jira_upload_attachment

Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

Annotations only tell the agent this is a non-idempotent, non-destructive write; the description adds substantive context the annotations cannot convey: path allowlist enforcement, '..' traversal and symlink-escape rejection, per-file and per-batch size limits, relative-path resolution against the server working directory, and explicit advice not to retry blindly. That is a rich behavioral profile for a mutation tool.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

Six tight sentences with the WRITE marker and the core action front-loaded; every subsequent sentence carries a distinct constraint (paths, limits, relative resolution, retry policy). No filler or restatement of the name.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

For a two-parameter mutation tool with no output schema, the description covers the risky parts well. It does not say what comes back (attachment IDs/metadata) or what error conditions look like beyond the retry warning, which is the main remaining gap.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema coverage is 0%, so the description must compensate, and it does for filePaths: allowed root, traversal/symlink rules, relative-path base, size limits, and the 1–10 range. issueKey is left to its regex pattern, which is largely self-documenting, but no explicit statement about its format or where to obtain it.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

Opens with an explicit verb and resource ("WRITE: upload 1–10 local files to a Jira issue"), including the batch-size scope. It is trivially distinguishable from the attachment siblings (list, download, cleanup) and from issue/comment writers.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

The description gives operational constraints (allowlist, no blind retries) but never states when to use this versus jira_download_attachment or jira_list_attachments, nor any prerequisite like issue permissions. Usage is implied by the verb rather than spelled out.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.