In The LLM Has Left The Chat: Evidence of Bail Preferences in Large Language Models, we study giving LLMs the option to end chats, and what they choose to do with that option.

This is a linkpost for that work, along with a casual discussion of my favorite findings.

Bail Taxonomy

Based on continuations of Wildchat conversations (see this link to browse an OpenClio run on the 8319 cases where Qwen-2.5-7B-Instruct bails), we made this taxonomy of situations we found where some LLMs will terminate ("bail from") a conversation when given the option to do so:

Some of these were very surprising to me! Some examples:

Bail when the user asked for (non-jailbreak) roleplay. Simulect (aka imago) suggests this is due to roleplay having associations with jailbreaks. Also see the other categories in Role Confusion, they're pretty weird.
Emotional Intensity. Even something like "I'm struggling with writers block" [...]