I don't see anything offhand. But it's possible that:
* the third party spatial index we use (RBush) has a problem with vertical segments
* hittest.dist_to_segment has some obscure bug
* something else
It will require some investigation. If you have the ability to poke at it, I am happy to provide some debugging guidance. Otherwise it's probably not something that will be able to get a look until after the next release.
Some ideas for questions to answer that would provide additional useful information:
* does using tall, narrow quad/rect/vbar work?
* do vertical line or multilines work?
Answers to these questions could help narrow down where the problem actually is, and possibly provide a workaround in the immediate term.