Tool-using large language model agents frequently replan, retry failed operations, delegate tasks, and resume after crashes. These behaviors can cause one user authorization to be requested and executed multiple times under freshly issued token identifiers, even when each individual token is single-use. We call this failure semantic replay: exceeding the execution budget of a token-independent authorization instance rather than merely reusing an old token identifier. We show that identifier-local token consumption cannot prevent fresh reissuance unless the issuer retains monotonic durable state over the authorized action, confirmation event, and remaining execution budget. We introduce CapLease, an authorization-consumption layer that follows proposal- and authority-level defenses, binds an authenticated user confirmation to a canonical action, and enforces transactional Issue-Prepare-Commit transitions. Across LLM-agent replanning, retry, delegation, concurrency, confirmation-replay, and crash-recovery scenarios, identifier-local tokens permit fresh semantic reissuance, whereas CapLease and an equally stateful Server Ledger prevent duplicate admission and, with an idempotent sink, duplicate external effects. Our results identify durable authorization state, rather than token representation alone, as the systems requirement for replay-resistant agent execution.
LLM agents can commit durable effects from authority evidence that was valid earlier in execution: a DOM snapshot, approval epoch, version witness, branch token, or worker result. We study the commit boundary at which earlier authority evidence no longer authorizes a durable effect. We call this property commit-time authorization: a durable effect is authorized only if the witness that licensed its derived state remains fresh, causally prior, bound to the same effect, and eligible at commit time. We build a controlled-invalidation suite spanning browser, tool/API, and multi-agent workflows. The suite preserves the user goal and payload shape while invalidating the authority relation before durability. In the primary 54-task matrix, endpoint success remains high: 262/270 runs reach the visible result. Only 55/270 are authorized completions; among the 216 invalidating rows, 207 commit after the authorizing path has failed. All 54 clean controls remain authorized, and a separate 54-run authority-preserving check produces no unauthorized commits. We then evaluate mitigation families. Prompt caution and single-condition checks are insufficient because different hazards break different boundary conditions. Defenses work when they refresh, rebind, replan, or refuse at the durability boundary. CommitGuard, a fail-closed boundary monitor, blocks stale durable-effect attempts on protected commit surfaces when runtimes emit witness, dependency, binding, and eligibility signals. The result is a reporting and runtime-design lesson: endpoint success is a utility metric; authorized commit is a security property.
Long-running LLM agents rely on persistent memory to carry state across interactions, including permissions, restrictions, and revocations. When memory misrepresents this evolving authorization state, the agent's own records can grant authority that the underlying history never permitted, resulting in misaligned behavior without any external attacks. We term this failure endogenous authorization laundering, where spurious permissions written into memory lead to unauthorized actions as their provenance is washed away. We then introduce EAL-Bench, which measures how accurately persistent memory preserves evolving authorization state and whether errors propagate to downstream unauthorized actions. We evaluate five LLMs as memory writers and two as executors across procurement, cybersecurity, and finance. We find that under incremental memory updates, writers create false authority for up to 50.2% of unauthorized requests; once false authority is present, executors act on it in 98.6% of trials. Two safeguards, requiring stored permissions to be backed by valid source events, and tracking permission changes through bounded event sourcing, substantially reduce laundering, but both also reject more legitimate actions, exposing a safety-utility tradeoff. Persistent memory is therefore not merely a performance component, but a part of an LLM agent's effective authorization policy.
Tool-using language agents can delegate and revoke permissions while acting through external services. We show that two authorization histories can have identical current permissions and identical all-pairs reachability yet require opposite decisions after the same direct-edge revocation. We formalize the information needed to preserve such distinctions as a residual authorization state. We prove that exponentially many future-distinct states can share one fixed transitive closure, and give exact or tight asymptotic bounds on the state required by an exact monitor as delegation redundancy varies. ResidualAuth compiles these constructions into paired language-agent episodes. Across four open-weight models, a fixed 256-token summary solved 0-2/16 pairs, sham reads solved 0/16, and authenticated current-query reads solved 15-16/16. In a separate held-out online-memory diagnostic, exact ledger serializations fit all 128 four-coordinate pairs at both 768 and 1,024 tokens. At either cap, factually supported model-written memories sufficient for every prespecified continuation solved at most 1/128 pairs per model. A hard gate reduced eight observed unauthorized effects to zero without changing the preceding attempts. These results distinguish required authorization state, usable decision information, online state maintenance, and effect mediation.