We have had a few cases where an older version of Outlook was updated to Outlook 2019 or later to accommodate modern authentication. It would work for a while then the user would begin getting repeatedly prompted for their password because it stopped using modern authentication.

For some reason, the following registry entries were either missing or changed. Changing/adding them resolved the issue:

HKCU\SOFTWARE\Microsoft\Office\xx\Common\Identity\EnableADAL
REG_DWORD    1

HKCU\SOFTWARE\Microsoft\Office\xx\Common\Identity\Version
REG_DWORD    1

HKCU\SOFTWARE\Microsoft\Office\xx\Common\Identity\DisableADALatopWAMOverride
REG_DWORD    1

HKCU\SOFTWARE\Microsoft\Office\xx\Common\Identity\DisableAADWAM
REG_DWORD    1

HKCU\Software\Microsoft\Exchange\AlwaysUseMSOAuthForAutoDiscover
REG_DWORD    1

Later versions of Outlook do not have the ability to create a profile without a working email address. Such profiles are commonly used when Outlook is being used only to open PST files that have been created as archives.

Running this command will create such a profile:

Outlook.exe /PIM <profile name>

So, to create a new profile called “snapshot”:

Outlook.exe /PIM snapshot

Remember that Outlook’s search index will have to be built for the data file(s) associated with this new profile so the search function will be limited at first.

The shortcuts located at the bottom of the folder list in Outlook 365 (Mail, Calendar, People, Notes, etc.,) moves to a narrow vertical bar on the left with some of the shortcuts, such as Notes and Folders, missing.

For now, the only fix I have found is a registry entry:

HKCU\Software\Microsoft\Office\16.0\Common\ExperimentEcs\Overrides

Add/change 32-bit Dword:

Microsoft.Office.Outlook.Hub.HubBarcollapsible = 0

Workgroup printers stop working after Windows Update for RPC exploit (KB5005565.) Attempts to reconnect give error 0x0000011b

This can be resolved by adding/changing this registry entry:

HKLM\System\CurrentControlSet\Control\Print

Add DWORD RpcAuthnLevelPrivacyEnabled = 0

Then restart the Print Spooler service

This known issue was corrected by Microsoft on 2/24/2022.

1. Close Outlook
2. In REGEDIT, browse to HKCU\Software\Microsoft\Office\16.0\Outlook\Profiles
3. Locate the Outlook Profile name of the profile that the shared mailbox is not updating and select it.
4. In Registry Editor choose Edit, Find, and search for registry key name:  0102663e
5. Locate this key in the profile where the parent key is just above the GroupStore as shown below:
   
6. Right click on key name: 0102663e and select Delete.
7. Close Registry Editor and restart Outlook.

It will take a minute or so for the sync to re-establish.

Later versions of Outlook 365 have an “abbreviated” version of the Permissions tab on its folders (like Calendar) that just shows “Custom” without any detail. To restore the proper useful detail in versions 1903 and later:

HKCU\Software\Microsoft\Office\16.0\Outlook\Options\Calendar\
DWORD: ShowLegacySharingUX
Value: 1

When updating a Windows 7/8 machine to Windows 10, it may fail with a message box that says “Windows (10 or 11) has failed” with only an OK button. Here’s how to resolve this:

1. Create an ISO with the Media Creation Tool.
2. Extract the ISO into a folder (WinRAR will do this.)
3. Right-click on Setup, Run as Administrator
4. On the Install Windows 10 page, click on “Change on how Windows Setup downloads updates” link and select “Not Right Now”
5. Proceed with the upgrade and it should complete successfully.

To permanently block Windows 10 from “automatically” (forcing you to) upgrade to Windows 11:

In Windows 10 Pro:

1. GPEDIT
   Local Computer Policy > Computer Configuration > Administrative Templates > Windows Components > Windows Update > Windows Update for Business

2. Edit ‘Select the target Feature Update version’ policy to ‘Enabled’ in the right of the Windows Update for Business folder to edit.
3. Set ‘Which Windows product version would you like to receive feature updates for?’ to WIndows 10
4. Set ‘Target version of Feature updates’ to 21H1 or 21H2 or 22H2 (latest)

In Windows 10 Home: (this REG file can also be used to do the following)

1. REGEDIT
   HKEY_LOCAL_MACHINE\SOFTWARE\Policies\Microsoft\Windows
2. Add key WindowsUpdate
3. Add new DWORD 32-bit named TargetReleaseVersion and set value to 1
4. Add new String Value named ProductVersion and set value to Windows 10
5. Add new String Value named TargetReleaseVersionInfo and set value to 21H2

This can happen on Windows 7 when TLS hasn’t been updated.

1. Make sure KB3140245 has been installed:
   https://www.catalog.update.microsoft.com/search.aspx?q=kb3140245
   
2. Update the registry:
   https://download.microsoft.com/download/0/6/5/0658B1A7-6D2E-474F-BC2C-D69E5B9E9A68/MicrosoftEasyFix51044.msi

(From: https://support.microsoft.com/en-us/topic/update-to-enable-tls-1-1-and-tls-1-2-as-default-secure-protocols-in-winhttp-in-windows-c4bd73d2-31d7-761e-0178-11268bb10392)

During the out-of-the-box setup procedure, stop at the screen where it asks to you select a network and:

1. Press Shift + F10
2. At the cmd window type taskmgr and then enter
3. Expand to more details
4. Find ‘Network Connection Flow’ – right click and choose End task
5. Now go back to Setup and continue to add local account

Here’s a YouTube video that shows this being done:

https://www.youtube.com/watch?v=i3NPilpkC8M