One limit changes how you answer attachment-dependent questions: the Gmail connector can see attachment metadata, but cannot directly read the attachment's contents. An attached filename is not evidence of what its document says.
Connect the mailbox that contains the work
On Claude web or Desktop, open Customize > Connectors, add Gmail, review the capabilities, and follow Google's authentication prompts. Team and Enterprise users may first need an Owner or Primary Owner to enable the connector. An organization can also restrict sending actions. Connector setup and tool permissions
Open the target conversation in Gmail yourself before the first request. Check the account, subject, sender, and date. That gives you a clear reference when Claude returns a matching thread.
This uses a connected service. The local MCP extension setup is a different route for tools installed on your computer.
Find the evidence before writing the reply
Suppose a fictional supplier's older email says payment is due in 30 days. A newer message says, “The revised terms are attached,” with a file named updated-terms.pdf. You need to acknowledge the revision without accidentally accepting terms you have not read.
Start with a narrow request:
Use my connected Gmail to find the thread with [SUPPLIER ADDRESS],
subject [EXACT SUBJECT], around [DATE RANGE].
First show the matching subject, participants, latest message date,
and source link. If several threads match, ask me which to use.
List the payment terms actually stated in the message bodies,
with the message date and supporting wording. Separately list
attachments mentioned. Do not infer attachment contents from a
filename or from an older message. Do not draft or send yet.
Open the cited thread. Check whether a reply belongs to this exchange or to another order with a similar subject. Then read the newest relevant message in context.
For this example, the available body text supports “the supplier sent a revision.” It does not establish whether payment remains due in 30 days. The older term and the unread revision need to stay separate.
Resolve an attachment gap explicitly
Read the attachment in Gmail or supply a permitted copy through a supported route. Verify that the document belongs to the latest revision before using its contents. If you cannot access it, ask for clarification rather than allowing the draft to fill the gap.
An authored acknowledgment while the terms remain unreviewed could be:
Thanks for sending the revised terms. We will review the attached document before confirming acceptance. Could you identify the changes to the payment schedule?
Use wording that matches your authority and actual next action. Do not say “we will review” if no one has agreed to do that work. For a text-only revision of an email you already have, the email rewrite guide covers tone and request structure.
Approve the exact message you intend to send
After resolving the source question, ask for a draft on the identified thread:
Prepare a reply to [CONFIRMED THREAD]. Do not send yet.
Recipient and CC: [EXACT ADDRESSES].
Approved facts and commitments: [PASTE].
Purpose of this reply: [ENTER].
Show the recipient fields, subject, and complete body for review.
Use only the approved facts. Do not accept new terms, add a deadline,
include an attachment, or promise payment unless I supplied it.
Wait for my separate instruction before a sending action.
Review addresses as well as wording, especially on a thread with several participants. Resolve placeholders and check any quoted terms against the actual document.
Claude asks for approval before send, reply, and forward actions by default; managed-workspace settings can change permitted behavior. Inspect the connector's tool permissions and any approval shown rather than assuming every account has the same configuration. These capabilities were checked in Anthropic's documentation on October 24, 2026. Sending permissions
After you authorize the intended action, open Gmail Sent and inspect the actual message and thread. Keep the reviewed terms in the team's normal record. A message acknowledging receipt should remain an acknowledgment until someone authorized to accept the terms makes that decision.