outlook_send_with_attachments

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

Annotations already declare readOnlyHint=false and destructiveHint=true, so the safety profile is covered. The description adds non-obvious operational context: the >3MB upload-session fallback and the attachments_dir sandboxing that refuses paths outside the configured directory. It does not contradict the annotations.

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?

Three tight sentences that front-load the core action and the size-based fallback before the path constraint. No filler, though the parenthetical directory defaults add some length.

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?

No output schema exists and annotations carry the mutation profile, so the description's job is the operational detail, which it partially delivers. It omits the meaning of is_html/importance defaults and address-list semantics for to/cc/bcc, leaving gaps an agent must guess at.

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% across 9 parameters, so the description must compensate. It does valuable work on attachment_paths (resolution root, default location, out-of-root refusal) and reply_to (reply routing), but leaves to, cc, bcc, body, is_html, and importance entirely undocumented.

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?

States a specific verb+resource ('Send an email with file attachments'), which inherently distinguishes it from outlook_send_message and the draft tools by the attachment capability. It does not explicitly name a sibling alternative, but the resource is unambiguous.

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?

Gives conditional behavior (auto-switches to upload-session for files >3MB) and path-resolution rules that affect correct invocation. However, it never says when to prefer this over outlook_send_message, outlook_create_draft, or outlook_attach_to_draft, leaving alternative selection to inference.

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