange Server 2016: February 11, 2020 4540123 Description of the security update for Microsoft Exchange Server 2016: March 10, 2020

This cumulative update is a security update. It includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. Notes:If you are upgrading from Cumulative Update 2 for Exchange Server 2019 or a later cumulative update for Exchange Server 2019 to Cumulative Update 4 for Exchange Server 2019, then there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you has ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 2 for Exchange Server 2019), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. a. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD commandis run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. b. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages: To avoid the error messages, either the user should join Schema Admins and Enterprise Admins groups, or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then the Exchange admin user can start Setup. Autodiscover Event ID 1 after installing Cumulative Update 3 for Exchange Server 2019. For more information, see KB 4532190. The Export-ModernPublicFolderStatistics.ps1 script doesn’t work in Microsoft Exchange Server 2019. For more information, see KB 4536552. Issues that this cumulative update fixes This cumulative update also fixes the issues that are described in the following Microsoft Knowledge Base articles: 4528696 Exchange PowerShell cmdlets take longer time to run in Exchange Server 2019 4528695 Event ID 4009 when using SubjectOrBodyMatchesPatterns on Edge server in Exchange Server 2019 4528694 Can’t open .ics file in Outlook on the web in Exchange Server 2019 4528692 “A parameter was specified that isn’t valid” error when creating transport rule in Exchange Server 2019 4523519 Set-SendConnector doesn’t work for Exchange Server in hybrid scenarios with Edge Server installed 4528688 Only one recipient shows when saving draft by using Exchange ActiveSync version 16.0 in Exchange Server 2019 4528693 Get-CalendarDiagnosticLog is proxied for queries within the same forest in Exchange Server 2019 4528687 NotificationClient logs aren’t purged and consume lots of disk in Exchange Server 2019 4528689 Outlook on the web shows MailTip when recipients equal the large audience size in Exchange Server 2019 4528690 Can’t move or delete folder in Outlook online mode if the destination has a folder with the same name in Exchange Server 2019 4532744 System.ArgumentNullException when you use Set-user to assign block legacy auth policy in Exchange Server 2019 4532747 Address list separation not working for a user without a mailbox in Exchange Server 2019 4523171 Description of the security update for Microsoft Exchange Server 2019, 2016, and 2013: November 12, 2019

This cumulative update includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. Notes: If you are upgrading from Cumulative Update 13 for Exchange Server 2016 to Cumulative Update 14 for Exchange Server 2016, then there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you has ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 13 for Exchange Server 2016), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. a. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD command is run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. b. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages:To avoid the error messages, either the user should join Schema Admins and Enterprise Admins groups, or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then the Exchange admin user can start Setup. The Set-SendConnector cmdlet does not work for Exchange Server 2016 in hybrid scenarios that have a Edge server installed. For more information, see KB 4523519. Autodiscover Event ID 1 after installing Cumulative Update 14 for Exchange Server 2016. For more information, see KB 4532190. Issues that this cumulative update fixes This cumulative update fixes the issues that are described in the following Microsoft Knowledge Base articles: 4515255 “X-InnerException: Microsoft.Mapi.MapiExceptionRpcServerTooBusy” error when you try to use a mailbox in Exchange Server 2016 4515254 Event 1009 frequently occurs in application logs for lagged database copies in Exchange Server 2016 4502159 Adding or removing mailbox permission in EAC doesn’t address the msExchDelegateListLink attribute in Exchange Server 2016 4515276 Room mailbox accepts a meeting as “Free” if a booking delegate is set in Exchange Server 2016 4515275 Enable Get/Restore-RecoverableItems to work with Purges folder in Exchange Server 2016 4515274 AutodiscoverV2 request returns REST API endpoint not AutoDiscoverV1 endpoint in Exchange Server 2016 4515269 SentToMemberOf shows every recipient type not distribution groups when creating transport rule in Exchange Server 2016 4515272 Message is blocked in “SMTP Delivery to Mailbox” queue if exchange server is added in groups of a child domain in Exchange Server 2016 4515271 Can’t convert a migrated remote user mailbox to shared in Exchange Server 2016 4515270 SubmissionQueueLengthMonitor shows “System.ArgumentException: Transition timeout…” in Exchange Server 2016 4515267 NDR occurs when you resend message from alternate journaling mailbox to journaling mailbox in Exchange Server 2016 4515265 Removing In-Place Hold doesn’t work for mailboxes in different domains in Exchange Server 2016 4515264 FindPeople request from Skype for Business on Mac fails with “Invalid Shape Specification” in Exchange Server 2016 4515263 Hide the “Validate-MailFlowThroughFrontDoor” command for Exchange Server 2016 4515262 Enable Remove-MobileDevice to delete mobile devices after migrating to Office 365 from Exchange Server 2016 4515261 Can’t copy eDiscovery search results for mailboxes with Exchange online archives in Office 365 in Exchange Server 2016 4515273 Mailbox auditing fails when you use SHA1Managed in Exchange Server 2016 4515266 Infinite loop in Recurrence.GetNumberOfYearsBetween() with the Japanese calendar in Exchange Server 2016 4520319 S/MIME signed reply draft behaves like the first message in conversation in Exchange Server 2016 4515832 Description of the security update for Microsoft Exchange Server 2019 and 2016: September 10, 2019

This cumulative update is a security update. It includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in Setup, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to run the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated Setup has the appropriate permissions. Notes:If you are upgrading from Cumulative Update 2 for Exchange Server 2019 to Cumulative Update 3 for Exchange Server 2019, then there’s no need to run the /PrepareAD or /PrepareDomain. No additional actions (prepareAD, prepareDomain, or assigning permissions) are required. If you has ever skipped a Cumulative Update (for example, you are upgrading from an earlier version before Cumulative Update 2 for Exchange Server 2019), or this is a first Exchange Server installation in the AD, then this Known Issue section should be taken care of. a. About the /PrepareDomain operation in multidomain: The /PrepareDomain operation automatically runs in the Active Directory domain in which the /PrepareAD commandis run. However, it may be unable to update other domains in the forest. Therefore, a domain administrator should run the /PrepareDomain in other domains in the forest. b. About the permission question: As the /PrepareAD is triggered in Setup, if the user who initiates Setup isn’t a member of Schema Admins and Enterprise Admins, the readiness check will fail and you receive the following error messages: To avoid the error messages, either the user should join Schema Admins and Enterprise Admins groups, or another user in Schema Admins and Enterprise Admins groups manually runs the /PrepareAD for this Cumulative Update first. Then the Exchange admin user can start Setup. The Set-SendConnector cmdlet does not work for Exchange Server 2019 in hybrid scenarios that have a Edge server installed. For more information, see KB 4523519. Autodiscover Event ID 1 after installing Cumulative Update 3 for Exchange Server 2019. For more information, see KB 4532190. Issues that this cumulative update fixes This cumulative update also fixes the issues that are described in the following Microsoft Knowledge Base articles: 4515257 Hash mismatch is reported for Exchange DLLs in the bin directory of Exchange Server 2019 4513500 Can’t sign in to OWA or EAC after you install Exchange Server 2019 CU2 with AD FS 4502159 Adding or removing mailbox permission in EAC doesn’t address the msExchDelegateListLink attribute in Exchange Server 2019 and 2016 4515276 Room mailbox accepts a meeting as “Free” if a booking delegate is set in Exchange Server 2019 and 2016 4515275 Enable Get/Restore-RecoverableItems to work with Purges folder in Exchange Server 2019 and 2016 4515274 AutodiscoverV2 request returns REST API endpoint not AutoDiscoverV1 endpoint in Exchange Server 2019 and 2016 4515269 SentToMemberOf shows every recipient type not distribution groups when you create transport rule in Exchange Server 2019 and 2016 4515272 Message is blocked in “SMTP Delivery to Mailbox” queue if exchange server is added in groups of a child domain in Exchange Server 2019 and 2016 4515271 Can’t convert a migrated remote user mailbox to shared in Exchange Server 2019 and 2016 4515270 SubmissionQueueLengthMonitor shows “System.ArgumentException: Transition timeout…” in Exchange Server 2019 and 2016 4515267 NDR occurs when you resend message from alternate journaling mailbox to journaling mailbox in Exchange Server 2019 and 2016 4515265 Removing In-Place Hold doesn’t work for mailboxes in different domains in Exchange Server 2019 and 2016 4515264 FindPeople request from Skype for Business on Mac fails with “Invalid Shape Specification” in Exchange Server 2019 and 2016 4515263 Hide the “Validate-MailFlowThroughFrontDoor” command for Exchange Server 2019 and 2016 4515262 Enable Remove-MobileDevice to delete mobile devices after migrating to Office 365 from Exchange Server 2019 and 2016 4515261 Can’t copy eDiscovery search results for mailboxes with Exchange online archives in Office 365 in Exchange Server 2019 and 2016 4515273 Mailbox auditing fails when using SHA1Managed in Exchange Server 2019 and 2016 4515266 Infinite loop in Recurrence.GetNumberOfYearsBetween() with the Japanese calendar in Exchange Server 2019 and 2016 4520319 S/MIME signed reply draft behaves like the first message in conversation in Exchange Server 2019 and 2016 4515832 Description of the security update for Microsoft Exchange Server 2019 and 2016: September 10, 2019

This cumulative update includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. Known issues The Set-SendConnector cmdlet does not work for Exchange Server 2013 in hybrid scenarios that have a Edge server installed. For more information, see KB 4523519. Issues that this cumulative update fixes This cumulative update fixes the issues that are described in the following Microsoft Knowledge Base articles: 4502131 “TLS negotiation failed with error UnknownCredentials” error after updating TLSCertificateName on Office 365 send connector in Exchange Server 2013 hybrid environment 4503028 Description of the security update for Microsoft Exchange Server 2013 and 2010: June 11, 2019

This cumulative update is a security update. It includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. Issues that this cumulative update fixes 4502134 Can’t get all the emails when searching mailbox by using an end date that’s different from today in Exchange Server 2019 4502135 Correct the error message that you receive when installing Exchange Server 2019 in an organization that has Exchange Server 2010 installed 4502154 Providing information to administrators when auto forward limit is reached in Exchange Server 2019 and 2016 4502155 “The primary SMTP address must be specified when referencing a mailbox” error when you use impersonation in Exchange Server 2019 and 2016 4502156 Audit logs aren’t updated when “-WhatIf” is used as $false in the command in Exchange Server 2019 and 2016 4502157 The Find command not returning the HasAttachments element in Exchange Server 2019 and 2016 4502158 SyncFolderItems contains duplicated ReadFlagChange items in Exchange Server 2019 and 2016 4502131 “TLS negotiation failed with error UnknownCredentials” error after you update TLSCertificateName on Office 365 send connector in Exchange Server 2019 hybrid environment 4502132 Can’t reply to old emails after migration even though old legacyExchangeDN is set to migrated mailbox in Exchange Server 2019 and 2016 4502136 The response of FETCH (BODYSTRUCTURE) command of IMAP violates RFC 3501 in Exchange Server 2019 and 2016 4502140 Can’t preview an eDiscovery search when there are multiple domains in Exchange Server 2019 and 2016 4502141 Appointment that’s created by responding to an email message doesn’t show in any Outlook calendar views in Exchange Server 2019 and Exchange Server 2016 4502133 Can’t use Outlook on the web to reply a partner email through mutual TLS in Exchange Server 2019 and 2016 4488396 Can’t search any results in manually added shared mailbox in Outlook in Exchange Server 2019 and 2016 4488078 Public folder contact lists don’t show contact’s profile picture in Outlook on the web in Exchange Server 2019 and 2016 4499503 Heavy organizational forms traffic because of materialized restriction when organization forms library has more than 500 items in Exchange Server 2019 and 2016 4503027 Description of the security update for Microsoft Exchange Server 2019 and 2016: June 11, 2019

This cumulative update includes fixes for nonsecurity issues and all previously released fixes for security and nonsecurity issues. Known issues in this cumulative update In multidomain Active Directory forests in which Exchange is installed or has been prepared previously by using the /PrepareDomain option in SETUP, this action must be completed after the /PrepareAD command for this cumulative update has been completed and the changes are replicated to all domains. Setup will try to execute the /PrepareAD command during the first server installation. Installation will finish only if the user who initiated SETUP has the appropriate permissions. The Set-SendConnector cmdlet does not work for Exchange Server 2016 in hybrid scenarios that have a Edge server installed. For more information, see KB 4523519. Issues that this cumulative update fixes This cumulative update fixes the issues that are described in the following Microsoft Knowledge Base articles: 4502154 Providing information to administrators when auto forward limit is reached in Exchange Server 2016 4502155 “The primary SMTP address must be specified when referencing a mailbox” error when using impersonation in Exchange Server 2016 4502156 Audit logs aren’t updated when “-WhatIf” is used as $false in the command in Exchange Server 2016 4502157 The Find command not returning the HasAttachments element in Exchange Server 2016 4502158 SyncFolderItems contains duplicated ReadFlagChange items in Exchange Server 2016 4502131 “TLS negotiation failed with error UnknownCredentials” error after updating TLSCertificateName on Office 365 send connector in Exchange Server 2016 hybrid environment 4502132 Can’t reply to old emails after migration even though old legacyExchangeDN is set to migrated mailbox in Exchange Server 2016 4502136 The response of FETCH (BODYSTRUCTURE) command of IMAP violates RFC 3501 in Exchange Server 2016 4502140 Can’t preview an eDiscovery search when there are multiple domains in Exchange Server 2016 4502141 Appointment that’s created by responding to an email message doesn’t show in any of Outlook calendar views in Exchange Server 2016 4502133 Can’t use Outlook on the web to reply a partner email through mutual TLS in Exchange Server 2016 4488396 Can’t search any results in manually added shared mailbox in Outlook in Exchange Server 2016 4488078 Public folder contact lists don’t show contact’s profile picture in Outlook on the web in Exchange Server 2016 4499503 Heavy organizational forms traffic due to materialized restriction when organization forms library has more than 500 items in Exchange Server 2016 4503027 Description of the security update for Microsoft Exchange Server 2019 and 2016: June 11, 2019

One of the improvements in Exchange 2019 is that that the client configuration became more easier. This is caused because of several improvements in Autodiscover. The clients that connect via EWS usually are connected to the EWS Endpoint using Autodiscover. It is known that Autodiscover provides also information for other protocol connections also and it support also multiforest configurations. When Exchange server is installed a virtual directory called Autodiscover is created. After the appropriate URL are configured and stored in Active Directory the Client Access services that run on the Mailbox server provide authentication services and proxy services for both internal and external client connection.That results that Outlook clients can then connect to Exchange using only the user name and password. Autodiscover and Active Directory As said previously the creation of the Autodiscover virtual directory allows Outlook to automatically discover the necessary Exchange mailbox settings saving the users from having to write down and remember server names, ports, protocols, databases, etc. The user can simply provide a username and password and the rest is carried by Outlook. During the virtual directory creation an SCP object is also created in Active Directory. That SCP object stores the authoritative URLs for the Autodiscover service and provides them to domain-joined computers. The SCP object points to the Exchange server and provides additional Autodiscover information to clients trying to connect to Exchange. The SCP object locates the Autodiscover server or endpoint that’s appropriate for the user trying to connect. It provides an easy way for domain-joined mail clients to look up Autodiscover servers. There are two types of SCP objects for the Autodiscover service that Exchange publishes. SCP pointers and SCP URLs. SCP pointers contain information that points to specific LDAP servers that are then used to locate Autodiscover SCP objects in the user’s Active Directory domain. SCP URLs contain Autodiscover URLs for Autodiscover endpoints. The Autodiscover service URL will be either of the values below: https://yourdomain/autodiscover/autodiscover.xml https://autodiscover.yourdomain/autodiscover/autodiscover.xml The URL used will depend on whether the Autodiscover service is configured on a separate site or not. Autodiscover in DNS Exchange Server 2019 reduces the number of required namespaces since it does not require RPC Client Access namespaces. The Client Access services now proxy connection requests to whatever Mailbox server is hosting the active Mailbox database for the mailbox being connected to. A new feature in Exchange 2019 is the ability of a a Mailbox server to proxy a session to another mailbox server in a different Active Directory site thus eliminating the need for failback namespaces in DAG activation situations. Outlook and Autodiscover If Autodiscover is properly configured, Outlook clients can authenticate to Active Directory with just a user’s credentials. It will automatically search for the Autodiscover SCP objects for the domain. Once it finds the Autodiscover service, the Outlook client will connect to the Client Access services on the first Mailbox server it finds. Outlook will then collect profile information in XML format. This information is required to connect to the mailbox. Autodiscover can use one of four methods to configure an Outlook client: Connect to https://yourdomain/AutoDiscover/AutoDiscover.xml Connect to: https://autodiscover.yourdomain/AutoDiscover/AutoDiscover.xml Autodiscover redirect URL: http://autodiscover.yourdomain/autodiscover/autodiscover.xml Search for DNS SRV record The first two methods above are typical for smaller organizations with a single SMTP namespace. The second two are typical in multiple-SMTP namespace scenarios. Outlook uses the Autodiscover service to locate a new connection point. Autodiscover returns the following information to the Outlook client: User display name Internal and external connection settings Mailbox server hosting the active copy of the user’s mailbox URLs for various Outlook features (OAB, OWA, etc.) Outlook Anywhere server settings If the Exchange information for a user changes, the Outlook client will use the Autodiscover service to automatically reconfigure the user’s profile. This commonly occurs when a mailbox is moved. When this happens, Outlook contacts the Autodiscover service and automatically updates the user’s profile with the new mailbox location so that it can connect. Autodiscover and certificates When Exchange is installed, the installation process creates a self-signed certificate that’s signed by the Exchange server itself. This certificate is automatically installed on the server. However it is recommended that you use public certificate from a trusted third party. You can use the Microsoft Remote Connectivity Analyzer tool to confirm that the Autodiscover service in Exchange 2019 is accessible and functioning as expected. To test Autodiscover with the tool, launch the tool and select the Outlook Connectivity test. The tool will then attempt to connect to Exchange, using Autodiscover. If it fails, there is likely an issue with the external URLs configured in Exchange. Reading the results provided by the tool should reveal clues regarding why connectivity failed.

Hello to all!! Today Exchange Product Group announced a long-expected addition on Office 365. The ability to migrate G-Suite calendars and contacts to Office 365 with nothing more than Office 365 native tools. Currently there is a 2GB migration limit per day. This is a great step forward but there are many more things to come. Migration currently does not support Mail: Vacation Settings or Automatic reply settings as well as Filters or Rules Meeting Rooms: Room bookings Calendar: Shared calendars, cloud attachments, Google Hangout links and event colors Contacts: A maximum of three email addresses per contact are migrated over Contacts: Gmail tags, contact URLs and custom tags are not migrated over You can read more information here Happy Migrations!!!

Today Exchange Team announced the new and updated site for the Exchange Deployment Assistant – https://assistants.microsoft.com! . This is a expected move since all the assistants are moved under assistants.microsoft.com site, following the Microsoft move to docs.microsoft.com . The new assistant focus solely on on-premises deployments. For online and hybrid scenarios, there are two different resources offering guidance: the EDA, and the Office 365 mail migration advisors. When you go to the new site, you’ll see two options: The first option, On-premises Exchange deployments, will go to the Deployment Assistant and all the on-premises deployment options we all know and love today with Exchange 2019 scenarios coming soon! The second option, Migrate Exchange to Office 365 will lead you to the Office 365 mail migration advisors. The Office 365 mail migration advisors offer the best solutions for helping you migrate your organization to Office 365 including staged and cut-over migrations and all flavors of hybrid migrations. The existing Deployment Assistant will remain available until the end of April 2019. Happy advising!!!!

Today Exchange Team announce the quarterly servicing updates, cumulative and update rollups, for all supported versions of Exchange Server. There are some important changes. What changes in Exchange Web Services Push Notifications The update to EWS Push Notifications is considered a critical security update and customers should deploy the update as soon as they understand and accept any potential impact. The change in Push Notification authentication is a permanent change to the product and necessary to protect the security of an Exchange Server. As outlined in KB4490060 the fundamental change is the authentication between EWS clients and Exchange server. This only affects Push notificationsan and leaves Pull and Streaming Notifications unaffected and its applicable to all EWS clients. Also a computer reset of Exchange server credentials is required in Active Directory as a best practice. Decreasing Exchange Rights in the Active Directory The Team has also made a change in the Active Directory rights granted to Exchange Servers reducing the items that exchange is able to write security descriptors as outlined in KB4490059. Removing Legacy Auth protocols from Exchange Servers In Exchange Server 2019 Cumulative Update 1, there is a new cmdlet that restrict legacy authentication protocols on a per protocol and user by user basis. This change came from Office365 which already has the same functionality implemented. Downloads The KB articles are the following: Exchange Server 2019 Cumulative Update 1 (KB4471391) Exchange Server 2016 Cumulative Update 12 (KB4471392) Exchange Server 2013 Cumulative Update 22 (KB4345836) Exchange Server 2010 Service Pack 3 Update Rollup 26 (KB4487052) Happy Patching!!!!