Sundeep Teki
  • Home
    • About Me
  • AI
    • Consulting
    • Hiring
    • Speaking
    • Papers
    • Testimonials
    • Content
    • Course
    • Neuroscience >
      • Speech
      • Time
      • Memory
  • Coaching
    • Advice
    • Testimonials
  • Training
    • Testimonials
  • Blog
  • Contact
    • News
    • Media

Context Engineering: A Framework for Robust Generative AI Systems

26/6/2025

Comments

 
Picture
Source: https://www.dbreunig.com/2025/06/25/prompts-vs-context.html
Table of Contents (last revised: 14 July, 2025)

1. Conceptual Foundations: From Prompt to System
  • 1.1. Defining the Paradigm: The Rise of Context Engineering
  • 1.2. The "Context is King" Paradigm: Why World-Class Models Underperform
  • 1.3. The "Context-as-a-Compiler" Analogy: A New Mental Model for Development
  • 1.4. Deterministic vs. Probabilistic Context

2. The Architectural Blueprint of Context-Aware Systems
  • 2.1. The Foundational Pattern: Retrieval-Augmented Generation (RAG)
  • 2.2. The Critical Decision: RAG vs. Fine-Tuning
  • 2.3. The Hybrid Approach: The Best of Both Worlds
  • 2.4. The Tech Stack for Context Engineering

3. Advanced Context Engineering Techniques 
  • 3.1. Write: Contextual Memory Architectures
  • 3.2. Select: Advanced Retrieval and Filtering
  • 3.3. Compress: Managing Million-Token Windows
  • 3.4 Isolate: Compartmentalizing Context

4. Advanced Frontiers and State-of-the-Art Techniques (2025)
  • 4.1. The Agentic Leap: From Static Pipelines to Autonomous Systems
  • 4.2. Taming the Beast: Context Compression and Filtering in Million-Token Windows
  • 4.3. Beyond Text: Graph RAG and Structured Knowledge

5. Practical Implementation and Performance
  • 5.1. Context Engineering in the Wild: Industry Use Cases
  • 5.2. Measuring What Matters: A Hybrid Benchmarking Framework
  • 5.3. Best Practices for Production-Grade Context Pipelines

6. Failures of Context
​
7. Resources


Follow-up blog post: From Vibe Coding to Context Engineering

In this guide, I synthesize insights from foundational blog posts on the emergence of Context Engineering, the seminal Lewis et al. paper on Retrieval-Augmented Generation (RAG), and a vast corpus of recent (2024-2025) research on advanced topics like Agentic RAG, Context Compression and the "Context-as-a-Compiler" mental model.

Context Engineering is not an extension of prompt engineering but a distinct system-level discipline focused on creating dynamic, state-aware information ecosystems for AI agents. The key conclusion is that the frontier of AI application development has shifted from model-centric optimization to context-centric architecture design. The most capable models underperform not due to inherent flaws, but because they are provided with an incomplete, "half-baked view of the world".

This guide provides the architectural blueprints, advanced techniques, and practical frameworks necessary to master this critical new discipline.
Picture
Source: https://www.philschmid.de/context-engineering
1. Conceptual Foundations: From Prompt to System
The discourse surrounding Large Language Models (LLMs) has historically been dominated by model scale and prompt design. However, as the capabilities of foundational models begin to plateau, the critical differentiator for building effective, reliable, and "magical" AI applications has shifted from the model itself to the information ecosystem in which it operates. This section establishes the fundamental paradigm shift from the tactical act of writing prompts to the strategic discipline of engineering context, grounding the practitioner in the core principles that motivate this evolution.

1.1. Defining the Paradigm: The Rise of Context Engineering
Context Engineering is the discipline of designing, building, and optimizing the dynamic information ecosystem provided to an AI model to perform a task. It represents a fundamental evolution from the stateless, single-turn world of prompt engineering to the stateful, multi-turn environment of sophisticated AI systems. While prompt engineering focuses on crafting the perfect instruction, context engineering architects the entire world of knowledge the model needs to interpret that instruction correctly and act upon it effectively.

This engineered context is a composite of multiple information streams, including but not limited to:

  • Instructions: The system prompt that defines the LLM's persona, rules, and high-level objectives.
  • User Input: The immediate query or task from the user.
  • Memory: This includes both short-term memory, such as the history of the current dialogue, and long-term memory, like stored user preferences or facts learned in previous sessions.
  • Retrieved Knowledge: Documents and data retrieved from external knowledge bases via Retrieval-Augmented Generation (RAG) to ground the model in factual, up-to-date, or proprietary information.
  • Tool Definitions and Outputs: Schemas describing available external tools (e.g., APIs for weather, stock prices, or internal databases) and the data returned from their execution.
  • Output Constraints: Instructions that specify the desired format of the output, such as a JSON schema or a specific structured layout.
  • Agentic State: For autonomous agents, this includes the current plan, intermediate "thoughts" or reasoning steps stored in a scratchpad, and the overall state of the task workflow.
The central argument is that "context is king" and serves as the primary differentiator between a fragile demo and a robust, production-grade AI product. The distinction between these two disciplines is not merely semantic; it reflects a deep architectural and philosophical shift in how AI applications are conceived and built.

1.2. The "Context is King" Paradigm: Why World-Class Models Underperform
A persistent and uncomfortable truth in applied AI is that the quality of the underlying model is often secondary to the quality of the context it receives. Many teams invest enormous resources in swapping out one state-of-the-art LLM for another, only to see marginal improvements. The reason is that even the most powerful models fail when they are fed an incomplete or inaccurate view of the world.

The core limitation of LLMs is their reliance on parametric knowledge - the information encoded in their weights during training. This knowledge is inherently static, non-attributable, and lacks access to private, real-time, or domain-specific information. When a model is asked a question that requires information beyond its training cut-off date or about a proprietary enterprise database, it is forced to either refuse the query or, more dangerously, "hallucinate" a plausible-sounding but incorrect answer.

Context Engineering directly addresses this fundamental gap. It is the mechanism for providing the necessary grounding to ensure factual accuracy, relevance, and personalization.

Consider a simple task: scheduling an email. A prompt like "Email Jim and find a time to meet next week" sent to a generic LLM will yield a generic, unhelpful draft. However, a system built with context engineering principles would first construct a "contextual snapshot". This snapshot would include:
  • The user's calendar availability.
  • The user's typical meeting preferences (e.g., mornings, 30-minute slots).
  • The history of interactions with "Jim."
  • The user's preferred tone ("be concise, decisive, warm").

By feeding this rich context to the same LLM, the system can generate a "magical" and immediately useful output, such as: "Hey Jim! Tomorrow's packed on my end, back-to-back all day. Thursday AM free if that works for you? Sent an invite, lmk if it works". The model did not get "smarter"; its environment did. This illustrates the core principle: the value is unlocked not by changing the model, but by fixing the context.

1.3. The "Context-as-a-Compiler" Analogy: A New Mental Model for Development
A powerful mental model for understanding this new paradigm is the "Context-as-a-Compiler" analogy, a concept discussed by leading researchers like Andrej Karpathy. This model reframes the LLM as a new kind of compiler that translates a high-level, often ambiguous language (human intent expressed in natural language) into a low-level, executable output (e.g., code, API calls, structured JSON).

In this analogy, the prompt is not just a question; it is the source code. The context is everything else the compiler needs to produce a correct, non-hallucinated binary. This includes the equivalent of:
  • Libraries and Dependencies: Retrieved documents and knowledge sources.
  • Type Definitions and Interfaces: API schemas and tool descriptions.
  • Environmental Variables: User state and real-time system information.

The goal of context engineering, therefore, is to make the compilation process as deterministic and reliable as possible. A traditional C++ compiler will fail if a function is called without being declared; similarly, an LLM will "hallucinate" if it is asked to operate on information it does not have. Context engineering is the practice of providing all the necessary declarations and definitions within the context window to constrain the LLM's stochastic nature and guide it toward the correct output.

This analogy also illuminates a fundamental shift in the developer workflow. When code generated by a tool like GitHub Copilot is wrong, developers often do not debug the incorrect Python code directly. Instead, they "fiddle with the prompt" or adjust the surrounding code until the generation is correct. In the compiler analogy, this is equivalent to modifying the source code and its dependencies. The context is the new debuggable surface. This implies that the primary skill for the AI-native developer is not just writing the final artifact (the code) but curating and structuring the context that generates it. The development environment of the future may evolve into a "context IDE," where developers spend more time managing data sources, retrieval strategies, and agentic workflows than editing lines of code. The rise of "vibe coding" - describing the "vibe" of what is needed and letting the AI handle the implementation - is a direct consequence of this new layer of abstraction.

However, the analogy has its limits. Unlike a traditional compiler, which is a deterministic tool, an LLM is a stochastic system that can creatively resolve ambiguity. This is both its greatest strength and its most significant weakness. While a compiler will throw an error for ambiguous code, an LLM will make its best guess, which can lead to unexpected (and sometimes brilliant, sometimes disastrous) results. The art of context engineering lies in providing enough structure to ensure reliability while leaving just enough room for the model's powerful generative capabilities to shine.

1.4 Deterministic vs. Probabilistic Context
A crucial distinction within context engineering is between deterministic and probabilistic context.

  • Deterministic Context refers to all static, controlled, and predictable inputs provided to the LLM. This includes the system prompt, user-uploaded documents, few-shot examples, and hard-coded rules or instructions. Most traditional prompt engineering techniques are focused on optimizing this deterministic portion of the context for clarity, efficiency, and cost (e.g., token usage).
 
  • Probabilistic Context encompasses all dynamic, external, and inherently uncertain information sources that the LLM can access. This primarily includes results from web searches or queries against large, evolving internal databases. When an agent is given access to the internet, this probabilistic context can overwhelm the deterministic inputs due to its sheer volume and variability.

The introduction of probabilistic context presents significant engineering challenges. The quality, reliability, and factuality of the information are not guaranteed. It dramatically increases the system's vulnerability to security risks, such as LLM injection attacks, where malicious content retrieved from an external source can manipulate the model's behavior. Furthermore, traditional evaluation metrics like precision and recall become less effective, as the "correct" context is not known a priori. Engineering robust systems therefore requires a focus on shaping the agent's exploration of this probabilistic space, monitoring the quality of information sources, and implementing rigorous security precautions.
2. The Architectural Blueprint of Context-Aware Systems
Moving from conceptual foundations to technical implementation, this section details the architectural patterns and components that form the backbone of modern context-engineered systems. These blueprints provide the "how" that enables the "why" discussed previously, focusing on the core mechanisms for grounding LLMs in external knowledge.

2.1. The Foundational Pattern: Retrieval-Augmented Generation (RAG)
Retrieval-Augmented Generation (RAG) is the cornerstone pattern of context engineering. Introduced in the seminal 2020 paper by Lewis et al., RAG was designed to combine the strengths of parametric memory (knowledge stored in model weights) and non-parametric memory (an external knowledge base). 

RAG was proposed as a general-purpose recipe to address these issues by combining the implicit, parametric memory of a pre-trained model with an explicit, non-parametric memory in the form of a retrievable text corpus. The core innovation was to treat the retrieved document as a latent variable, enabling the retriever and generator components to be trained jointly, end-to-end.

While LLMs demonstrated a remarkable ability to internalize knowledge from their training data, they suffered from several critical flaws:
  • Knowledge Staleness: Their knowledge was frozen at the time of training, making them unable to access up-to-date information.
  • Lack of Provenance: They could not cite their sources, making it impossible to verify their claims.
  • Hallucination: They were prone to fabricating facts with high confidence.
  • Difficult Updates: Expanding or revising their knowledge base required costly and complex retraining.

The standard RAG process consists of three primary stages :
  1. Ingestion & Chunking: The first step is to load data from its source, which can range from PDFs and text files to websites and API endpoints. Because LLMs have a finite context window and embedding models have input size limits, this raw data must be broken down into smaller, semantically meaningful "chunks." The chunking strategy is a critical tuning parameter; chunks that are too small may lack sufficient context, while chunks that are too large can introduce noise. Common strategies include fixed-size chunking with overlap or more sophisticated methods like sentence-aware splitting.

  2. Indexing & Embedding: Each text chunk is then processed by an embedding model (e.g., sentence-transformers/all-MiniLM-l6-v2 or more advanced proprietary models). This model converts the text into a high-dimensional dense vector - an embedding—that numerically represents its semantic meaning. These vectors, along with the original text chunks and any associated metadata, are then loaded into a specialized vector database for efficient storage and retrieval.
    ​

  3. Retrieval & Augmentation: When a user submits a query, the application first embeds the query using the same embedding model. It then uses this query vector to search the vector database, typically using an Approximate Nearest Neighbor (ANN) search algorithm to find the top-k document chunks whose embeddings are most similar (e.g., by cosine similarity or dot product) to the query embedding. These top-k retrieved chunks are then formatted and prepended to the user's original query and the system prompt. This combined text forms the final, augmented context that is passed to the LLM for generation.

This entire pipeline serves as the fundamental mechanism for context engineering, providing a structured way to inject relevant, external knowledge into the LLM's reasoning process at inference time.

2.2. The Critical Decision: RAG vs. Fine-Tuning
A primary strategic decision facing any team building with LLMs is whether to use RAG, fine-tuning, or both. These methods address different problems and have distinct trade-offs in terms of cost, complexity, and capability. Choosing the correct path is crucial for project success.

  • RAG is fundamentally about providing knowledge. It excels when an application must operate on external, dynamic, or proprietary information. Its key strengths are providing up-to-date responses, reducing factual hallucinations by grounding outputs in source material, and offering explainability by citing sources. Implementation is generally less complex and cheaper than fine-tuning, as it primarily involves data pipelines and architecture rather than GPU-intensive training runs.

  • Fine-tuning is fundamentally about teaching a skill or behavior. It modifies the model's weights to adapt its style, tone, or format, or to make it an expert in a highly specialized domain with its own jargon and reasoning patterns. It is best for embedding static knowledge that is required consistently across many tasks, or for altering the fundamental way the model responds.

The consensus among practitioners is to start with RAG by default. It is faster, cheaper, and safer for most use cases involving factual knowledge. Fine-tuning should only be considered when RAG proves insufficient to achieve the desired behavior or when the task is purely about style and not knowledge.
Picture
A decision matrix to guide the choice of RAG vs. Fine-tuning vs. Hybrid systems
2.3. The Hybrid Approach: The Best of Both Worlds
While RAG and fine-tuning are often presented as an either/or choice, the most sophisticated systems frequently employ a hybrid approach to achieve performance that neither method can reach in isolation. This strategy recognizes that the two methods are complementary: RAG provides the facts, while fine-tuning teaches the skill of using those facts.

The standard RAG approach relies on a general-purpose base model to synthesize an answer from the retrieved context. However, this base model may not be optimized for this specific task. It might struggle to identify the most salient points in the context, ignore contradictory evidence, or fail to structure the output in the desired format.

A hybrid approach addresses this by fine-tuning the generator model specifically to be a better RAG component. The fine-tuning dataset in this case would not consist of just questions and answers. Instead, each example would be a triplet of (query, retrieved_context, ideal_answer). The goal of this fine-tuning is not to bake the knowledge from the retrieved_context into the model's weights. Rather, it is to teach the model the skill of faithfully synthesizing a high-quality answer from whatever context it is given.

This fine-tuning can teach the model to:
  • Pay closer attention to the provided context and ignore its own parametric knowledge.
  • Handle noisy or irrelevant retrieved documents more gracefully.
  • Adhere to a specific output format (e.g., "Answer the question and then provide a list of supporting quotes from the context").
  • Synthesize information from multiple retrieved chunks.

​The optimal architecture for many complex enterprise applications is therefore a model that has been fine-tuned for "contextual reasoning and synthesis," coupled with a powerful and dynamic RAG pipeline. This allows the system to learn the desired style and structure via fine-tuning, while dynamically populating its responses with up-to-date facts from RAG.

2.4 The Tech Stack for Context Engineering

Building production-grade, context-aware systems relies on a maturing ecosystem of specialized tools and frameworks. Mastering this tech stack is as important as understanding the conceptual architecture.
​
  • Vector Stores:
    These are specialized databases designed for efficient storage and querying of high-dimensional vector embeddings. They are the backbone of any RAG system. Prominent examples include open-source libraries like
    FAISS (developed by Meta) and pgvector (an extension for PostgreSQL), as well as managed cloud services like Pinecone and Weaviate. These systems use ANN algorithms to perform similarity searches over billions of vectors with low latency.


  • Orchestration Frameworks:
    These are libraries that provide abstractions and tools to simplify the development of complex LLM applications, often referred to as "chains" or "graphs." They handle the plumbing of connecting LLMs to data sources, managing state, and sequencing operations. The two dominant frameworks are
    LangChain and LlamaIndex. They provide pre-built components for data loading, chunking, retrieval, and agent creation. More recently, frameworks like LangGraph have emerged to specifically address the need for building stateful, cyclic, multi-agent applications, which are difficult to represent as a simple linear chain.


  • Memory Layers:
    For applications requiring statefulness, such as chatbots or long-running agents, dedicated memory layers are essential. These can be simple in-memory buffers for short-term dialogue history or more sophisticated systems that integrate with vector stores to provide long-term, persistent memory of user preferences or past interactions. These layers often include logic for managing memory size, such as summarization or implementing Time-to-Live (TTL) policies.

    ​
  • Summarization & Transformation Pipelines:
    As context windows grow, the need to compress and structure information becomes paramount. This has led to the development of dedicated pipelines, often using smaller, faster, and fine-tuned LLMs, to perform tasks like summarizing retrieved documents, extracting key entities, or transforming raw text into a structured JSON format before it is passed to the main reasoning model.
Picture
3. Advanced Context Engineering Techniques

As LLM applications move from simple prototypes to robust production systems, developers quickly discover that a naive RAG implementation is often insufficient. The quality of an LLM's output is exquisitely sensitive to the quality of its context. Therefore, a significant portion of engineering effort is dedicated to advanced techniques for curating this context. These strategies can be grouped into four core patterns: writing, selecting, compressing, and isolating information.

3.1 Write: Contextual Memory Architectures
LLMs are inherently stateless; they have no memory of past interactions beyond what is explicitly provided in the current context window. Building coherent, multi-turn applications requires architecting an external memory system. This is the "Write" pattern: saving state and learned information for future reference.

  • Short-Term Memory: This typically refers to the history of the current conversation. Managing it is a balancing act between providing sufficient context for coherence and avoiding context window overflow. Simple strategies include a "sliding window" that only keeps the last N turns. More advanced techniques involve using a smaller LLM to summarize the conversation history periodically or using embedding-based retrieval to pull only the most relevant past messages into the current context, rather than the entire log.

  • Long-Term Memory: This is designed to persist information across sessions, such as user preferences, key facts, or relationship histories. This is almost universally implemented as a retrieval problem. When a user states a preference (e.g., "I am a vegan"), that fact is embedded and stored in a dedicated vector database. In subsequent interactions, the system can retrieve these facts to personalize its responses, effectively giving the LLM a persistent memory.

  • Scratchpads: This is a form of working memory crucial for agentic workflows. As an agent decomposes a complex problem, it can "write down" its plan, intermediate results, or observations into a temporary storage space (a "scratchpad"). It can then "read" from this scratchpad in subsequent steps, allowing it to execute long, multi-step reasoning chains without losing its train of thought due to context window limitations.

3.2 Select: Advanced Retrieval and Filtering
The "Select" pattern focuses on improving the signal-to-noise ratio of the information retrieved for the context window. The goal is to move beyond naive vector similarity and retrieve documents that are not just semantically similar but truly useful for answering the user's query.

  • Query Transformations: The user's raw query is often not the optimal query for a retrieval system. Advanced RAG pipelines often transform the query first. Techniques include using an LLM to break a single complex question into multiple, more specific sub-queries, or generating a "hypothetical answer" to the query and then using the embedding of that hypothetical answer for retrieval, which can often find more relevant documents.

  • Hybrid Search: Relying solely on dense (vector) retrieval can sometimes fail, especially for queries containing specific keywords, codes, or rare terms. Hybrid search mitigates this by combining dense retrieval with a traditional sparse retrieval algorithm like BM25 (a keyword-based method). The final ranking is a weighted combination of the scores from both systems, providing the benefits of both semantic understanding and keyword matching.
 
  • Re-ranking: A common and highly effective technique is to use a two-stage retrieval process. The first stage uses a fast but less accurate retriever (like a vector search or BM25) to fetch a large set of candidate documents (e.g., the top 100). The second stage then uses a more powerful but computationally expensive model, typically a cross-encoder, to re-rank these candidates. A cross-encoder processes the query and a document together, allowing for much deeper interaction and a more accurate relevance judgment. This ensures the final documents passed to the LLM are of the highest possible relevance.

3.3 Compress: Managing Million-Token Windows
The advent of million-token context windows did not eliminate the need for context engineering; paradoxically, it intensified it. A larger window is not a bigger brain but a bigger, noisier room that requires a more sophisticated librarian. Research has consistently shown that LLMs suffer from a "lost in the middle" problem, where their ability to recall information is highest at the beginning and end of the context window and significantly degrades for information buried in the middle.11 Furthermore, processing long contexts is computationally expensive and slow. This makes naive context-stuffing both ineffective and inefficient. The most advanced systems recognize that architecture trumps raw context size; a well-designed RAG system with a smaller, curated context can outperform a naive system with a million-token window. The "Compress" pattern is therefore critical for managing these large contexts effectively.

  • Context Summarization: This involves using an LLM to generate a concise summary of long documents or conversation histories before they are added to the context. For extremely long inputs, this can be done recursively: summarizing chunks, then summarizing the summaries, and so on.

  • Context Pruning: This is an extractive approach that intelligently removes less relevant sentences or chunks from the context. This can be heuristic-based (e.g., always dropping the oldest messages in a chat history) or model-based. For example, the Provence model is a lightweight transformer trained specifically to identify and "prune" sentences from retrieved documents that are unlikely to be useful for answering a given query, reducing noise without losing key information.

  • Structured Extraction: Instead of passing raw, unstructured text to the main LLM, a pre-processing step can use a smaller LLM to extract the key information into a highly token-efficient structured format like JSON. This not only saves tokens but also makes the information easier for the main model to parse and use reliably.

3.4 Isolate: Compartmentalizing Context
Mixing unrelated information streams into a single context window - a "context soup" - is a recipe for failure. It can lead to several distinct problems:

  • Context Distraction: Irrelevant information distracts the model from the primary task.
  • Context Confusion: The model struggles to follow the main thread of reasoning.
  • Context Clash: Contradictory information from different sources confuses the model, leading to inconsistent or hedged answers.
​
The "Isolate" pattern addresses this by strictly compartmentalizing context. Different tasks, sub-agents, or conversational threads should operate within their own isolated context windows. This is typically managed by the orchestration layer. Frameworks like LangGraph, for example, are designed around a central state object. For each independent workflow or session, a separate state object is maintained. The logic of the graph ensures that at any given step, only the relevant parts of that state (e.g., the current sub-task's instructions, the relevant memory) are passed into the LLM's context, preventing interference from other, unrelated processes.
4. Advanced Frontiers and State-of-the-Art Techniques (2025)
The field of Context Engineering is evolving at a breathtaking pace. Beyond the foundational RAG pattern, a new frontier of autonomous, efficient, and structured techniques is emerging. This section explores the state-of-the-art developments that are defining production-grade AI systems in 2025 and beyond.

41. The Agentic Leap: From Static Pipelines to Autonomous Systems
The most significant evolution in context engineering is the shift from linear RAG pipelines to dynamic, autonomous systems known as Agentic RAG. While traditional RAG follows a fixed Retrieve -> Augment -> Generate sequence, Agentic RAG embeds this process within a reasoning loop run by an autonomous agent. This transforms the system from a simple information processor into an adaptive problem-solver.

Agentic RAG systems are built upon a set of core design patterns that enable autonomous behavior :
  • Planning: The agent first breaks down a complex, multi-step user query into a sequence of smaller, executable tasks. For example, the query "Compare the Q1 financial performance of our company with our top two competitors" might be decomposed into: (1) Identify our company's top two competitors, (2) Find our company's Q1 earnings report, (3) Find competitor A's Q1 report, (4) Find competitor B's Q1 report, (5) Synthesize the key metrics and generate a comparison table.
  • Tool Use: Agents are given access to a suite of external tools, which can range from simple web search APIs to complex code interpreters or internal database query engines. The agent's planning step determines which tools to use and in what order to gather the necessary information.
  • Reflection: After executing a step or generating a piece of information, the agent can pause to self-critique its output. It might ask itself: "Is this answer complete? Does it directly address the user's query? Is the source reliable?" This reflective loop allows for iterative refinement and error correction, leading to a much higher quality final response.
  • Multi-Agent Collaboration: For highly complex workflows, a single agent may be insufficient. Multi-agent systems distribute responsibilities across a team of specialized agents. For instance, a "Manager" agent might perform the initial planning and delegate sub-tasks to a "Web Search" agent, a "Database" agent, and a "Summarization" agent. These agents collaborate to fulfill the request, passing information back and forth before the final answer is composed.
This evolution from static to agentic systems represents a significant leap in capability, enabling applications to handle ambiguity, perform multi-hop reasoning, and interact with the world in a far more sophisticated manner.

4.2. Taming the Beast: Context Compression and Filtering in Million-Token Windows
As LLMs with context windows of one million tokens or more become commonplace, a new set of challenges has emerged. While vast context windows are powerful, they introduce significant issues with cost, latency, and the "needle-in-a-haystack" problem, where models struggle to identify and use relevant information buried within a sea of irrelevant text. Simply stuffing more documents into the prompt is not a viable strategy.
The solution lies in intelligent context compression and filtering. The state-of-the-art in this area has moved beyond simple summarization to more sophisticated, query-aware techniques.

A leading example is the 
Sentinel framework, proposed in May 2025. Sentinel offers a lightweight yet highly effective method for compressing retrieved context before it is passed to the main LLM.


The core mechanism of Sentinel is both clever and efficient :
  1. Reframing the Problem: Instead of training a large, dedicated model to perform compression (which is expensive and not portable), Sentinel reframes compression as an attention-based understanding task.
  2. Using a Proxy Model: It takes a small, off-the-shelf "proxy" LLM (e.g., a 0.5B parameter model). The retrieved documents and the user query are fed into this small model.
  3. Probing Attention: Sentinel does not care about the text the proxy model generates. Instead, it probes the internal decoder attention scores. Specifically, it looks at the attention patterns from the final generated token back to the input sentences. The hypothesis, which holds up empirically, is that sentences highly relevant to the query will receive more attention from the model as it prepares to generate an answer.
  4. Lightweight Classification: These attention signals are extracted as feature vectors for each sentence. A very simple, lightweight classifier (a logistic regression model) is trained to map these attention features to a relevance score.
  5. Filtering: At inference time, sentences are scored for relevance using this proxy model and classifier. Only the top-scoring sentences are selected and passed to the large, expensive generator LLM.

The key advantage of Sentinel is its efficiency and portability. The central finding is that query-context relevance signals are remarkably consistent across different model scales. This means a tiny 0.5B model can act as an effective proxy for a massive 70B model in determining what context is important. On the LongBench benchmark, Sentinel can achieve up to 5x context compression while matching the question-answering performance of systems that use the full, uncompressed context, and it outperforms much larger and more complex compression models.

4.3. Beyond Text: Graph RAG and Structured Knowledge
The majority of RAG implementations operate on unstructured text. However, a great deal of high-value enterprise knowledge is structured, residing in databases or knowledge graphs. Graph RAG is an emerging frontier that integrates these structured knowledge sources into the retrieval process.

Instead of retrieving disconnected chunks of text, Graph RAG traverses a knowledge graph to retrieve interconnected entities and their relationships. This allows the system to perform complex, multi-hop reasoning that would be nearly impossible with text-based retrieval alone. For example, to answer "Which customers in Germany are using a product that relies on a component from a supplier who recently had a security breach?", a Graph RAG system could traverse the graph from the breached supplier to the affected components, to the products using those components, and finally to the customers who have purchased those products in Germany.

This approach enriches the context provided to the LLM with a structured understanding of how different pieces of information relate to one another, unlocking a more profound level of reasoning and analysis.
5. Practical Implementation and Performance
Bringing these advanced concepts into production requires a focus on real-world applications, robust measurement, and disciplined engineering practices. This final section of the technical guide provides a pragmatic roadmap for implementing, benchmarking, and maintaining high-performance, context-aware systems.

5.1. Context Engineering in the Wild: Industry Use Cases
Context engineering is not a theoretical exercise; it is the driving force behind a new generation of AI applications across numerous industries.
  • Developer Platforms & Agentic Coding: The next evolution of coding assistants is moving beyond simple autocomplete. Systems are being built that have full context of an entire codebase, integrating with Language Server Protocols (LSP) to understand type errors, parsing production logs to identify bugs, and reading recent commits to maintain coding style. These agentic systems can autonomously write code, create pull requests, and even debug issues based on a rich, real-time understanding of the development environment.
  • Enterprise Knowledge Federation: Enterprises struggle with knowledge fragmented across countless silos: Confluence, Jira, SharePoint, Slack, CRMs, and various databases. Context engineering provides the architecture to unify these disparate sources. An enterprise AI assistant can use a multi-agent RAG system to query a Confluence page, pull a ticket status from Jira, and retrieve customer data from a CRM to answer a complex query, presenting a single, unified, and trustworthy response.
  • Hyper-Personalization: In sectors like e-commerce, healthcare, and finance, deep context is enabling unprecedented levels of personalization. A financial advisor bot can provide tailored advice by accessing a user's entire portfolio, their stated risk tolerance, and real-time market data. A healthcare assistant can offer more accurate guidance by considering a patient's full medical history, recent lab results, and even data from wearable devices.

5.2. Measuring What Matters: A Hybrid Benchmarking Framework
To build and maintain high-performing systems, one must measure what matters. However, teams often fall into the trap of focusing on a narrow set of metrics. An AI team might obsess over RAG evaluation scores (like faithfulness and relevance) while ignoring a slow and brittle deployment pipeline. Conversely, a platform engineering team might optimize for DORA metrics like cycle time while deploying a model that frequently hallucinates.

The performance of a context-aware system is a function of both its AI quality and the engineering velocity that supports it. A truly elite team must track both. This requires a unified "Context Engineering Balanced Scorecard" that bridges the worlds of MLOps and DevOps, providing a holistic view of system health and performance.

The logic is straightforward: a model with perfect accuracy is useless if it takes three months to deploy an update. A system with daily deployments is a liability if each deployment introduces new factual errors. Success requires excellence on both fronts.

​
Evaluating complex, multi-component RAG and agentic systems is a critical challenge. A single accuracy score is meaningless. A robust evaluation framework must be multi-faceted, assessing the performance of each component individually and the system as a whole.

Component-Level Metrics:
Retrieval Quality: The performance of the retriever is the foundation of the entire system. Key metrics include:
  • Context Precision/Relevance: Of the documents that were retrieved, what fraction are actually relevant to the query?
  • Context Recall: Of all the relevant documents that exist in the knowledge base, what fraction did the retriever find?
  • Standard information retrieval metrics like Mean Reciprocal Rank (MRR) and Mean Average Precision (MAP) are often used to quantify this performance.

Generation Quality: The generator's output must be evaluated against the retrieved context. Key metrics include:
  • Faithfulness / Groundedness: Does the generated answer strictly adhere to the information present in the provided context? This measures the absence of hallucination.
  • Answer Relevance: Does the answer directly and completely address the user's question? A faithful answer can still be irrelevant if it uses the context to answer the wrong question.

LLM-as-a-Judge:
Given the nuance and scale required for evaluation, a popular technique is to use a powerful LLM (like GPT-4o) as an automated evaluator. The "judge" LLM is given the query, the retrieved context, and the generated answer, along with a rubric of criteria (e.g., "Rate the faithfulness of this answer on a scale of 1-5"). This allows for scalable, qualitative assessment.


5.3. Best Practices for Production-Grade Context Pipelines
Distilling insights from across the research and practitioner landscape, a set of clear best practices emerges for building robust, production-grade context engineering systems.

  • Treat Context as a Product: Your knowledge base is not a static asset; it is a living product. Implement version control, automated quality checks, monitoring for data drift, and feedback loops to continuously improve the quality of your context sources.

  • Structure and Isolate with Precision: Use clear, consistent formatting and delimiters (e.g., XML tags) to separate instructions, retrieved context, and the user query. This helps the model parse the input reliably. In multi-agent or multi-task systems, rigorously isolate the context for each workflow to prevent interference and context clash.

  • Start with RAG, Fine-Tune Sparingly: Default to RAG for injecting external or dynamic knowledge. It is generally cheaper, faster to implement, and easier to maintain and update. Reserve the significant investment of fine-tuning for cases where the goal is to teach the model a specific skill, style, or implicit reasoning pattern that cannot be easily conveyed through retrieved text.

  • Iterate, Evaluate, and Experiment Relentlessly: Building an effective context pipeline is an empirical science. It requires relentless iteration and experimentation with different chunking strategies, retrieval algorithms, re-rankers, and prompt templates. A/B testing different context configurations and measuring their impact on end-to-end quality metrics is crucial for optimization.
    ​
  • Embrace Linguistic Compression: Especially in the system prompt and other deterministic parts of the context, every token counts. Use precise, unambiguous language to maximize information density. A well-structured prompt with clear rules can guide the model's behavior more effectively and token-efficiently than a verbose, conversational one.
6. Failures of Context

For a deeper dive into the various failure modes of context understanding, I recommend Drew Breunig's excellent blog in which he highlights 4 diverse challenges of long context - 

  • Context Poisoning: When a hallucination or other error makes it into the context, where it is repeatedly referenced.
  • Context Distraction: When a context grows so long that the model over-focuses on the context, neglecting what it learned during training.
  • Context Confusion: When superfluous information in the context is used by the model to generate a low-quality response.
  • Context Clash: When you accrue new information and tools in your context that conflicts with other information in the prompt.

He also shares potential solutions to effective context management - 
  • RAG: Selectively adding relevant information to help the LLM generate a better response
  • Tool Loadout: Selecting only relevant tool definitions to add to your context
  • Context Quarantine: Isolating contexts in their own dedicated threads
  • Context Pruning: Removing irrelevant or otherwise unneeded information from the context
  • Context Summarization: Boiling down an accrued context into a condensed summary
  • Context Offloading: Storing information outside the LLM's context, usually via a tool that stores and manages the data
7. Resources
  • https://blog.langchain.com/the-rise-of-context-engineering/ 
  • https://www.dbreunig.com/2025/06/26/how-to-fix-your-context.html
  • https://www.dbreunig.com/2025/06/22/how-contexts-fail-and-how-to-fix-them.html
  • https://boristane.com/blog/context-engineering/ 
  • https://x.com/karpathy/status/1937902205765607626
  • Context Engineering is the New Vibe Coding - https://www.youtube.com/watch?v=Egeuql3Lrzg
  • Lewis et al. (2020), "Retrieval-Augmented Generation for Knowledge-Intensive NLP Tasks"
  • Singh et al. (2025), "Agentic Retrieval-Augmented Generation: A Survey"
  • Zhang et al. (2025), "Sentinel: Attention Probing."
Comments
comments powered by Disqus

    Archives

    July 2025
    June 2025
    May 2025
    April 2025
    March 2025
    February 2025
    January 2025
    October 2024
    September 2024
    March 2024
    February 2024
    April 2023
    December 2022
    November 2022
    October 2022
    September 2022
    August 2022
    July 2022
    June 2022
    May 2022
    April 2022
    March 2022
    February 2022
    December 2021
    October 2021
    August 2021
    May 2021
    April 2021
    March 2021

    Categories

    All
    Ai
    Data
    Education
    Genai
    India
    Jobs
    Leadership
    NLP
    RemoteWork
    Science
    Speech
    Strategy
    Web3

    RSS Feed


    Copyright © 2025, Sundeep Teki
    All rights reserved. No part of these articles may be reproduced, distributed, or transmitted in any form or by any means, including  electronic or mechanical methods, without the prior written permission of the author. 
    Disclaimer
    This is a personal blog. Any views or opinions represented in this blog are personal and belong solely to the blog owner and do not represent those of people, institutions or organizations that the owner may or may not be associated with in professional or personal capacity, unless explicitly stated.
                                                                                                                                                                                 [email protected] 
​​  ​© 2025 | Sundeep Teki
  • Home
    • About Me
  • AI
    • Consulting
    • Hiring
    • Speaking
    • Papers
    • Testimonials
    • Content
    • Course
    • Neuroscience >
      • Speech
      • Time
      • Memory
  • Coaching
    • Advice
    • Testimonials
  • Training
    • Testimonials
  • Blog
  • Contact
    • News
    • Media