outlook_send_with_attachments

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

Annotations indicate it is not read-only and not destructive. The description adds behavioral context: auto-switching to upload-session for files >3MB and requirement for absolute paths. This goes beyond annotations without contradiction.

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?

The description is two sentences, front-loading the purpose and a key behavior. Every sentence adds value without redundancy.

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?

The description covers the core functionality but omits return value, error handling, and details on parameters like importance or is_html. Given no output schema, more completeness would be needed for a 9-parameter tool.

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 explain parameters. It only clarifies two parameters (attachment_paths and reply_to) out of nine, leaving others like cc, bcc, is_html, and importance undocumented. Insufficient compensation.

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?

The description explicitly states 'Send an email with file attachments', clearly indicating the verb and resource. It also adds a specific detail about auto-switching for large files, making the purpose distinct from siblings like outlook_send_draft.

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 provides some guidelines: attachment paths must be absolute and reply_to routes replies. However, it does not mention when to use this tool over alternatives such as outlook_send_draft or outlook_attach_to_draft, missing an opportunity to guide tool selection.

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