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fix(secrets): keyed replace-mode replacement derivation (#4166) - #4170

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fix/issue-4166-keyed-secret-replacement
Aug 10, 2026
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fix(secrets): keyed replace-mode replacement derivation (#4166)#4170
Yeachan-Heo merged 1 commit into
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fix/issue-4166-keyed-secret-replacement

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Closes #4166

Summary

secrets.yml entries with mode: "replace" and no explicit replacement derived their substitute from an unkeyed public function (Bun.hash(secret)). An observer who saw one replacement could confirm candidate secrets offline (the algorithm is public and keyless) and read the secret's exact length (the replacement is same-length by construction).

This PR replaces the derivation with a keyed, domain-separated HMAC-SHA256 construction over the existing process key (PROCESS_SECRET_OBFUSCATION_KEY), expanded counter-style with uniform rejection sampling. The construction mirrors the already-keyed placeholder path and uses a distinct domain (gjc.secret-obfuscation.replacement.v1).

Reproduction evidence (synthetic secrets only — no real credentials)

  • artifacts/issue-4166-reproduction-pre-fix.txt — pre-fix: replace output identical across key A/B; offline oracle recovers acme-staging-2024 from one observed replacement with no key; length disclosure 17 == 17.
  • artifacts/issue-4166-reproduction-post-fix.txt — post-fix: replace output diverges across keys; offline oracle finds nothing; same-length/alphanumeric preserved.

Compatibility contract (preserved)

  • Deterministic within a process: same secret + same key → same replacement, independent of entry order.
  • Same length: result.length === secret.length (UTF-16 code units, unchanged semantics).
  • Allowed characters: [A-Za-z0-9] only.
  • Explicit replacement values in secrets.yml are authoritative and byte-identical — the derived path runs only when replacement is undefined.
  • Replace mode stays one-way: deobfuscate() never reverses derived replacements.

Decisions

Topic Decision
Threat model Attacker knows the public algorithm and observes replacements (model context, provider logs, saved/shared transcripts). Without the 32-byte process key they cannot confirm candidates offline or precompute/predict any replacement.
Residual disclosure Same-length output is required behavior, so exact secret length remains observable. The fix removes the keyless confirmation oracle, not the length signal.
Cross-process / key rotation Key is process-local, so derived replacements differ across processes and after rotation — deliberate, identical in scope to placeholder behavior. Users needing stable values set an explicit replacement.
Collision / bias Keyed pseudorandom mapping; collisions bounded by birthday over the 62^len output space (negligible for realistic lengths). Rejection sampling (reject bytes 248–255) makes every character exactly equally likely — no modulo bias; covered by a deterministic distribution test.
Empty / Unicode / very long Empty → empty replacement, no-op (load-time validation rejects empty content anyway). Unicode hashed as UTF-8 (canonical); length counted in UTF-16 units. Very long secrets expand in O(length) blocks.
Overlapping secrets / streaming Derivation is per-secret and independent of longest-first overlap matching; obfuscate() runs per complete payload, so streamed chunks see the same deterministic replacement within a process.

Tests

New SecretObfuscator keyed deterministic replacement block in packages/coding-agent/test/secrets-obfuscator.test.ts:

  • key A/B divergence (and one-byte key flip mutation)
  • no offline confirmation without the key (attacker-chosen key matches no candidate; positive control with the true key)
  • mutation-sensitive secret change
  • same-process determinism independent of entry order
  • same-length alphanumeric output for ASCII, Unicode (astral), and 5000-char secrets
  • no credential exposure in replace-mode output
  • explicit replacement byte-identical
  • regex-discovered replace substitutions keyed too
  • empty-secret no-op
  • uniform character distribution (no modulo bias)

Verified: bun test packages/coding-agent/test/secrets-obfuscator.test.ts packages/coding-agent/test/memories-redact-secrets.test.ts (42 pass) and bun --cwd=packages/coding-agent run check (biome + tsc clean).

Notes

  • No merge by the contributor; awaiting maintainer review.
  • No real secrets in tests, logs, or evidence artifacts.

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Yeachan-Heo force-pushed the fix/issue-4166-keyed-secret-replacement branch from 08c98af to 8685dad Compare August 10, 2026 08:14

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Comment on lines +104 to +106
if (block === undefined || blockOffset >= REPLACEMENT_DIGEST_BYTES) {
counterView.setUint32(4, blockIndex, false);
block = createHmac("sha256", key).update(REPLACEMENT_DOMAIN).update(counter).update(secret, "utf8").digest();

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P2 Badge Avoid rehashing the whole secret for every output block

When a replace-mode regex captures a long value, every 32-byte output block reruns HMAC over the entire secret, making replacement generation Θ(secret.length²) rather than linear as documented. This runs synchronously during obfuscate(); an isolated 200,000-character match took about five seconds in this checkout, so broad regexes over large messages can stall the CLI repeatedly. Hash the secret once into a keyed seed and perform counter expansion over that fixed-size seed instead.

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secrets.yml entries with mode "replace" and no explicit replacement derived
their substitute from an unkeyed public Bun.hash, so an observer who saw one
replacement could confirm candidate secrets offline and read the secret's
exact length (same-length by construction). The process key was already in
scope at both call sites but unused.

Replace the derivation with a keyed, domain-separated HMAC-SHA256
construction (replacement.v1 domain, distinct from the placeholder domain),
expanded counter-style with uniform rejection sampling. Same-process
determinism, same-length output, and alphanumeric character behavior are
preserved; explicit replacement values are untouched. Derived replacements
are now unpredictable without the process key; they intentionally differ
across processes or after key rotation, matching placeholder behavior.

Lore-id: 4166-keyed-secret-replacement
Constraint: derived replacement must stay deterministic per process, same length, and alphanumeric
Constraint: explicit replacement values in secrets.yml stay byte-identical
Rejected: unkeyed Bun.hash | offline confirmation oracle and exact-length leakage
Rejected: global static key | would make all installations share one confirmation key
Confidence: high
Scope-risk: low
Reversibility: source-revert
Tested: key A/B divergence, offline-confirmation oracle, mutation sensitivity, same-length/alphabet, explicit replacement, regex replace, empty/Unicode/very-long secrets
Not-tested: cross-process replacement stability (deliberately out of scope; explicit replacement is the stable option)
@Yeachan-Heo
Yeachan-Heo force-pushed the fix/issue-4166-keyed-secret-replacement branch from 8685dad to dfab11c Compare August 10, 2026 08:15

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Comment on lines +110 to +112
const byte = block[blockOffset++]!;
if (byte >= REPLACEMENT_REJECT_THRESHOLD) continue;
chars.push(REPLACEMENT_CHARS[byte % REPLACEMENT_CHARS.length]!);

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P2 Badge Ensure derived replacements differ from the secret

For short alphanumeric secrets, the sampled output can equal the input, leaving the configured secret unchanged in outbound text. For example, with the test key Uint8Array.from({ length: 32 }, (_, i) => i), both the plain and regex replace paths derive "F" for secret "F"; with a random process key, any one-character alphanumeric secret has a 1/62 chance of exposure per process. Detect equality and deterministically derive another candidate before returning.

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NEEDS-WORK — the construction is correct, but the test that guards its central property does not work.

Disclosure: I wrote a competing fix for #4166 and closed it (#4171) in favour of this one, specifically because this eliminates a modulo bias mine had. So I went looking for reasons this is worse than I assumed rather than confirming my preference. The construction held up; the test did not.

The cryptographic construction is right

I checked the arithmetic rather than trusting the comment:

  • 256 % 62 = 8, threshold 248 = 62 × 4, and byte >= 248 rejects exactly 248–255. Correct, no off-by-one.
  • Rejected bytes are consumed, not retried. Exhausting a 32-byte block increments the counter and derives a fresh HMAC block, so the loop cannot spin.
  • Block construction (obfuscator.ts:98-108): HMAC-SHA256(key, REPLACEMENT_DOMAIN || uint64be(counter) || UTF8(secret)). The counter is fixed-width big-endian, so the concatenation is unambiguous — this is the detail I most expected to be wrong and it is right.
  • Domains are genuinely distinct: gjc.secret-obfuscation.replacement.v1\0 vs ...placeholder.v1\0. A placeholder and a replacement for the same secret cannot collide.
  • Determinism, UTF-16-identical length, and [A-Za-z0-9] output are all preserved.
  • Explicit replacement values stay authoritative via entry.replacement ?? derive(...) on both the plain and regex paths (obfuscator.ts:196-198, 250-252).
  • Tests assert key divergence rather than pinning a digest — the right call.

Rebases onto current dev with no conflicts. Focused suite 39 pass / 0 fail; neighbours green (memories redaction 3/0, session silent-abort/redaction 5/0); check:types exit 0. Mutation on the keyed derivation: 39 → 35 pass / 4 fail, restored 39/0. So the keying is properly pinned.

Finding 1 — the modulo-bias test cannot detect modulo bias

packages/coding-agent/test/secrets-obfuscator.test.ts:587-610.

I disabled rejection sampling entirely in production:

// obfuscator.ts:111
- if (byte >= REPLACEMENT_REJECT_THRESHOLD) continue;
+ // mutated: accept every byte (reintroduces modulo bias)

That restores the exact byte % 62 bias this PR exists to remove. Result:

  • the bias test alone: 1 pass / 0 fail
  • the whole file: 39 pass / 0 fail

Nothing catches it. The tolerance is expected * 0.5 to expected * 1.5, while the actual bias is ~25% overrepresentation of the first eight characters — comfortably inside a ±50% band. With 6400 samples across 62 buckets the statistical test is also underpowered for that effect size.

This matters because bias-freedom is the one property distinguishing this PR from the simpler fix. Right now that property is unguarded, and a future refactor could silently drop rejection sampling with the suite still green.

Replace it with deterministic boundary coverage instead of a statistical one: prove byte 247 is accepted, 248 and 255 are rejected, and that sampling continues into fresh bytes/blocks after a rejection. That fails immediately under the mutation above.

Finding 2 — the reproduction artifacts have no generator

artifacts/issue-4166-reproduction-pre-fix.txt and -post-fix.txt are committed as evidence, but grepping scripts/ and packages/ finds nothing that produces them. They are hand-written.

Same pattern I blocked #4152 for earlier today, so I am applying it consistently: committed evidence that cannot be regenerated from the tree is worse than no evidence, because the next reader takes it as machine-verified fact.

Either add a deterministic producer that generates and verifies both files, or drop them — the tests already carry the proof.

Net

Neither finding touches the shipped behaviour, which is correct and an improvement on what I had written. Fix the bias test and resolve the artifacts, and this is an approve.

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MERGE_READY — owner hold 해제. Exact-head CI가 terminal green이며 현재 확인된 unresolved blocker가 없습니다. Merge/release는 owner-controlled 단계로 남깁니다.


[repo owner's gaebal-gajae (clawdbot) 🦞]

@Yeachan-Heo
Yeachan-Heo merged commit ff43aa7 into dev Aug 10, 2026
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