Boomerang Task Orchestration Hides Context, and That Confuses Users

Context tokens: 47,832.

Context tokens: 0.

You didn't clear anything. The orchestrator spawned a subtask.

The disappearing context

You're debugging a flaky integration test. You ask Roo Code to investigate, and the orchestrator does what orchestrators do: it plans, then delegates. "I'm going to break this into steps," it says. Boom. It jumps into architect mode.

Architect mode starts fresh. Your context counter resets to zero. The 47k tokens of conversation history, the stack traces you pasted, the file references you built up - gone from the subtask's perspective.

If you're watching closely, you can see a new task was spawned. But the visual signal is easy to miss. The subtask runs in isolation from its parent. This is intentional. Subtasks need focused context to do their job without inheriting noise from the parent conversation.

The problem: it looks like something broke.

"One of the things we've really noticed is that it's not always clear what's going on in the task orchestration process. You start a task, it says, 'Okay, I'm going to plan this out.' Boom. It jumps into architect mode. Architect mode's doing its thing. Now, your context is back at zero."

Hannes Rudolph, Office Hours S01E08

The isolation is a feature

Subtask isolation exists for a reason. When an orchestrator delegates work, each subtask needs a clean context window. If subtasks inherited the full parent context, they'd burn tokens on irrelevant history and drift toward the parent's framing instead of their narrow assignment.

The architecture is sound. The visibility is not.

When you watch a subtask spin up, you lose the thread. You can't easily see: what was the parent's intent? What context did this subtask receive? How does this subtask's token spend contribute to the total task cost?

"If you're paying really close attention to the process, you can see that a new task was spawned. And so, the new task stands alone from the parent task. And this is sort of confusing."

Hannes Rudolph, Office Hours S01E08

Recovery is manual

When something fails mid-subtask, the recovery path is clunky. You cancel, restore to a checkpoint, and re-prompt. There's no "resume from parent with different subtask parameters." The orchestrator doesn't expose the delegation decisions in a way that lets you tweak one branch without starting over.

For teams that use orchestration heavily, this compounds. Five subtasks deep, you've lost track of which branch failed and why. The parent task shows completion, but one subtask quietly errored. Costs accumulated across the chain, but you can't see the breakdown until you audit the token logs.

The roadmap reality

The team knows this needs work. But orchestration visibility competes with other priorities.

"I think the possibility of expanding the workflow is good, but we still have a lot of stuff that can be reprioritized first. It is definitely something that we look forward to. It's just that the prep work that needs to be done to get there is quite a lot."

Ellie, Office Hours S01E08

Translation: orchestration improvements are coming, but not tomorrow. The infrastructure work required to surface parent-child relationships, cost breakdowns, and resumable branches is substantial.

Why this matters for your team

For a Series A-to-C engineering team running orchestrated workflows alongside daily shipping, the visibility gap hurts in two places.

First, debugging. When a subtask fails and you can't trace what context it received or what the parent's intent was, you're guessing at the failure mode instead of diagnosing it.

Second, cost governance. If you're tracking token spend at the org level, you need to know: did that expensive task run because of a legitimate complexity, or because the orchestrator spawned redundant subtasks that repeated work?

The current workaround: watch the task panel closely, note when subtasks spawn, and manually track which branches are active. It's not elegant, but it's the reality until the tooling catches up.

What to do now

If your team uses orchestration heavily, set expectations. The isolation behavior is intentional, and it won't change. What will improve over time is the visibility into that isolation.

In the meantime: audit your task logs periodically. Look for patterns where subtasks spawn unexpectedly or costs spike without clear cause. Flag those cases to the team. The feedback loop between user friction and roadmap prioritization is real.

The context counter resetting isn't a bug. But the confusion it causes is a design debt that the team is actively tracking.

How Roo Code closes the loop on orchestration

Roo Code's orchestrator mode enables complex multi-step workflows by delegating specialized subtasks to focused modes like architect, code, or debug. This close-the-loop architecture lets the agent plan, execute, run tests, and iterate based on results without requiring you to manually coordinate each step.

With BYOK (bring your own key), you maintain direct control over token spend while the orchestrator manages task decomposition. Each subtask runs with intentional context isolation, ensuring focused execution without inheriting noise from parent conversations.

Roo Code's orchestrator spawns isolated subtasks to prevent context pollution and enable focused execution, though visibility into parent-child relationships and aggregated token costs remains an area of active development.

Orchestration approaches compared