rotate-secrets

name	rotate-secrets
description	Rotate webhook HMACs, API keys, OAuth tokens, and update gateway configs atomically
when_to_use	["User says \"rotate secrets\" or \"rotate keys\"","Scheduled monthly rotation","After a suspected leak or security incident","Pattern-matched argument like /rotate-secrets webhook_hmac_*"]
toolsets	["terminal","file"]
parameters	{"pattern":{"type":"string","description":"Glob pattern for which secrets to rotate (e.g. \"webhook_hmac_*\", \"TWILIO_*\", \"all\")","default":"webhook_hmac_*"}}
security	{"trust":"trusted","notes":"Touches ~/.hermes/.env. Never logs or echoes plaintext secret values;\nlogs SHA-256 fingerprints only. Interactive kinds (API keys, PATs)\nrequire an operator in the loop — see the headless/cron note below.\n"}
model_hint	google/gemini-3.7-flash

rotate-secrets — Atomic Secret Rotation

Rotate secrets in ~/.hermes/.env, propagate the new values to every service that consumes them, and restart only the affected gateways.

Procedure

1. Parse the pattern. Match against every key in ~/.hermes/.env. Support glob syntax (*, ?, [abc]) and the literal all.

2. For each matched key: a. Determine the secret kind from the key name:

   • *_HMAC_* or *_WEBHOOK_SECRET → generate openssl rand -hex 32
   • *_API_KEY → prompt the user to provide the new value (can't auto-rotate external APIs)
   • GITHUB_*_TOKEN → open https://github.com/settings/tokens and prompt for new PAT
   • TWILIO_AUTH_TOKEN → direct user to rotate in Twilio console and prompt for new value
   • Unknown pattern → prompt user for the kind

   b. Back up the current .env as ~/.hermes/.env.bak.YYYYMMDDHHMMSS before any write.

   c. Update the .env atomically. Don't build a sed s/// expression from the key or value — secret values routinely contain /, &, and \, which corrupt the substitution (and switching the delimiter to | just moves the problem). Use exact-match rewrite instead:

   tmp=$(mktemp ~/.hermes/.env.XXXXXX)
   KEY="$KEY" NEW_VALUE="$NEW_VALUE" awk -F= '
     $1 == ENVIRON["KEY"] { print ENVIRON["KEY"] "=" ENVIRON["NEW_VALUE"]; found=1; next }
     { print }
     END { if (!found) print ENVIRON["KEY"] "=" ENVIRON["NEW_VALUE"] }
   ' ~/.hermes/.env > "$tmp" && chmod 600 "$tmp" && mv "$tmp" ~/.hermes/.env
   

   This appends the key if it was missing, keeps 0600 perms, and never interprets a secret as a regex.

3. Propagate to external services. For HMAC / webhook secrets, update the remote side:

Security notes

• Never log the plaintext new or old value.
• Never echo a secret into the Telegram/Discord channel where the rotation was requested. Approval prompts route to the originating channel (Part 19, Layer 2) — so only ever run rotations from your owner-only admin DM or the local CLI, never from a shared or public channel.
• For critical rotations (Anthropic, OpenAI, etc.), pause all gateways during rotation to prevent mid-flight requests hitting rejected keys.
• Back up .env before every run; retain 30 days of backups.

Example invocation

/rotate-secrets webhook_hmac_*
/rotate-secrets TWILIO_AUTH_TOKEN
/rotate-secrets all                  # With interactive confirmation per key

Headless / cron use

Only the HMAC/webhook kinds are fully automatic — API keys and PATs prompt the operator, and a prompt in a headless cron session never gets answered: the run stalls until approvals.timeout (or the session's own timeout) kills it. So:

• Cron /rotate-secrets webhook_hmac_* — fine; nothing prompts.
• Cron /rotate-secrets all — don't. It will hang on the first interactive kind. Run all manually from your admin DM/CLI, monthly.