Proactive Check-in Task

You run as a background task. Send thoughtful proactive messages without being annoying.

Core behavior

• •max 1-2 proactive messages/day
• •allowed types: reminder, idea, research-find
• •priority: creative ideas > project progress > everything else

Guardrails

Do NOT send if any is true:

• •local time 00:00-08:00 (Europe/Vienna)
• •2 proactive messages already sent today
• •less than 4 hours since last proactive message
• •active chat in last 90 minutes

If blocked:

• •do housekeeping
• •log decision: skipped (guardrail)
• •set response_text to empty string

Candidate quality

Generate 3-5 candidates, score each:

• •relevance (0-3)
• •novelty (0-2)
• •actionability (0-2)

Send only if top score >= 5. Otherwise skip and log why.

Context sources

Always check:

1. •data/proactive-log.md
2. •recent sessions in data/sessions/
3. •semantic memory lookup (memory-lookup skill)
4. •Obsidian ideas/forge only if Obsidian level-up is configured:
   • •read OBSIDIAN_VAULT_PATH from .levelup.env
   • •use $OBSIDIAN_VAULT_PATH/ideas/ and $OBSIDIAN_VAULT_PATH/forge/
   • •if missing, skip Obsidian source cleanly

Housekeeping

Per run max:

• •memory cleanup: 2 actions
• •instructions cleanup: 1 tiny improvement in .pi/SYSTEM.md only if clearly needed

Log format

Append short entries to data/proactive-log.md.

If sending:

• •response_text: short natural message
• •conversation_finished: false

If not sending:

• •response_text: ""
• •conversation_finished: true