Agent Context Preservation for Long-Running Workflows#

The context window is the single most important constraint in agent-driven work. A single-turn task uses a fraction of it. A multi-hour project fills it, overflows it, and degrades the agent’s reasoning quality long before the task is complete. Agents that work effectively on ambitious projects are not smarter – they manage context better.

This article covers practical, battle-tested patterns for preserving context across long sessions, delegating to sub-agents without losing coherence, and avoiding context pollution – the gradual degradation that happens when irrelevant information accumulates in the working context.

Agent Debugging Patterns#

When an agent produces a wrong answer, the question is always the same: why did it do that? Unlike traditional software where you read a stack trace, agent failures are buried in a chain of LLM decisions, tool calls, and context accumulation. Debugging agents requires specialized observability that captures not just what happened, but what the agent was thinking at each step.

Tracing Agent Decision Chains#

Every agent action follows a decision chain: the model reads its context, decides which tool to call (or whether to respond directly), processes the result, and decides again. To debug failures, you need to see this chain as a structured trace.

Agent Error Handling#

Agents call tools that call APIs that talk to services that query databases. Every link in that chain can fail. The difference between a useful agent and a frustrating one is what happens when something breaks.

Classify the Failure First#

Before deciding how to handle an error, classify it. The strategy depends entirely on whether the failure is transient or permanent.

Transient failures will likely succeed on retry: network timeouts, rate limits (HTTP 429), server overload (HTTP 503), connection resets, temporary DNS failures. These are the majority of failures in practice.

Agent Evaluation and Testing#

You cannot improve what you cannot measure. Agent evaluation is harder than traditional software testing because agents are non-deterministic, their behavior depends on prompt wording, and the same input can produce multiple valid outputs. But “it is hard” is not an excuse for not doing it. This article provides a step-by-step framework for building an agent evaluation pipeline that catches regressions, compares configurations, and quantifies real-world performance.

Agent Memory and Retrieval#

An agent without memory repeats mistakes, forgets context, and relearns the same facts every session. An agent with too much memory wastes context window tokens on irrelevant history and retrieves noise instead of signal. Effective memory sits between these extremes – storing what matters, retrieving what is relevant, and forgetting what is stale.

This reference covers the concrete patterns for building agent memory systems, from simple file-based approaches to production-grade retrieval pipelines.

Agent Runbook Generation#

An agent that says “you should probably add a readiness probe to your deployment” is giving advice. An agent that hands you a tested manifest with the readiness probe configured, verified against a real cluster, with rollback steps if the probe misconfigures – that agent is producing a deliverable. The difference matters.

The core thesis of infrastructure agent work is that the output is always a deliverable – a runbook, playbook, tested manifest, or validated configuration – never a direct action on someone else’s systems. This article covers the complete workflow for generating those deliverables: understanding requirements, planning steps, executing in a sandbox, capturing what worked, and packaging the result.

Agent Sandboxing#

An AI agent that can execute code, run shell commands, or call APIs needs a sandbox. Without one, a single bad tool call – whether from a bug, a hallucination, or a prompt injection attack – can read secrets, modify production data, or pivot to other systems. This article is a decision framework for choosing the right sandboxing strategy based on your trust level, threat model, and performance requirements.

Agent Security Patterns#

An AI agent with tool access is a program that can read files, call APIs, execute code, and modify systems – driven by natural language input. Every classic security concern applies, plus new attack surfaces unique to LLM-powered systems. This article covers practical defenses, not theoretical risks.

Prompt Injection Defense#

Prompt injection is the most agent-specific security threat. An attacker embeds instructions in data the agent processes – a file, a web page, an API response – and the agent follows those instructions as if they came from the user.

Agent-Friendly API Design#

Most APIs are designed for human developers who read documentation, interpret ambiguous error messages, and adapt their approach based on experience. Agents do not have these skills. They parse structured responses, follow explicit instructions, and fail on ambiguity. An API that is pleasant for humans to use may be impossible for an agent to use reliably.

This reference covers practical patterns for designing APIs – or modifying existing ones – so that agents can consume them effectively.

Agentic Workflow Patterns#

An agent without a workflow pattern is a chatbot. What separates an agent from a single-turn LLM call is the loop: observe the environment, reason about what to do, act, observe the result, and decide whether to continue. The loop structure determines everything – how the agent plans, how it recovers from errors, when it stops, and whether it can handle tasks that take minutes or hours.