Reliable web-agent monitoring is difficult when model-internal uncertainty signals such as token logits are unavailable. In this work, we study prefix-level risk prediction for web agents using observable trajectory signals: given an evolving prefix, estimate whether the current execution remains on track or is tending toward failure. We derive two observable trajectory representations: Macro features summarize cross-step agent--environment behavior and feedback, while Micro features measure the consistency of intention, action, and anticipated state change through repeated black-box queries. Instead of inheriting the final result label, we label the first critical error that remains uncorrected in the observed continuation and is associated with final failure as a key-step boundary, preserving valid early prefixes of failed trajectories as on track. Across WebArena-Lite and Online Mind2Web web agent benchmarks with five open- and closed-source backbones, observable trajectory signals are competitive with internal-signal baselines. The resulting predictors also support early intervention under fixed false-cut budgets and transfer across held-out website categories. These findings show that observable trajectory signals support valuable risk prediction abilities.
Long-horizon agents increasingly operate across many steps, tools, and observa- tions. In this setting, the relevant oversight question is not only whether each action is locally valid, but whether the evolving trajectory still corresponds to the task the user authorized. Drift can accumulate quietly: an agent may call the right tool with plausible arguments at every step, while its prefix moves toward a broader role, an adjacent objective, or evidence the user never supplied. Existing monitors mostly check local compliance, deliver final-trace verdicts, or score generic risk; they do not directly estimate this prefix-level relation. We introduce ontological trust, a task-conditioned property of trajectory prefixes, and instantiate it as RGE, an online monitor that decomposes trust along Role, Goal, and Evidence. RGE uses LLMs only to derive structured task and step representations; trust-state updates, projec- tions, and intervention decisions are deterministic, so the output is a replayable and auditable trust trajectory rather than a single end-to-end judge verdict. We construct a cross-domain trajectory corpus from OSWorld, FinanceBench, and EICU-AC, covering benign executions, prefix-paired drift, and pseudo-consistency failures. On this corpus, RGE outperforms adapted rule-, judge-, and shield-style baselines on prefix-paired drift detection. With the two larger estimator models, it exceeds 93% Drift F1 on every benchmark while keeping benign coverage at or above 95.8%. Pseudo-consistency is harder: detection depends on whether task completion is externally visible, a structural limit we characterize empirically.
Agentic systems entering production typically operate as partially integrated assemblies where structural defects, not task-level errors, dominate the failure landscape. At this maturity level, task-level error detection may be infeasible: structural failure modes mask the signal that task-level monitors are designed to detect.We present a monitoring and triage methodology that decomposes agentic system evaluation into three dimensions (quality, suitability, efficiency) at three monitoring scopes (within-run, cross-run, structural), using variance as a characterization signal. Findings are routed through severity classification adapted from FMEA, concentrating human attention on the subset that warrants investigation. We evaluate on a synthetic testbed of 220 runs across 120 document bundles with controlled error injection.Three results emerge. Monitor scope determines failure type: within-run monitors surface deterministic stage defects (CV = 0.02), cross-run monitors surface stochastic integration consequences (CV = 1.25, 24% at L2), and a structural monitor identifies an integration gap with perfect consistency (CV = 0.00). Injected task-level errors are indistinguishable from clean baselines, confirming structural defects mask task-level signal. Deterministic triage routes 97% of findings to automated tracking, leaving the 2% reflecting variable behavior for human investigation.We propose, on Stage 1 evidence, a maturity-staging model in which monitoring transitions from structural characterization to error detection to reliability tracking as integration defects resolve. The taxonomy, CV-based scope characterization, and severity model transfer architecturally to document-driven, multi-stage agentic workflows in regulated industries; specific calibrations are domain-specific. Deploy monitoring early: the first thing it finds is the most important thing to fix.