The update was failing on step 5 - mailbox role.
The error log contained:
Error:The following error was generated when "$error.Clear(); if (($RoleIsDatacenter -ne $true) -and ($RoleIsDatacenterDedicated -ne $true)) { if (test-ExchangeServersWriteAccess -DomainController $RoleDomainController -ErrorAction SilentlyContinue) { # upgrade the discovery mailboxes to R5 version, this will fix the RecipientDisplayType property of the discovery mailbox which was wrong in R4. get-mailbox -RecipientTypeDetails DiscoveryMailbox -DomainController $RoleDomainController | where {$_.IsValid -eq $false} | set-mailbox -DomainController $RoleDomainController $name = [Microsoft.Exchange.Management.RecipientTasks.EnableMailbox]::DiscoveryMailboxUniqueName; $dispname = [Microsoft.Exchange.Management.RecipientTasks.EnableMailbox]::DiscoveryMailboxDisplayName; $mbxs = @( get-mailbox -Filter {name -eq $name} -IgnoreDefaultScope -resultSize 1 ); if ( $mbxs.length -eq 0) { $dbs = @(get-MailboxDatabase -Server:$RoleFqdnOrName -DomainController $RoleDomainController); if($dbs.Length -ne 0) { $mbxUser = @(get-user -Filter {name -eq $name} -IgnoreDefaultScope -ResultSize 1); if ($mbxUser.Length -ne 0) { enable-mailbox -Discovery -identity $mbxUser[0] -DisplayName $dispname -database $dbs[0].Identity; } } } } else { write-exchangesetuplog -info "Skipping creating Discovery Search Mailbox because of insufficient permission." } } " was run: "Microsoft.Exchange.Data.DataValidationException: Database is mandatory on UserMailbox.".
What you are looking for is highlighted in bold.
A simple Exchange Powershell command would reveal the real culprit: Get-Mailbox
I got a list of all user mailbox, however, at the very top, there was an error saying that the Discovery Mailbox is corrupt.
To fix this I followed this Microsoft KB:
1. Run the following command to delete the default discovery mailbox
2. In the message asking you to confirm that you want to delete the mailbox and the corresponding Active Directory user object, type Y, and then press Enter.Remove-Mailbox "DiscoverySearchMailbox{D919BA05-46A6-415f-80AD-7E09334BB852}"
2.1 In my case, I had to restart the Exchange server, because it would not let me re-create the discovery mailbox, so keep that in mind.
A new user object is created in Active Directory when you create the discovery mailbox in the next step.
3. Run the following command to re-create the default discovery mailbox.
New-Mailbox -Name "DiscoverySearchMailbox{D919BA05-46A6-415f-80AD-7E09334BB852}" -Alias "DiscoverySearchMailbox{D919BA05-46A6-415f-80AD-7E09334BB852}" -DisplayName "Discovery Search Mailbox" -Discovery4. Run the following command to assign the Discovery Management role group permissions to open the default discovery mailbox and view search results.
Add-MailboxPermission "DiscoverySearchMailbox{D919BA05-46A6-415f-80AD-7E09334BB852}" -User "Discovery Management" -AccessRights FullAccess -InheritanceType all
Once this is done, you can restart you CU and it should work.
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