outlook_send_with_attachments

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

The description discloses an important behavioral trait: auto-switching to upload-session for files >3MB. With no annotations provided, this adds value. However, it does not cover other behavioral aspects such as error handling, rate limits, authentication requirements, or the nature of the operation (write).

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 very concise: two sentences and a code block. Every sentence adds value, and the most critical information (purpose, large-file handling, path constraint) is front-loaded.

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 tool has 9 parameters, 4 required, and no output schema. The description provides only partial parameter guidance and does not describe return values, error scenarios, or any side effects. Given the complexity, the description is insufficient for an agent to use the tool correctly without additional information.

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. It adds meaningful context for 'attachment_paths' (must be absolute paths) and 'reply_to' (route replies). However, it does not explain the other 7 parameters (to, subject, body, cc, bcc, is_html, importance) beyond what the schema titles provide.

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 clearly states the tool sends an email with file attachments, and adds specific behavioral context (auto-switch for large files). The name 'send_with_attachments' distinguishes it from siblings like 'outlook_send_message' or '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 mentions that attachment_paths must be absolute paths and reply_to is for routing replies, providing some usage guidance. However, it does not explicitly instruct when to use this tool over alternatives like 'outlook_send_message' or 'outlook_send_draft', nor does it specify prerequisites or exclusions.

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