Yes it's annoying isn't it, would be better if there was a regular setting menu option for it but this is all we've got for now. Any settings that Microsoft intend to be set centrally by mass administration (e.g. by the IT department in a large college deployment) are most commonly set by group policy and so far we've just had this variation exposed as a raw registry value. While I'm also in a centrally administered environment and setting this registry value worked for me, your own IT department will certainly be the best port of call for which configurations are applied to your device and what they best way of achieving this for you is.
Hopefully adding the value to the additional /outlook/ locaiton is the missing link but if it still doesn't want to apply when you reload Outlook perhaps it's worth checking you've got a version of Outlook that knows about this latest registry value and any policy that IT are applying that might override this setting/cause it not to apply. Usually if your device is tightly administered you won't be able to edit the registry in the first place, but again your IT department should be able to direct you to the right place to report this and work through with if it doesn't work straight away.