To narrow down this issue, I would like to first ask the following questions:
1.Does this issue happen to all users or just some of them?
2.Are the affected devices domain-joined or external?
Please run the following command in Exchange Management Shell to get the server which hosts the OAB generation mailbox:
Get-Mailbox -Arbitration | where {$_.PersistedCapabilities -like "*OAB*"} | Format-List Name,ServerName
Then check this path %ExchangeInstallPath%ClientAccess\OAB\<OAB GUID> on the server to see if the OAB folder exists.
If the folder doesn't exist, run the following command in EMS to force the OAB to update:
Get-OfflineAddressBook | Update-OfflineAddressBook
Once the folder is created, please retry OAB download in Outlook.
If the issue persists, please run a Test E-mail Autoconfiguration in Outlook and check the result under Results tag for OAB url.
And run the following command and post the OAB settings:
(Don't forget to hide your personal information in your post)
Get-OfflineAddressBook | fl Name,GlobalWebDistributionEnabled,VirtualDirectories
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