Can't go:

Can't go:

Free to go:

The issue is when the train has a choice between chain and block signals after a chain signal. If the chain signal path is shorter it will never consider the open block signal path which allows the train to get closer to it's destination. If the block signal path is shorter, it will happily select this path. A second oddity in this scenario is if the paths are equal length as shown in the picture the train will take the path which is shortest to the intermediate signal. The train does not reconsider it's path, it sits waiting forever. This bug was confirmed by another user in the factorio IRC.