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Python
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gmail_reply

Sends a reply to the sender of a conversation's last message, optionally as a draft, with attachments or extra recipients; requires confirm=true and checks unclear send status before retrying.

Instructions

Reply to the sender of the last message of a conversation (or of message_index).

Send is never repeated blind: when Gmail's reaction to Send is unclear the mail is looked up in Outbox / Sent; if that cannot tell, the op fails with error 'send_state_unknown' and nothing is re-sent (check gmail.list folder='sent' before any retry). A result may carry verified_in='outbox' | 'sent' when the send was confirmed that way.

Requires confirm=true (outward-facing or destructive).

Input Schema

TableJSON Schema
NameRequiredDescriptionDefault
ccNoAdditional Cc recipients.
toNoAdditional To recipients.
bccNoAdditional Bcc recipients.
bodyNoText written above the quoted message (any Unicode, newlines allowed).
indexNoRow index of the conversation (from gmail.list / gmail.search); omit to use the conversation already open.
queryNoRun this Gmail search first and take `index` from its results.
folderNoOpen this folder/label first and take `index` from it.
confirmNoMust be true: this action is outward-facing or destructive.
draft_onlyNoSave the reply as a draft instead of sending it.
attachmentsNoPaths of files on this computer to attach.
drive_filesNoGoogle Drive files to insert as links: 'name' (found with Drive search) or '/Folder/name' (from My Drive).
message_indexNoAnswer this message of the thread (0 = oldest, numbering of gmail.read) through its own header actions; default: the last message.
expect_subjectNoSafety check: the conversation's subject must contain this text (case-insensitive), otherwise nothing is sent (not_found).

Schema Changelog

Changes observed during successful MCP inspections.

  1. First observedv0.1.0

TDQS

A3.9/5.0
Behavior4/5

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

With no annotations present, the description carries real weight: it discloses idempotency protection for Send, the 'send_state_unknown' failure mode that prevents blind re-sends, and the verified_in='outbox'|'sent' result field. It does not explain what happens when confirm is omitted or how draft_only changes the flow, but the core safety behavior is unusually well documented.

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

Conciseness4/5

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

Three tight sentences, front-loaded with the action, followed by the failure/retry guidance and the confirm requirement. No filler, though the send-safety paragraph could be trimmed slightly without losing meaning.

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

Completeness4/5

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

For a 13-parameter outward-facing mutation with no annotations and no output schema, the description covers the highest-risk gaps: confirmation, idempotency, error code, and result field. Remaining behaviors (draft_only, attachments, expect_subject) are adequately handled by the schema descriptions.

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

Parameters3/5

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

Schema description coverage is 100%, so the 13 parameters are already fully documented; baseline is 3. The description only adds the semantic that message_index defaults to the last message, which is a marginal supplement.

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

Purpose5/5

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

States a specific verb and resource with precise scope: replying to the sender of the last message (or of message_index) of a conversation. This cleanly separates it from gmail_reply_all and gmail_send without needing to open either schema.

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

Usage Guidelines3/5

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

Gives operational context (confirm=true required, check gmail.list folder='sent' before retrying) but never says when to choose this over gmail_reply_all, gmail_forward, or gmail_draft. Routing to sibling tools is left implicit.

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

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