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Cherami

Reply to email

reply_message
Destructive

Reply to a message, with recipients and subject derived from it. Derived recipients come from sender-written headers: check them against the assignment. To choose recipients yourself, use send_message with in_reply_to.

Input Schema

NameRequiredDescriptionDefault
htmlNoOptional HTML alternative to your response.
textYesYour response; original history is not automatically quoted.
labelsNo
inbox_idYesInbox to send from; it must hold the source message.
message_idYesReady received or accepted sent message in this inbox. A reply to received mail goes to its Reply-To, or From when there is none; a reply to sent mail goes to its original To.
attachmentsNoNew files for this reply; original attachments are not copied.
idempotency_keyNoMakes a retry safe: repeating the call with the same key and identical arguments within 24 hours of the first request returns the original attempt instead of sending again. Use a new key for each intended email.

Output Schema

NameRequiredDescriptionDefault

No arguments

Schema Changelog

Changes observed during successful MCP inspections.

  1. Changed4 schema fields changed
    • changedInput schema / properties / idempotency_key / description
      Previous value: -"Use a unique key per intended email. Retain the key, exact payload and first request time; reuse only for that attempt within 24 hours, even if the source is later deleted."New value: +"Makes a retry safe: repeating the call with the same key and identical arguments within 24 hours of the first request returns the original attempt instead of sending again. Use a new key for each intended email."
    • changedInput schema / properties / inbox_id / description
      Previous value: -"Sending inbox; must own the source message."New value: +"Inbox to send from; it must hold the source message."
    • changedInput schema / properties / message_id / description
      Previous value: -"Ready received or accepted sent message in this inbox. Received replies use Reply-To, otherwise From; sent replies use original To. Reply-all also includes visible To/Cc."New value: +"Ready received or accepted sent message in this inbox. A reply to received mail goes to its Reply-To, or From when there is none; a reply to sent mail goes to its original To."
    • changedOutput schema / anyOf
      Previous value: -[
      -  {
      -    "additionalProperties": false,
      -    "properties": {
      -      "idempotency_expires_at": {
      -        "description": "End of retry-key protection. Retrying an uncertain send after this instant can send it again.",
      -        "type": "string"
      -      },
      -      "limited": {
      -        "const": false,
      -        "type": "boolean"
      -      },
      -      "message": {
      -        "anyOf": [
      -          {
      -            "additionalProperties": false,
      -            "properties": {
      -              "created_at": {
      -                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      -                "type": "string"
      -              },
      -              "error_code": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "id": {
      -                "type": "string"
      -              },
      -              "in_reply_to": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "inbox_id": {
      -                "type": "string"
      -              },
      -              "labels": {
      -                "items": {
      -                  "type": "string"
      -                },
      -                "type": "array"
      -              },
      -              "recipient_count": {
      -                "maximum": 9007199254740991,
      -                "minimum": 0,
      -                "type": "integer"
      -              },
      -              "status": {
      -                "const": "accepted",
      -                "description": "Accepted by the email provider, not confirmation of delivery.",
      -                "type": "string"
      -              },
      -              "thread_id": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              }
      -            },
      -            "required": [
      -              "id",
      -              "inbox_id",
      -              "thread_id",
      -              "created_at",
      -              "recipient_count",
      -              "error_code",
      -              "in_reply_to",
      -              "labels",
      -              "status"
      -            ],
      -            "type": "object"
      -          },
      -          {
      -            "additionalProperties": false,
      -            "properties": {
      -              "created_at": {
      -                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      -                "type": "string"
      -              },
      -              "error_code": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "guidance": {
      -                "type": "string"
      -              },
      -              "id": {
      -                "type": "string"
      -              },
      -              "in_reply_to": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "inbox_id": {
      -                "type": "string"
      -              },
      -              "labels": {
      -                "items": {
      -                  "type": "string"
      -                },
      -                "type": "array"
      -              },
      -              "recipient_count": {
      -                "maximum": 9007199254740991,
      -                "minimum": 0,
      -                "type": "integer"
      -              },
      -              "status": {
      -                "enum": [
      -                  "rejected",
      -                  "unknown"
      -                ],
      -                "type": "string"
      -              },
      -              "thread_id": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              }
      -            },
      -            "required": [
      -              "id",
      -              "inbox_id",
      -              "thread_id",
      -              "created_at",
      -              "recipient_count",
      -              "error_code",
      -              "in_reply_to",
      -              "labels",
      -              "status",
      -              "guidance"
      -            ],
      -            "type": "object"
      -          }
      -        ]
      -      },
      -      "outcome_persisted": {
      -        "const": true,
      -        "type": "boolean"
      -      },
      -      "replayed": {
      -        "type": "boolean"
      -      }
      -    },
      -    "required": [
      -      "limited",
      -      "message",
      -      "outcome_persisted"
      -    ],
      -    "type": "object"
      -  },
      -  {
      -    "additionalProperties": false,
      -    "properties": {
      -      "guidance": {
      -        "type": "string"
      -      },
      -      "idempotency_expires_at": {
      -        "description": "End of retry-key protection. Retrying an uncertain send after this instant can send it again.",
      -        "type": "string"
      -      },
      -      "limited": {
      -        "const": false,
      -        "type": "boolean"
      -      },
      -      "message": {
      -        "anyOf": [
      -          {
      -            "additionalProperties": false,
      -            "properties": {
      -              "created_at": {
      -                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      -                "type": "string"
      -              },
      -              "error_code": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "id": {
      -                "type": "string"
      -              },
      -              "in_reply_to": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "inbox_id": {
      -                "type": "string"
      -              },
      -              "labels": {
      -                "items": {
      -                  "type": "string"
      -                },
      -                "type": "array"
      -              },
      -              "recipient_count": {
      -                "maximum": 9007199254740991,
      -                "minimum": 0,
      -                "type": "integer"
      -              },
      -              "status": {
      -                "const": "accepted",
      -                "description": "Accepted by the email provider, not confirmation of delivery.",
      -                "type": "string"
      -              },
      -              "thread_id": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              }
      -            },
      -            "required": [
      -              "id",
      -              "inbox_id",
      -              "thread_id",
      -              "created_at",
      -              "recipient_count",
      -              "error_code",
      -              "in_reply_to",
      -              "labels",
      -              "status"
      -            ],
      -            "type": "object"
      -          },
      -          {
      -            "additionalProperties": false,
      -            "properties": {
      -              "created_at": {
      -                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      -                "type": "string"
      -              },
      -              "error_code": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "guidance": {
      -                "type": "string"
      -              },
      -              "id": {
      -                "type": "string"
      -              },
      -              "in_reply_to": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              },
      -              "inbox_id": {
      -                "type": "string"
      -              },
      -              "labels": {
      -                "items": {
      -                  "type": "string"
      -                },
      -                "type": "array"
      -              },
      -              "recipient_count": {
      -                "maximum": 9007199254740991,
      -                "minimum": 0,
      -                "type": "integer"
      -              },
      -              "status": {
      -                "enum": [
      -                  "rejected",
      -                  "unknown"
      -                ],
      -                "type": "string"
      -              },
      -              "thread_id": {
      -                "type": [
      -                  "string",
      -                  "null"
      -                ]
      -              }
      -            },
      -            "required": [
      -              "id",
      -              "inbox_id",
      -              "thread_id",
      -              "created_at",
      -              "recipient_count",
      -              "error_code",
      -              "in_reply_to",
      -              "labels",
      -              "status",
      -              "guidance"
      -            ],
      -            "type": "object"
      -          }
      -        ]
      -      },
      -      "outcome_persisted": {
      -        "const": false,
      -        "type": "boolean"
      -      },
      -      "replayed": {
      -        "type": "boolean"
      -      }
      -    },
      -    "required": [
      -      "limited",
      -      "message",
      -      "outcome_persisted",
      -      "guidance"
      -    ],
      -    "type": "object"
      -  }
      -]New value: +[
      +  {
      +    "additionalProperties": false,
      +    "properties": {
      +      "idempotency_expires_at": {
      +        "description": "Until this time, a retry with the same idempotency_key returns this send; after it, the same key sends again.",
      +        "type": "string"
      +      },
      +      "limited": {
      +        "const": false,
      +        "type": "boolean"
      +      },
      +      "message": {
      +        "anyOf": [
      +          {
      +            "additionalProperties": false,
      +            "properties": {
      +              "created_at": {
      +                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      +                "type": "string"
      +              },
      +              "error_code": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "id": {
      +                "type": "string"
      +              },
      +              "in_reply_to": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "inbox_id": {
      +                "type": "string"
      +              },
      +              "labels": {
      +                "items": {
      +                  "type": "string"
      +                },
      +                "type": "array"
      +              },
      +              "recipient_count": {
      +                "maximum": 9007199254740991,
      +                "minimum": 0,
      +                "type": "integer"
      +              },
      +              "status": {
      +                "const": "accepted",
      +                "description": "Accepted by the email provider, not confirmation of delivery.",
      +                "type": "string"
      +              },
      +              "thread_id": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              }
      +            },
      +            "required": [
      +              "id",
      +              "inbox_id",
      +              "thread_id",
      +              "created_at",
      +              "recipient_count",
      +              "error_code",
      +              "in_reply_to",
      +              "labels",
      +              "status"
      +            ],
      +            "type": "object"
      +          },
      +          {
      +            "additionalProperties": false,
      +            "properties": {
      +              "created_at": {
      +                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      +                "type": "string"
      +              },
      +              "error_code": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "guidance": {
      +                "type": "string"
      +              },
      +              "id": {
      +                "type": "string"
      +              },
      +              "in_reply_to": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "inbox_id": {
      +                "type": "string"
      +              },
      +              "labels": {
      +                "items": {
      +                  "type": "string"
      +                },
      +                "type": "array"
      +              },
      +              "recipient_count": {
      +                "maximum": 9007199254740991,
      +                "minimum": 0,
      +                "type": "integer"
      +              },
      +              "status": {
      +                "enum": [
      +                  "rejected",
      +                  "unknown"
      +                ],
      +                "type": "string"
      +              },
      +              "thread_id": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              }
      +            },
      +            "required": [
      +              "id",
      +              "inbox_id",
      +              "thread_id",
      +              "created_at",
      +              "recipient_count",
      +              "error_code",
      +              "in_reply_to",
      +              "labels",
      +              "status",
      +              "guidance"
      +            ],
      +            "type": "object"
      +          }
      +        ],
      +        "description": "The saved send. Check status: a successful call can still return rejected or unknown."
      +      },
      +      "outcome_persisted": {
      +        "const": true,
      +        "type": "boolean"
      +      },
      +      "replayed": {
      +        "type": "boolean"
      +      }
      +    },
      +    "required": [
      +      "limited",
      +      "message",
      +      "outcome_persisted"
      +    ],
      +    "type": "object"
      +  },
      +  {
      +    "additionalProperties": false,
      +    "properties": {
      +      "guidance": {
      +        "type": "string"
      +      },
      +      "idempotency_expires_at": {
      +        "description": "Until this time, a retry with the same idempotency_key returns this send; after it, the same key sends again.",
      +        "type": "string"
      +      },
      +      "limited": {
      +        "const": false,
      +        "type": "boolean"
      +      },
      +      "message": {
      +        "anyOf": [
      +          {
      +            "additionalProperties": false,
      +            "properties": {
      +              "created_at": {
      +                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      +                "type": "string"
      +              },
      +              "error_code": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "id": {
      +                "type": "string"
      +              },
      +              "in_reply_to": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "inbox_id": {
      +                "type": "string"
      +              },
      +              "labels": {
      +                "items": {
      +                  "type": "string"
      +                },
      +                "type": "array"
      +              },
      +              "recipient_count": {
      +                "maximum": 9007199254740991,
      +                "minimum": 0,
      +                "type": "integer"
      +              },
      +              "status": {
      +                "const": "accepted",
      +                "description": "Accepted by the email provider, not confirmation of delivery.",
      +                "type": "string"
      +              },
      +              "thread_id": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              }
      +            },
      +            "required": [
      +              "id",
      +              "inbox_id",
      +              "thread_id",
      +              "created_at",
      +              "recipient_count",
      +              "error_code",
      +              "in_reply_to",
      +              "labels",
      +              "status"
      +            ],
      +            "type": "object"
      +          },
      +          {
      +            "additionalProperties": false,
      +            "properties": {
      +              "created_at": {
      +                "description": "Absolute ISO 8601 service timestamp in UTC (Z), with millisecond precision.",
      +                "type": "string"
      +              },
      +              "error_code": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "guidance": {
      +                "type": "string"
      +              },
      +              "id": {
      +                "type": "string"
      +              },
      +              "in_reply_to": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              },
      +              "inbox_id": {
      +                "type": "string"
      +              },
      +              "labels": {
      +                "items": {
      +                  "type": "string"
      +                },
      +                "type": "array"
      +              },
      +              "recipient_count": {
      +                "maximum": 9007199254740991,
      +                "minimum": 0,
      +                "type": "integer"
      +              },
      +              "status": {
      +                "enum": [
      +                  "rejected",
      +                  "unknown"
      +                ],
      +                "type": "string"
      +              },
      +              "thread_id": {
      +                "type": [
      +                  "string",
      +                  "null"
      +                ]
      +              }
      +            },
      +            "required": [
      +              "id",
      +              "inbox_id",
      +              "thread_id",
      +              "created_at",
      +              "recipient_count",
      +              "error_code",
      +              "in_reply_to",
      +              "labels",
      +              "status",
      +              "guidance"
      +            ],
      +            "type": "object"
      +          }
      +        ],
      +        "description": "The saved send. Check status: a successful call can still return rejected or unknown."
      +      },
      +      "outcome_persisted": {
      +        "const": false,
      +        "type": "boolean"
      +      },
      +      "replayed": {
      +        "type": "boolean"
      +      }
      +    },
      +    "required": [
      +      "limited",
      +      "message",
      +      "outcome_persisted",
      +      "guidance"
      +    ],
      +    "type": "object"
      +  }
      +]
  2. First observed

TDQS

A4/5.0
Behavior4/5

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

Annotations already declare destructive=true and idempotent=false, so the safety profile is covered. The description adds genuine non-obvious context: that recipients are taken from sender-written headers and should be verified before sending, which is a spoofing-relevant warning not present in the structured fields.

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

Conciseness5/5

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

Two sentences with no waste, front-loaded with the core action and then the derivation caveat and the alternative routing. Every clause earns its place.

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?

Output schema exists so return values need no explanation, and annotations cover the safety profile. The description covers the recipient-derivation nuance and the alternative tool; the only gap is that it never mentions the idempotency guarantee, leaving that entirely to the schema.

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 86%, so the schema already documents every parameter in detail (inbox_id, message_id, text, labels, attachments, idempotency_key). The description adds no parameter-level meaning beyond what the schema provides, so the baseline of 3 applies.

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

Purpose4/5

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

States a specific verb and resource ('Reply to a message') plus the key distinguishing behavior: recipients and subject are derived from the source rather than supplied by the caller. It routes away from send_message but does not explicitly distinguish itself from the sibling reply_all_message, which an agent would need to choose correctly.

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

Usage Guidelines4/5

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

Explicitly names the alternative (send_message with in_reply_to) for the case where the caller wants to pick recipients, and warns to check derived recipients against the assignment. It lacks explicit when-not guidance versus reply_all_message, so it falls short of a 5.

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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