Archive settings in Microsoft Outlook 2016, do not migrate any mail located in subfolders

Question

So, I've been experimenting with a few computers, and various settings, but the long and short is that Outlook 2016 seems to simply ignore all subfolders when archiving.

Here are my steps:

MailBox Layout:

Inbox
-- Subfolder 1
-- Message 1
-- Message 2
-- -- Subfolder 2
-- -- Message 3
-- -- Message 4

I go to File > Info > Tools > Clean up old items and select Archive this folder and all subfolders.

From here, I choose Subfolder 1, my date range (which I confirm includes email in Subfolder 1 and 2), my archive location, and click OK.

When my archive is complete, it resembles this:

Archive Layout:

Inbox
-- Subfolder 1
-- Message 1
-- Message 2
-- -- Subfolder 2
-- -- 
-- -- 

The Subfolder 2 is created, but no messages are migrated.

Any idea how I can archive subfolders in Outlook 2016?

*Note, I have also tested this with the AutoArchiving settings, with the exact same result.