Gemini said
Since this issue is user-specific (travels with the user to different machines) but client-specific (works in OWA but not Outlook Desktop), you are dealing with a breakdown in how the Outlook Desktop client authenticates or retrieves the "App List" from the Exchange server.
Given that you've already tried new profiles and basic cache clearing, here are all the possible ways to resolve this, categorized by the level of intervention required.
1. The Identity & UPN Mismatch Fixes
Since a UPN change occurred, Outlook Desktop may be confused about which identity to use for its internal "Web Hub."
Reset the Office Global Identity: Even if you signed out, the registry holds onto the old identity.
Navigate to: HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity\Identities.
__**Delete**__ the subkeys here. This forces the Office "Identity Manager" to create a fresh token based on the current UPN/SMTP.
__**Check the `mail` Attribute:**__ Outlook Desktop often relies on the `mail` attribute in Active Directory to map add-ins. Ensure the `mail` attribute matches the new Primary SMTP/UPN exactly. If OWA works, the server knows the user, but the client-side "discovery" might be failing due to this mismatch.
2. Deep Mailbox Configuration (MFCMAPI)
Add-in visibility in Outlook Desktop is controlled by a hidden "dictionary" in the mailbox. If this object is corrupted, OWA (which builds the list on the fly) will work, but Desktop (which caches the list) will not.
Reset the Extension Master List:
Open MFCMAPI > Session > Logon.
Open the Mailbox Store > __**Root Container**__ > __**Top of Information Store**__.
Right-click __**Inbox**__ > __**Open Associated Contents Table**__.
Look for an item with Message Class: `IPM.Configuration.ExtensionMasterList`.
__**Delete it.**__ (Outlook will regenerate it on the next restart).
__**Clear the OWA User Options:**__
Also in the Associated Contents Table, look for `IPM.Configuration.OWA.UserOptions`. Deleting this resets the web-side settings that Outlook Desktop sometimes "checks" during the add-in handshake.
3. Connectivity & Endpoint Validation
Outlook Desktop uses Exchange Web Services (EWS) to load add-ins. OWA does not.
Validate EWS for the User: Run this in Exchange Management Shell:
Get-CASMailbox -Identity <user> | Select EwsEnabled, EwsAllowOutlook.
If `EwsAllowOutlook` is `$false`, add-ins will fail in Desktop but work in OWA.
__**Test the EWS Metadata URL:**__ From an affected machine, logged in as the affected user, try to browse to:
`https://<YourExchangeServer>/ews/exchange.asmx`.
If you get an auth prompt or a certificate error, the WebView2 control inside Outlook is likely failing to authenticate silently.
4. Client-Side "Web Extensions" Reset
You mentioned clearing app data, but specifically, the WEF (Web Extension Framework) cache is the most common culprit for the 64-bit Office 365 app.
The "Nuclear" WEF Clear:
Close Outlook.
Delete the contents of: `%LocalAppData%\Microsoft\Office\16.0\Wef\`
Delete the contents of: `%LocalAppData%\Microsoft\Office\16.0\Wef\WebView2` (if present).
Restart Outlook and wait 5–10 minutes for the background sync to complete.
5. Privacy & Connected Experiences
Microsoft has tied Add-ins to "Optional Connected Experiences."
Go to File > Office Account > Account Privacy > Manage Settings.
Ensure "Enable optional connected experiences" is checked. If this is off, the "Get Add-ins" store and all Exchange-side web add-ins are instantly disabled in the desktop client.
6. Registry "Hard Resets"
If the UPN change left "ghost" accounts in the Office activation layer:
- Disable ADAL/WAM (Temporary Test): * Add
DisableADALatopWAMOverride = 1 (DWORD) under HKCU\Software\Microsoft\Office\16.0\Common\Identity.
- This forces Outlook to use the older, more stable authentication method for Exchange 2016. If add-ins reappear, your issue is a Modern Auth / Token mismatch caused by the UPN change.
Gemini said
Since this issue is user-specific (travels with the user to different machines) but client-specific (works in OWA but not Outlook Desktop), you are dealing with a breakdown in how the Outlook Desktop client authenticates or retrieves the "App List" from the Exchange server. Given that you've already tried new profiles and basic cache clearing, here are all the possible ways to resolve this, categorized by the level of intervention required.1. The Identity & UPN Mismatch Fixes
Since a UPN change occurred, Outlook Desktop may be confused about which identity to use for its internal "Web Hub."
- Reset the Office Global Identity: Even if you signed out, the registry holds onto the old identity.
- Navigate to:
HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity\Identities.
- Delete the subkeys here. This forces the Office "Identity Manager" to create a fresh token based on the current UPN/SMTP.
- Check the
mail Attribute: Outlook Desktop often relies on the mail attribute in Active Directory to map add-ins. Ensure the mail attribute matches the new Primary SMTP/UPN exactly. If OWA works, the server knows the user, but the client-side "discovery" might be failing due to this mismatch.
2. Deep Mailbox Configuration (MFCMAPI)
Add-in visibility in Outlook Desktop is controlled by a hidden "dictionary" in the mailbox. If this object is corrupted, OWA (which builds the list on the fly) will work, but Desktop (which caches the list) will not.
- Reset the Extension Master List:
- Open MFCMAPI > Session > Logon.
- Open the Mailbox Store > Root Container > Top of Information Store.
- Right-click Inbox > Open Associated Contents Table.
- Look for an item with Message Class:
IPM.Configuration.ExtensionMasterList.
- Delete it. (Outlook will regenerate it on the next restart).
- Clear the OWA User Options:
- Also in the Associated Contents Table, look for
IPM.Configuration.OWA.UserOptions. Deleting this resets the web-side settings that Outlook Desktop sometimes "checks" during the add-in handshake.
3. Connectivity & Endpoint Validation
Outlook Desktop uses Exchange Web Services (EWS) to load add-ins. OWA does not.
- Validate EWS for the User: Run this in Exchange Management Shell:
-
Get-CASMailbox -Identity <user> | Select EwsEnabled, EwsAllowOutlook.
- If
EwsAllowOutlook is $false, add-ins will fail in Desktop but work in OWA.
- Test the EWS Metadata URL: From an affected machine, logged in as the affected user, try to browse to:
-
https://<YourExchangeServer>/ews/exchange.asmx.
- If you get an auth prompt or a certificate error, the WebView2 control inside Outlook is likely failing to authenticate silently.
4. Client-Side "Web Extensions" Reset
You mentioned clearing app data, but specifically, the WEF (Web Extension Framework) cache is the most common culprit for the 64-bit Office 365 app.
- The "Nuclear" WEF Clear:
- Close Outlook.
- Delete the contents of:
%LocalAppData%\Microsoft\Office\16.0\Wef\
- Delete the contents of:
%LocalAppData%\Microsoft\Office\16.0\Wef\WebView2 (if present).
- Restart Outlook and wait 5–10 minutes for the background sync to complete.
5. Privacy & Connected Experiences
Microsoft has tied Add-ins to "Optional Connected Experiences."
- Go to File > Office Account > Account Privacy > Manage Settings.
- Ensure "Enable optional connected experiences" is checked. If this is off, the "Get Add-ins" store and all Exchange-side web add-ins are instantly disabled in the desktop client.
6. Registry "Hard Resets"
If the UPN change left "ghost" accounts in the Office activation layer:
- Disable ADAL/WAM (Temporary Test): * Add
DisableADALatopWAMOverride = 1 (DWORD) under HKCU\Software\Microsoft\Office\16.0\Common\Identity.
- This forces Outlook to use the older, more stable authentication method for Exchange 2016. If add-ins reappear, your issue is a Modern Auth / Token mismatch caused by the UPN change.