@Mads_Mortensen
Seems to be a Bug once you change the prefixes/patterns! I just checked again for you.
@miguel
Delete both Outbound Routes and create again! Should work then. Do not change. Create new.
Problem/to replicate:
Create 2 Outbound Routes
One for Trunk A other for Trunk B
Trunk A Prefix 99 Pattern X.
Trunk B no Prefix Pattern X.
Save and test. Works
If you then change Prefix 99 to 88 and save it will stop working. Will go the wrong Trunk.
So editing Outbound Routes causes issues.