LGTM. Right shape: the flag is SDK-internal, never projects to the wire, and the validator's short-circuit is correctly narrow (sender is None AND supervisor is None) so wiring an SDK sender still triggers full RFC 9421 introspection.

Things I checked

• webhook_signing_managed_externally lives at the top level of DecisioningCapabilities (platform.py:181), not inside the WebhookSigning Pydantic model. The projection at handler.py:1697-1700 only dumps caps.webhook_signing.model_dump(...) — flag has zero wire reachability. Pinned by the new projection test at test_decisioning_capabilities_projection.py:360-365.
• Bypass safety: isinstance(adopter_managed, bool) at webhook_emit.py:447 fail-closes on truthy strings, ints, numpy.bool_, etc. The subsequent adopter_managed is True at L462 is defense-in-depth — identity, not equality, so 1 == True doesn't sneak through.
• Wired-sender precedence: short-circuit at L462 requires sender is None and supervisor is None. A bearer-token sender wired alongside webhook_signing_managed_externally=True still trips the non-JWK gate at L511 — pinned by test_adopter_managed_flag_does_not_bypass_wired_sender_validation.
• Request-scoped path: handler.py:1624 re-runs the validator per-request when get_adcp_capabilities_for_request returns scoped caps, so per-tenant flag flipping works as documented. _validate_scoped_capabilities_static_contract constrains only specialisms and supported_protocols, leaving the new flag free to vary per-tenant (intended).
• Conventional commit feat: is correct. New field is keyword-defaulted (bool = False); no public-API break, no ! required.
• RequestContext.metadata / _build_request_context / credential-shaped key suffix list untouched. No credential-leak surface change.
• Spec compliance: AdCP webhook_signing.supported=true binds the seller to RFC 9421, not the SDK specifically. Moving the contract from SDK-validated to operator-asserted is spec-legal.

Follow-ups (non-blocking — file as issues)

• INFO vs WARNING on the bypass log. webhook_emit.py:463 emits at INFO, but every sibling skip-path in this file uses WARNING (L170, L253, L279, L295, L321, L480) — including the structurally identical "we skipped validation, you own the contract" branch at L480. A fat-fingered webhook_signing_managed_externally=True on a broken external signer should be the loudest line in boot logs, not the quietest. (security-reviewer-deep: Low.)
• Validator docstring drift. webhook_emit.py:399-437 still describes unconditional fail-fast; the new bypass lives only in the body. Add a sentence naming the webhook_signing_managed_externally carve-out so a reader auditing the contract via the docstring sees the operator-owned escape hatch. (ad-tech-protocol-expert-deep.)
• Test gap on the supervisor path. New tests cover sender=None+supervisor=None (passes) and sender=bearer+supervisor=None (still fails). Missing: supervisor=InMemoryWebhookDeliverySupervisor(bearer_sender) + sender=None + adopter_managed=True — should still fail, since the SDK is doing the signing. The behavior is correct (the supervisor path at L471-L489 doesn't re-consult the flag); the test is the gap.
• Optional: scoped-caps gate symmetry. _validate_scoped_capabilities_static_contract (handler.py:976) blocks scoped caps from changing specialisms / supported_protocols. Consider extending to reject scoped caps enabling webhook_signing.supported=True when static caps had it disabled — would close the per-tenant trust-surface expansion. Not a security hole today (failure is loud on the buyer side, contained to the asserting tenant), but symmetric with the existing guard.

Approving on the strength of the fail-closed non-bool guard plus the narrow short-circuit condition.