While it’s not a fantastic idea from anyone’s point of you to be using software over 10 years old that’s supported by Microsoft and really shouldn’t be used in organizations anymore, however this is why the Microsoft articles make no sense as its not supported.
Then when you continue you get this, to which regardless of what you enter it will not be accepted:
I also understand that there are many things that require legacy applications in order to work and upgraded to the latest version of office, for example, can put gremlins in the works, and nobody really wants to feed a Mogwai after midnight.
Therefore this guide outlines how to enable modern authentication in Outlook 2013, before modern authentication came along everyone was using user names and passwords in the basic digest, this is a bad idea because it does not support MFA and it’s not really informative to the user as to why they can’t login.
if you were trying to use Outlook 2013, with Office 365 and more specifically Exchange online, when you try to connect a mailbox and you will notice that you will be prompted for the username and password that will never be accepted - even if you get the username and password correct, it will continue to prompt for authentication, this is more than authentication denying you access.
The other clue I noticed was when you add a mailbox do you get the password field, if outlook 2013 is configured correctly, you should not get the password field as below :
Then when you continue you get this, to which regardless of what you enter it will not be accepted:
Hotfixes Required
In order to fix this particular problem do you need to first install the following hotfixes in the order they are as below, the ones with reboot in the column require reboots.
| 1 | KB4475607 | Download x32 | Download x64 | |
| 2 | KB3172545 | Download x32 | Download x64 | |
| 3 | KB3085565 | Download x32 | Download x64 | |
| 4 | KB4484096 | Download x32 | Download x64 | Reboot |
| 5 | KB4484156 | Download x32 | Download x64 | Reboot |
| 6 | KB4022226 | Download x32 | Download x64 | Reboot |
NOTE ; If you would like the hotfixes for the x32 version all in a ZIP file along with the registry key you can use this download link
Once you had a hotfixes installed, do you know need to enable modern authentication via either the Registry or PowerShell - both the options are outlined below:
Option 1 : Registry keys
Windows Registry Editor Version 5.00
[HKEY_CURRENT_USER\Software\Microsoft\Exchange]
"AlwaysUseMSOAuthForAutoDiscover"=dword:00000001
[HKEY_CURRENT_USER\Software\Microsoft\Office\15.0\Common]
[HKEY_CURRENT_USER\Software\Microsoft\Office\15.0\Common\Identity]
"EnableADAL"=dword:00000001
"Version"=dword:00000001
Option 2 : Powershell
# The two entries below enable modern authentication in Outlook 2013
Set-ItemProperty -Path HKCU:\\Software\\Microsoft\\Office\\15.0\\Common\\Identity -Name EnableADAL -Value 1 -Force
Set-ItemProperty -Path HKCU:\\Software\\Microsoft\\Office\\15.0\\Common\\Identity -Name Version -Value 1 -Force
# Create the HKCU:\\Software\\Microsoft\\Exchange\\AlwaysUseMSOAuthForAutoDiscover registry entry.
# This value forces Outlook to always use modern authentication.
New-Item -Path HKCU:\\Software\\Microsoft -Name 'Exchange' -Force
New-ItemProperty -Path HKCU:\\Software\\Microsoft\\Exchange -Name 'AlwaysUseMSOAuthForAutoDiscover' -Value 1 -PropertyType DWORD -Force
Check, modern authentication is enabled
if you have done this correctly, next time you start Outlook and you try to add a mailbox if you will notice that you will only get the email address option, and that you will be presented with modern authentication dialogue screen as shown below after entering your e-mail address:
