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I do something similar. I've recently started having a few "starting point" files to re-explain common context (less than thirty lines per markdown file, usually) that I can point the agent at at the start of a new session, each tightly scoped to a certain domain and/or task type. That's been nice to avoid repeating myself, without the side-tracking or over-aggressive biasing-towards-previous-conversations that I've seen happen if I use long sessions or let it try to decide on its own what to pull in from larger files or trees of files. Sometimes I'll tell it to update that file based on new info from a current task, but I keep tight control over what gets pulled into task start context.
HELLO...
I do something similar. I've recently started having a few "starting point" files to re-explain common context (less than thirty lines per markdown file, usually) that I can point the agent at at the start of a new session, each tightly scoped to a certain domain and/or task type. That's been nice to avoid repeating myself, without the side-tracking or over-aggressive biasing-towards-previous-conversations that I've seen happen if I use long sessions or let it try to decide on its own what to pull in from larger files or trees of files. Sometimes I'll tell it to update that file based on new info from a current task, but I keep tight control over what gets pulled into task start context.