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Friday, September 19, 2025

Working with Contexts – O’Reilly


The next article comes from two weblog posts by Drew Breunig: “How Lengthy Contexts Fail” and “How one can Repair Your Contexts.”

Managing Your Context Is the Key to Profitable Brokers

As frontier mannequin context home windows proceed to develop,1 with many supporting as much as 1 million tokens, I see many excited discussions about how long-context home windows will unlock the brokers of our goals. In spite of everything, with a big sufficient window, you’ll be able to merely throw the whole lot right into a immediate you may want—instruments, paperwork, directions, and extra—and let the mannequin care for the remaining.

Lengthy contexts kneecapped RAG enthusiasm (no want to seek out the perfect doc when you’ll be able to match all of it within the immediate!), enabled MCP hype (join to each software and fashions can do any job!), and fueled enthusiasm for brokers.2

However in actuality, longer contexts don’t generate higher responses. Overloading your context could cause your brokers and functions to fail in shocking methods. Contexts can change into poisoned, distracting, complicated, or conflicting. That is particularly problematic for brokers, which depend on context to assemble data, synthesize findings, and coordinate actions.

Let’s run via the methods contexts can get out of hand, then assessment strategies to mitigate or solely keep away from context fails.

Context Poisoning

Context poisoning is when a hallucination or different error makes it into the context, the place it’s repeatedly referenced.

The DeepMind crew known as out context poisoning within the Gemini 2.5 technical report, which we broke down beforehand. When enjoying Pokémon, the Gemini agent would sometimes hallucinate, poisoning its context:

An particularly egregious type of this subject can happen with “context poisoning”—the place many elements of the context (objectives, abstract) are “poisoned” with misinformation concerning the sport state, which may usually take a really very long time to undo. In consequence, the mannequin can change into fixated on reaching inconceivable or irrelevant objectives.

If the “objectives” part of its context was poisoned, the agent would develop nonsensical methods and repeat behaviors in pursuit of a purpose that can not be met.

Context Distraction

Context distraction is when a context grows so lengthy that the mannequin over-focuses on the context, neglecting what it discovered throughout coaching.

As context grows throughout an agentic workflow—because the mannequin gathers extra data and builds up historical past—this accrued context can change into distracting moderately than useful. The Pokémon-playing Gemini agent demonstrated this downside clearly:

Whereas Gemini 2.5 Professional helps 1M+ token context, making efficient use of it for brokers presents a brand new analysis frontier. On this agentic setup, it was noticed that because the context grew considerably past 100k tokens, the agent confirmed an inclination towards favoring repeating actions from its huge historical past moderately than synthesizing novel plans. This phenomenon, albeit anecdotal, highlights an necessary distinction between long-context for retrieval and long-context for multistep, generative reasoning.

As an alternative of utilizing its coaching to develop new methods, the agent turned fixated on repeating previous actions from its intensive context historical past.

For smaller fashions, the distraction ceiling is way decrease. A Databricks research discovered that mannequin correctness started to fall round 32k for Llama 3.1-405b and earlier for smaller fashions.

If fashions begin to misbehave lengthy earlier than their context home windows are stuffed, what’s the purpose of tremendous giant context home windows? In a nutshell: summarization3 and truth retrieval. In case you’re not doing both of these, be cautious of your chosen mannequin’s distraction ceiling.

Context Confusion

Context confusion is when superfluous content material within the context is utilized by the mannequin to generate a low-quality response.

For a minute there, it actually appeared like everybody was going to ship an MCP. The dream of a robust mannequin, linked to all your providers and stuff, doing all of your mundane duties felt inside attain. Simply throw all of the software descriptions into the immediate and hit go. Claude’s system immediate confirmed us the way in which, because it’s largely software definitions or directions for utilizing instruments.

However even when consolidation and competitors don’t sluggish MCPscontext confusion will. It turns on the market may be such a factor as too many instruments.

The Berkeley Operate-Calling Leaderboard is a tool-use benchmark that evaluates the power of fashions to successfully use instruments to reply to prompts. Now on its third model, the leaderboard reveals that each mannequin performs worse when supplied with multiple software.4 Additional, the Berkeley crew, “designed eventualities the place not one of the supplied features are related…we anticipate the mannequin’s output to be no perform name.” But, all fashions will sometimes name instruments that aren’t related.

Searching the function-calling leaderboard, you’ll be able to see the issue worsen because the fashions get smaller:

Tool-calling irrelevance score for Gemma models (chart from dbreunig.com, source: Berkeley Function-Calling Leaderboard; created with Datawrapper)

A hanging instance of context confusion may be seen in a latest paper that evaluated small mannequin efficiency on the GeoEngine benchmark, a trial that options 46 totally different instruments. When the crew gave a quantized (compressed) Llama 3.1 8b a question with all 46 instruments, it failed, although the context was effectively inside the 16k context window. However after they solely gave the mannequin 19 instruments, it succeeded.

The issue is, for those who put one thing within the context, the mannequin has to concentrate to it. It might be irrelevant data or unnecessary software definitions, however the mannequin will take it into consideration. Massive fashions, particularly reasoning fashions, are getting higher at ignoring or discarding superfluous context, however we frequently see nugatory data journey up brokers. Longer contexts allow us to stuff in additional information, however this capability comes with downsides.

Context Conflict

Context conflict is if you accrue new data and instruments in your context that conflicts with different data within the context.

This can be a extra problematic model of context confusion. The unhealthy context right here isn’t irrelevant, it straight conflicts with different data within the immediate.

A Microsoft and Salesforce crew documented this brilliantly in a latest paper. The crew took prompts from a number of benchmarks and “sharded” their data throughout a number of prompts. Consider it this manner: Typically, you may sit down and sort paragraphs into ChatGPT or Claude earlier than you hit enter, contemplating each vital element. Different instances, you may begin with a easy immediate, then add additional particulars when the chatbot’s reply isn’t passable. The Microsoft/Salesforce crew modified benchmark prompts to appear like these multistep exchanges:

Microsoft/Salesforce team benchmark prompts

All the knowledge from the immediate on the left facet is contained inside the a number of messages on the proper facet, which might be performed out in a number of chat rounds.

The sharded prompts yielded dramatically worse outcomes, with a median drop of 39%. And the crew examined a variety of fashions—OpenAI’s vaunted o3’s rating dropped from 98.1 to 64.1.

What’s happening? Why are fashions performing worse if data is gathered in levels moderately than ?

The reply is context confusion: The assembled context, containing everything of the chat change, comprises early makes an attempt by the mannequin to reply the problem earlier than it has all the knowledge. These incorrect solutions stay current within the context and affect the mannequin when it generates its ultimate reply. The crew writes:

We discover that LLMs usually make assumptions in early turns and prematurely try to generate ultimate options, on which they overly rely. In easier phrases, we uncover that when LLMs take a incorrect flip in a dialog, they get misplaced and don’t get better.

This doesn’t bode effectively for agent builders. Brokers assemble context from paperwork, software calls, and from different fashions tasked with subproblems. All of this context, pulled from various sources, has the potential to disagree with itself. Additional, if you hook up with MCP instruments you didn’t create there’s a larger probability their descriptions and directions conflict with the remainder of your immediate.

Learnings

The arrival of million-token context home windows felt transformative. The flexibility to throw the whole lot an agent may want into the immediate impressed visions of superintelligent assistants that might entry any doc, join to each software, and preserve good reminiscence.

However, as we’ve seen, greater contexts create new failure modes. Context poisoning embeds errors that compound over time. Context distraction causes brokers to lean closely on their context and repeat previous actions moderately than push ahead. Context confusion results in irrelevant software or doc utilization. Context conflict creates inside contradictions that derail reasoning.

These failures hit brokers hardest as a result of brokers function in precisely the eventualities the place contexts balloon: gathering data from a number of sources, making sequential software calls, partaking in multi-turn reasoning, and accumulating intensive histories.

Luckily, there are answers!

Mitigating and Avoiding Context Failures

Let’s run via the methods we are able to mitigate or keep away from context failures solely.

The whole lot is about data administration. The whole lot within the context influences the response. We’re again to the outdated programming adage of “rubbish in, rubbish out.” Fortunately, there’s loads of choices for coping with the problems above.

RAG

Retrieval-augmented era (RAG) is the act of selectively including related data to assist the LLM generate a greater response.

As a result of a lot has been written about RAG, we’re not going to cowl it right here past saying: It’s very a lot alive.

Each time a mannequin ups the context window ante, a brand new “RAG is useless” debate is born. The final important occasion was when Llama 4 Scout landed with a 10 million token window. At that measurement, it’s actually tempting to suppose, “Screw it, throw all of it in,” and name it a day.

However, as we’ve already lined, for those who deal with your context like a junk drawer, the junk will affect your response. If you wish to study extra, right here’s a new course that appears nice.

Device Loadout

Device loadout is the act of choosing solely related software definitions so as to add to your context.

The time period “loadout” is a gaming time period that refers back to the particular mixture of talents, weapons, and tools you choose earlier than a degree, match, or spherical. Often, your loadout is tailor-made to the context—the character, the extent, the remainder of your crew’s make-up, and your personal talent set. Right here, we’re borrowing the time period to explain choosing essentially the most related instruments for a given job.

Maybe the only solution to choose instruments is to use RAG to your software descriptions. That is precisely what Tiantian Gan and Qiyao Solar did, which they element of their paper “RAG MCP.” By storing their software descriptions in a vector database, they’re capable of choose essentially the most related instruments given an enter immediate.

When prompting DeepSeek-v3, the crew discovered that choosing the proper instruments turns into important when you’ve got greater than 30 instruments. Above 30, the descriptions of the instruments start to overlap, creating confusion. Past 100 instruments, the mannequin was nearly assured to fail their check. Utilizing RAG strategies to pick fewer than 30 instruments yielded dramatically shorter prompts and resulted in as a lot as 3x higher software choice accuracy.

For smaller fashions, the issues start lengthy earlier than we hit 30 instruments. One paper we touched on beforehand, “Much less is Extra,” demonstrated that Llama 3.1 8b fails a benchmark when given 46 instruments, however succeeds when given solely 19 instruments. The problem is context confusion, not context window limitations.

To handle this subject, the crew behind “Much less is Extra” developed a solution to dynamically choose instruments utilizing an LLM-powered software recommender. The LLM was prompted to motive about “quantity and sort of instruments it ‘believes’ it requires to reply the person’s question.” This output was then semantically searched (software RAG, once more) to find out the ultimate loadout. They examined this technique with the Berkeley Operate-Calling Leaderboard, discovering Llama 3.1 8b efficiency improved by 44%.

The “Much less is Extra” paper notes two different advantages to smaller contexts—lowered energy consumption and velocity—essential metrics when working on the edge (which means, operating an LLM in your cellphone or PC, not on a specialised server). Even when their dynamic software choice technique failed to enhance a mannequin’s consequence, the facility financial savings and velocity positive aspects had been well worth the effort, yielding financial savings of 18% and 77%, respectively.

Fortunately, most brokers have smaller floor areas that solely require just a few hand-curated instruments. But when the breadth of features or the quantity of integrations must develop, all the time take into account your loadout.

Context Quarantine

Context quarantine is the act of isolating contexts in their very own devoted threads, every used individually by a number of LLMs.

We see higher outcomes when our contexts aren’t too lengthy and don’t sport irrelevant content material. One solution to obtain that is to interrupt our duties up into smaller, remoted jobs—every with its personal context.

There are many examples of this tactic, however an accessible write-up of this technique is Anthropic’s weblog publish detailing its multi-agent analysis system. They write:

The essence of search is compression: distilling insights from an enormous corpus. Subagents facilitate compression by working in parallel with their very own context home windows, exploring totally different facets of the query concurrently earlier than condensing an important tokens for the lead analysis agent. Every subagent additionally offers separation of issues—distinct instruments, prompts, and exploration trajectories—which reduces path dependency and permits thorough, impartial investigations.

Analysis lends itself to this design sample. When given a query, a number of brokers can determine and individually immediate a number of subquestions or areas of exploration. This not solely hastens the knowledge gathering and distillation (if there’s compute accessible), however it retains every context from accruing an excessive amount of data or data not related to a given immediate, delivering greater high quality outcomes:

Our inside evaluations present that multi-agent analysis programs excel particularly for breadth-first queries that contain pursuing a number of impartial instructions concurrently. We discovered {that a} multi-agent system with Claude Opus 4 because the lead agent and Claude Sonnet 4 subagents outperformed single-agent Claude Opus 4 by 90.2% on our inside analysis eval. For instance, when requested to determine all of the board members of the businesses within the Data Expertise S&P 500, the multi-agent system discovered the proper solutions by decomposing this into duties for subagents, whereas the single-agent system failed to seek out the reply with sluggish, sequential searches.

This strategy additionally helps with software loadouts, because the agent designer can create a number of agent archetypes with their very own devoted loadout and directions for easy methods to make the most of every software.

The problem for agent builders, then, is to seek out alternatives for remoted duties to spin out onto separate threads. Issues that require context-sharing amongst a number of brokers aren’t significantly suited to this tactic.

In case your agent’s area is in any respect suited to parallelization, you’ll want to learn the entire Anthropic write-up. It’s glorious.

Context Pruning

Context pruning is the act of eradicating irrelevant or in any other case unneeded data from the context.

Brokers accrue context as they hearth off instruments and assemble paperwork. At instances, it’s value pausing to evaluate what’s been assembled and take away the cruft. This could possibly be one thing you job your principal LLM with or you may design a separate LLM-powered software to assessment and edit the context. Or you may select one thing extra tailor-made to the pruning job.

Context pruning has a (comparatively) lengthy historical past, as context lengths had been a extra problematic bottleneck within the pure language processing (NLP) subject previous to ChatGPT. Constructing on this historical past, a present pruning technique is Provence, “an environment friendly and strong context pruner for query answering.”

Provence is quick, correct, easy to make use of, and comparatively small—only one.75 GB. You’ll be able to name it in just a few strains, like so:

from transformers import AutoModel

provence = AutoModel.from_pretrained("naver/provence-reranker-debertav3-v1", trust_remote_code=True)

# Learn in a markdown model of the Wikipedia entry for Alameda, CA
with open('alameda_wiki.md', 'r', encoding='utf-8') as f:
    alameda_wiki = f.learn()

# Prune the article, given a query
query = 'What are my choices for leaving Alameda?'
provence_output = provence.course of(query, alameda_wiki)

Provence edited the article, chopping 95% of the content material, leaving me with solely this related subset. It nailed it.

One may make use of Provence or an identical perform to cull paperwork or your entire context. Additional, this sample is a powerful argument for sustaining a structured5 model of your context in a dictionary or different type, from which you assemble a compiled string prior to each LLM name. This construction would come in useful when pruning, permitting you to make sure the principle directions and objectives are preserved whereas the doc or historical past sections may be pruned or summarized.

Context Summarization

Context summarization is the act of boiling down an accrued context right into a condensed abstract.

Context summarization first appeared as a software for coping with smaller context home windows. As your chat session got here near exceeding the utmost context size, a abstract could be generated and a brand new thread would start. Chatbot customers did this manually in ChatGPT or Claude, asking the bot to generate a brief recap that might then be pasted into a brand new session.

Nevertheless, as context home windows elevated, agent builders found there are advantages to summarization in addition to staying inside the whole context restrict. As we’ve seen, past 100,000 tokens the context turns into distracting and causes the agent to depend on its accrued historical past moderately than coaching. Summarization may help it “begin over” and keep away from repeating context-based actions.

Summarizing your context is simple to do, however exhausting to good for any given agent. Figuring out what data needs to be preserved and detailing that to an LLM-powered compression step is important for agent builders. It’s value breaking out this perform as its personal LLM-powered stage or app, which lets you acquire analysis knowledge that may inform and optimize this job straight.

Context Offloading

Context offloading is the act of storing data outdoors the LLM’s context, often through a software that shops and manages the info.

This could be my favourite tactic, if solely as a result of it’s so easy you don’t consider it can work.

Once more, Anthropic has a great write-up of the method, which particulars their “suppose” software, which is mainly a scratchpad:

With the “suppose” software, we’re giving Claude the power to incorporate a further pondering step—full with its personal designated area—as a part of attending to its ultimate reply… That is significantly useful when performing lengthy chains of software calls or in lengthy multi-step conversations with the person.

I actually admire the analysis and different writing Anthropic publishes, however I’m not a fan of this software’s identify. If this software had been known as scratchpad, you’d know its perform instantly. It’s a spot for the mannequin to jot down down notes that don’t cloud its context and can be found for later reference. The identify “suppose” clashes with “prolonged pondering” and needlessly anthropomorphizes the mannequin… however I digress.

Having an area to log notes and progress works. Anthropic reveals pairing the “suppose” software with a domain-specific immediate (which you’d do anyway in an agent) yields important positive aspects: as much as a 54% enchancment in opposition to a benchmark for specialised brokers.

Anthropic recognized three eventualities the place the context offloading sample is beneficial:

  1. Device output evaluation. When Claude must rigorously course of the output of earlier software calls earlier than performing and may must backtrack in its strategy;
  2. Coverage-heavy environments. When Claude must comply with detailed pointers and confirm compliance; and
  3. Sequential resolution making. When every motion builds on earlier ones and errors are expensive (usually present in multi-step domains).

Takeaways

Context administration is often the toughest a part of constructing an agent. Programming the LLM to, as Karpathy says, “pack the context home windows excellent,” neatly deploying instruments, data, and common context upkeep, is the job of the agent designer.

The important thing perception throughout all of the above ways is that context is just not free. Each token within the context influences the mannequin’s habits, for higher or worse. The huge context home windows of contemporary LLMs are a robust functionality, however they’re not an excuse to be sloppy with data administration.

As you construct your subsequent agent or optimize an current one, ask your self: Is the whole lot on this context incomes its hold? If not, you now have six methods to repair it.


Footnotes

  1. Gemini 2.5 and GPT-4.1 have 1 million token context home windows, giant sufficient to throw Infinite Jest in there with loads of room to spare.
  2. The “Lengthy type textual content” part within the Gemini docs sum up this optmism properly.
  3. In truth, within the Databricks research cited above, a frequent method fashions would fail when given lengthy contexts is that they’d return summarizations of the supplied context whereas ignoring any directions contained inside the immediate.
  4. In case you’re on the leaderboard, take note of the “Dwell (AST)” columns. These metrics use real-world software definitions contributed to the product by enterprise, “avoiding the drawbacks of dataset contamination and biased benchmarks.”
  5. Hell, this whole listing of ways is a powerful argument for why it’s best to program your contexts.

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