Verified 2026-08-05 What was checked, and when — not a guarantee it is still true.
Cowork runs in two different execution lanes, and they disagree about what 'delivering a file' means. In one, writing the file to the workspace location is itself the delivery. In the other, the location delivers nothing and the file only reaches the user if your skill calls a delivery tool — and the session filesystem is discarded when the session ends, so an undelivered file is simply lost. Write the deliverable to a stated path, then present it with whichever delivery tool the session actually offers, and say the path if there is none.
In one lane the workspace location is itself the delivery channel and writing there is enough. In the other it delivers nothing: the file exists only inside a session filesystem that is discarded when the session ends, and the user never sees it. A skill written against the first behaviour loses its deliverables silently in the second — no error, no warning, just nothing.
From binary Can change without a version bump
This is the pattern Anthropic's own bundled skill-authoring guidance uses, phrased as a capability check rather than a fixed tool name. Check what is available at the moment of use — the tool that presents files differs between lanes — and degrade to naming the path rather than failing. Do not hardcode one tool name and assume it exists.
Caveat: Which delivery tools exist in a session is served at spawn time and has changed across releases; the capability check is what makes this durable, not the tool names.
It costs one sentence and it is the only part of your output that survives every lane, every tool-surface change, and a user reading a transcript later. If delivery silently failed, the stated path is the difference between a recoverable result and a lost one.
Caveat: Reasoned from the lane split rather than measured; the cost is one sentence either way.
Committing files onto the user's machine is infrastructure the agent and the user negotiate through folder-connection consent, not something a skill should reach for. No first-party skill names such a tool. Present the file and let the delivery path be decided outside your skill.
From binary Can change without a version bump
The tool that presents files to the user copies what you give it out of the scratch space for you. Copying first and then presenting the copy produces duplicates and obscures which file is the deliverable.
Caveat: Behaviour of the presenting tool is served per session; check that it exists before relying on it.
On the remote lane the filesystem is discarded at session end. On the local lane undelivered files are hidden from the user rather than destroyed, and can in principle be surfaced on a later turn — but a skill should not depend on that difference. Deliver within the turn that produces the file.
Measured Can change without a version bump
Cowork sessions run either on the user's own machine or on remote infrastructure. The lanes differ in where the filesystem lives, whether it survives the session, and how a file reaches the user. Which lane a session uses depends on how it was created and on account configuration, neither of which a skill can control.
Caveat: Lane availability is rolled out per account, so two users running the same skill can be in different lanes.