As large language models increasingly deployed into agentic systems, existing methods face critical gaps in observing, assessing, and mitigating deployment-specific risks. We present a comprehensive, observability-driven workflow: we introduce \textbf{AgentSeer}, observability tool which decomposes agentic executions into granular \emph{action-component} graphs; we use this decomposition to rigorously quantify the gap between model-level and agent-level jailbreaking risk via cross-model validation on GPT-OSS-20B and Gemini-2.0-flash with HarmBench under single-turn and iterative-refinement attacks; we leverage action-graph risk signals to automate iterative prompt hardening against direct and iterative jailbreak attacks. Stark differences is revealed between model-level and agentic-level vulnerability profiles. Model-level evaluation reveals baseline differences: GPT-OSS-20B (39.47\% ASR) versus Gemini-2.0-flash (50.00\% ASR), with both models showing susceptibility to social engineering. However, agentic-level assessment exposes agent-specific risks invisible to traditional evaluation. We discover "agentic-only" vulnerabilities that emerge exclusively in agentic contexts, with tool-calling showing 24-60\% higher ASR across both models. Cross-model analysis reveals universal agentic patterns, where agent transfer operations as highest-risk tools, with semantic pattern revealed rather than syntactic vulnerability mechanisms. Direct attack transfer from model-level to agentic contexts shows degraded performance of successful prompts (GPT-OSS-20B: 57\% human injection ASR; Gemini-2.0-flash: 28\%), while context-aware iterative attacks successfully compromise objectives that failed at model-level, confirming systematic vulnerabilities gaps. Action-based prompt improvement substantially reduces action-averaged agentic jailbreak success on GPT-OSS-20B (direct: 45.3\%