This is a wierd one.
Gave a cargo fleet and colony fleet similar orders, separated by a month (so the cargo arrives first).
Path is Sol - New York - Nexus 755 - Boston - Miami - Oklahoma - Memphis
Sol obviously is the origin of the infrastructure and colonists. There are existing colonies in NY, Boston and Miami. Jump Gates exist between all links except Oklahoma - Memphis.
On the screenshot, you will notice that the fleet is in Boston, however, the order queue thinks the fleets is still in Sol.
The order sequence is Load at Earth, Transit NY, Transit N755, Transit Boston, Refuel Far Station (Boston colony), Transit Miami, Transit OK, Transit Memphis, Unload at Memphis, Transit OK, Transit Miami, Transit Boston, Refuel Far Station, Transit N755, Transit NY, Transit Sol, Refuel Earth.
I then hit repeat (4). Not four times, but change the 1 to 4 and hit repeat so I get 5 iterations of the orders.