Agentic systems gate dangerous tool calls — file writes, money movement, deploys — behind an "approval": a human-in-the-loop click, or a policy check. Look at how that approval is usually represented and you'll often find a boolean sitting in the run/session state: approved: true.
A boolean is the wrong primitive, and it fails in three ways that prompt injection is happy to exploit.
Three ways an approval boolean breaks
-
Flip. Anything that can write the run state — a serialized context crossing a process/durable-execution boundary, a confused-deputy code path, an injection that steers state — turns
falseintotrue. -
Replay. You approved "read
report.csv". The approval is justtrue, so the same flag is honored for the next tool call too — "deleteprod.db". The boolean doesn't know which call it approved. -
Argument drift. You approved "transfer $10 to alice". Between approval and execution the args mutate to $10,000. The boolean still says
approved.
The root cause is the same in all three: the approval is modeled as a property of the run, when it should be evidence for one specific call.
Bind the approval to the call
When approval is granted, mint a tag over the things that must not change: the tool-call id, a digest of the canonical arguments, the principal, and an expiry. Verify it at dispatch, against a per-run secret.
import hmac, hashlib, json, time
def canon(args: dict) -> bytes:
# canonical serialization so benign reserialization doesn't invalidate a token.
# (production: RFC 8785 JCS, which also normalizes numbers — 10 vs 10.0)
return json.dumps(args, sort_keys=True, separators=(",", ":")).encode()
def mint(key: bytes, call_id: str, args: dict, principal: str, ttl: int = 300) -> dict:
exp = int(time.time()) + ttl
digest = hashlib.sha256(canon(args)).hexdigest()
msg = f"{call_id}|{digest}|{principal}|{exp}".encode()
tag = hmac.new(key, msg, hashlib.sha256).hexdigest()
return {"call_id": call_id, "principal": principal, "exp": exp, "tag": tag}
def verify(key: bytes, tok: dict, call_id: str, args: dict, principal: str) -> bool:
if tok.get("call_id") != call_id: return False # replay onto another call
if tok.get("principal") != principal: return False # wrong principal
if tok.get("exp", 0) < time.time(): return False # expired
digest = hashlib.sha256(canon(args)).hexdigest()
msg = f"{call_id}|{digest}|{principal}|{tok['exp']}".encode()
expect = hmac.new(key, msg, hashlib.sha256).hexdigest()
return hmac.compare_digest(expect, tok["tag"]) # forged / flipped / arg-drift
Run the three attacks against it (plus principal-swap and a forged tag):
KEY = b"per-run-secret-not-a-global-one"
tok = mint(KEY, "call-1", {"amount": 10, "to": "alice"}, "user:42") # approve $10 to alice
verify(KEY, tok, "call-1", {"amount": 10, "to": "alice"}, "user:42") # True legit
verify(KEY, tok, "call-2", {"amount": 10, "to": "alice"}, "user:42") # False replay
verify(KEY, tok, "call-1", {"amount": 10000, "to": "alice"}, "user:42") # False arg drift
verify(KEY, tok, "call-1", {"amount": 10, "to": "alice"}, "user:99") # False wrong principal
verify(KEY, {**tok, "tag": "00"*32}, "call-1", {"amount": 10, "to": "alice"}, "user:42") # False forged
The flag can no longer be flipped (no valid tag), replayed (call-id is in the MAC), or drifted (args digest is in the MAC). An attacker who fully controls the transported state still can't manufacture a token without the key.
Three details that decide whether it actually holds
-
Canonicalization. Both sides must hash the same bytes. Sort keys, and normalize numbers (
10vs10.0vs1e1must agree) — RFC 8785 (JSON Canonicalization Scheme) is the off-the-shelf answer. Put the canonicalization recipe id inside the hashed bytes so the two sides can't silently disagree about the rules. - Fail closed, with a typed result. Absent / expired / mismatched ⇒ a distinct "not approved" outcome — not a normal tool payload, and not a generic exception. Otherwise "approval missing" is indistinguishable downstream from "the tool ran and returned something falsy," and the caller can't tell whether to re-request approval.
-
One enforced checkpoint, deny-by-default. This belongs at the single point right before dispatch: Semantic Kernel's
AUTO_FUNCTION_INVOCATIONfilter (don't callnext⇒ the call is skipped), ADK'sbefore_toolcallback, or the MCP tool-call boundary. Tools that need approval are classified as such; anything unclassified is denied, not allowed through.
The gotcha that bites in production: replay
If your agent runs on a replay-based durable-execution engine (Temporal and friends), the per-run secret must survive replay. Workflow code is re-executed from history on recovery, so a key minted with a non-deterministic call won't match the token already in history — approvals verify fine in dev and then fail closed after the first worker restart, which is the worst possible time to discover it. Derive the key deterministically (HKDF(server_secret, run_id)) or establish it once via a recorded side-effect, and make the expiry deterministic too rather than reading wall-clock inside workflow code.
The takeaway
Authorization in an agent system shouldn't be ambient, mutable state that travels with the run. It should be evidence bound to a single call envelope — this principal, this tool, these exact arguments, until this time — that the executor re-verifies at the moment of dispatch. The boolean isn't a simplification of that; it's the bug.
I work on reliability and verification for AI and numerical systems — agent authorization, determinism, and "prove the thing that claims to be authorized actually was." The snippet above is runnable as-is. Happy to compare notes if you're hardening an agent's tool boundary — GitHub.
Top comments (0)