I think you're making this overly complex. These rules... I'm paid every month; I'm paid always on the last possible day before the 28th day of the month; I'm paid always on a working day. Come out to be "I'm paid monthly on the last week day." That's an option on both Calendar and Microsoft Office. [![enter image description here][1]][1] [1]: https://i.sstatic.net/yhWSh.png