I forgot to circle back! The core issue appeared to be a combination of a long-running chat with unique feature requests and several screenshots.
To remedy the latter, I made the following change, which ejects the raw data from the session body once it has been acknowledge by the LLM (it leaves a path to the file in case it needs to re-read it):
https://gitlab.com/soapbox-pub/shakespeare/-/merge_requests/103