Context Management Is the Hardest Problem in Agent Systems
February 11, 2026
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Context management might be the single most important unsolved problem in agent systems.
Not because people aren’t trying.
They are.
The solutions just aren’t good enough.
If you’ve built with agents for more than a week, you’ve felt this.
That fleeting moment where everything works.
The agent has exactly the right context.
It understands the goal.
It’s making steady progress.
The agent has exactly the right context.
It understands the goal.
It’s making steady progress.
It feels like magic.
And then… it doesn’t.
The Illusion of “Just Add Memory”
One common approach is global memory.
Give the agent a long-term store.
Let it write things down.
Let it recall them later.
Let it write things down.
Let it recall them later.
In theory, this creates continuity.
In practice?
You spend your days pruning the mountains of garbage your agent decided were important.
Half-formed plans.
Redundant notes.
Misinterpretations.
Artifacts from directions you abandoned hours ago.
Redundant notes.
Misinterpretations.
Artifacts from directions you abandoned hours ago.
The agent remembers everything.
Including the things it absolutely should forget.
Plans in Text Files (and Other Coping Mechanisms)
Another approach: external plans.
Write the strategy into a text file.
Keep the agent aligned.
Force it to follow structure.
Keep the agent aligned.
Force it to follow structure.
This works—until it doesn’t.
Because the moment reality shifts and the agent needs to change course, the old plan lingers.
Fragments of outdated logic remain.
Assumptions that are no longer true keep influencing decisions.
The past quietly poisons the future.
And Then There’s Summarization
Summarization is the devil.
You’re working with an agent toward a solution.
You’re iterating.
Fixing mistakes.
Refining direction.
You’re iterating.
Fixing mistakes.
Refining direction.
You feel momentum building.
Then the context window fills up.
So the system summarizes.
And in doing so, it quietly deletes the very nuance that made the progress possible.
Suddenly the agent:
- Forgets constraints you clarified
- Reintroduces bugs you already fixed
- Walks straight into problems you just solved
It’s like watching it step on every rake you already stepped on.
Except now you’re just standing there.
Watching.
The Core Tension
Agents are powerful when they hold the right context.
But most current approaches force humans to become context managers.
You’re not just solving the problem.
You’re:
- Editing memory
- Cleaning summaries
- Rewriting plans
- Nudging direction
At some point, it feels like you’re servicing the model as much as it’s helping you.
And that’s backwards.
The promise of agents is leverage.
The reality, today, is babysitting.
The Feeling We’re Chasing
Every once in a while, everything clicks.
The agent understands the goal.
It retains the important details.
It adapts when conditions change.
It builds on prior progress without dragging old mistakes forward.
It retains the important details.
It adapts when conditions change.
It builds on prior progress without dragging old mistakes forward.
That’s the magic.
The moment when it feels like you’re collaborating—not supervising.
At Structify, that’s the feeling we chase for our customers.
We’ve made long strides in making queries feel effortless.
In making systems feel like they understand business context.
In making systems feel like they understand business context.
But context management itself—true, adaptive, intelligent context handling—remains one of the most important frontiers in agent design.
Because until agents can manage context gracefully…
They won’t feel like teammates.
They’ll feel like interns with short-term memory loss.
And the moment we solve that?
That’s when agent systems really change how we work.
