Windward System Five & Microsoft Outlook 32bit Edition.

See https://support.windwardsoftware.com/a/solutions/articles/66000482535

Starting release version 6.2.4.168, System Five will no longer work on a 64bit edition of Outlook. System Five is a 32bit application and for this integration to work properly Outlook needs to be on the same platform.

When installing Outlook 32bit, you must have administrator access to ensure that Windows Registry and Windows File Systems are propagated properly.

However, this is not required when running or using the software.

The Error

The Solution
Uninstall MS Outlook 64bit and install a 32bit edition.

If after doing so, and you still get the same error. This means that System Five is still detecting the 64bit and not seeing and newly installed 32bit.

A possible workaround is to manually set the 32bit key inside the Windows Registry HKEY_LOCAL_MACHINE\software\Wow6432Node\microsoft\office\16\Outlook\Bitness

Run ‘Regedit
Navigate to the location as shown above.
If you do not see a value under “Bitness” or you are seeing “x64’, double-click it and type in ‘x86’ to tell it that is a 32bit edition.
Exit the Windows Registry window and try again.