The problem occurs on months with 4 Fridays only.
The monthly is configured to run on the last Friday of the month.
On the monthly under Schedule I have checked "Run according to schedule and run according to rules for this template". Under Schedule Details, under Run Day Options I have selected "Week Days" and checked the box for Last Friday. The Effective Date is in the past. The Time Window is set identical to the weekly.
As I stated in my original post, the rule is in place for the monthly to take precedence over the weekly if there is a conflict.