From the OW site -
"You are allowed to take two stopovers in total within your continent of origin in order to get to or from a gateway to commence or return from your international travel."
Depending on how you choose to read it, this wording would imply that continent-of-origin segments must be getting you to/from your international gateway and thus you can't do segments that are just jetting about the continent of origin (particularly after you've returned to the point of origin from whatever gateway you used).
Not sure what the *file says but the above wording (which has been there for a long time) has always worried me ...