I've seen this in TS2010 Harlem line Route. Near South East towards the portal, the signal reads "Line ahead unsigalled".
The AI train stops there for a few seconds then the signal blinks green and the train goes on ahead to the portal. The setup there is the same setup as what you got.
What driver command did you use ? I used the "Navagate To" command for the AI train to get to the portal.
I think your example is different because of the length and you have a portal. I've tried all the driver commands.