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Connectors: what they actually read and write
A connector's capabilities are checked service by service: as recorded on 2 September 2026, the Google Workspace Gmail connector can send, reply to and forward messages directly, with approval requested by default before each send, which on a Team or Enterprise plan an organisation owner can allow members to lift, while the Microsoft 365 connector for Outlook can also send, but only once an administrator of the account has switched on that capability for the whole organisation.
A connector's capabilities should never be guessed by resemblance to another tool from the same vendor. As recorded on 2 September 2026, the Google Workspace Gmail connector can send, reply to and forward messages directly.
An approval by default, revocable under condition
By default, Cowork asks for approval before each of these three sends. On a Team or Enterprise account, it is the account's administrators who decide whether members can let these actions run without asking for confirmation each time.
Cowork : envoyer ce message a fournisseur@exemple.fr ?
Approbation requise par defaut avant chaque envoi
The word shown on screen is the same, send, but the switch that authorises it is not in the same place depending on which mail service is used.
Two switches, two different locations
The Microsoft 365 connector for Outlook can also send a message, update a calendar or create a file, but this capability depends on what an administrator of the account has switched on across the whole organisation. An account connected before these writing functions arrived stays blocked until an administrator has gone through the activation steps required.
On a Team or Enterprise plan, an organisation owner decides whether members have the right to lift this approval; outside these plans, the documentation describes no way to remove it. Outlook places the activation switch on the administrator's side of the account, off by default. Checking which of the two applies before promising an automatic send avoids announcing a capability that is not yet open. In both cases, as long as the default setting has not been changed, the proposed action stays displayed before it goes out, which leaves one last chance to reread the recipient and the content of the message.
What still needs checking before promising a send
A connector capability documented today can change tomorrow with no visible warning in the interface. Before telling a colleague or a member that a send will go out automatically, opening the documentation for the exact connector being used, not that of a neighbouring connector from the same vendor, avoids promising a capability that does not yet exist or that has just changed without anyone noticing.
The rule that does not change
This check has to be redone for each connector taken separately, a calendar, a storage space, an internal messaging tool: see what Cowork can touch for the full map of the access plans a connector sits within.
Gmail and Outlook, two different send switches
| Connector | Reading | Writing, draft and send |
|---|---|---|
| Gmail, Google Workspace connector | Yes | Yes, direct send as recorded on 2 September 2026, with approval by default revocable by members on an owner's decision, Team and Enterprise plans |
| Outlook, Microsoft 365 connector | Yes | Sending possible, switched on only by an administrator of the account for the whole organisation |
A secretary connects the Google Workspace Gmail connector to Cowork and asks it to reply to a supplier to confirm an order. Cowork drafts the reply and shows an approval request before sending. The secretary closes her computer to go on her lunch break.
Write one sentence stating what this situation establishes, and one sentence stating what it does not establish.
What this establishes: It establishes that a reply draft was produced and that approval was requested before the message was actually sent.
What this does not establish: It does not establish whether the message actually went out, nor whether the secretary's account is set to ask for this approval every time or has already lifted it.
The three most common miscalibrations
- Trop large It establishes that any message drafted by the Gmail connector always waits for approval before going out, whatever the account setting.
- Trop étroit It establishes only that the secretary left for her lunch break, without saying anything about the reply drafted by Cowork.
- À côté It establishes that the Microsoft 365 connector for Outlook works under the same approval rules as Gmail.
- The Google Workspace Gmail connector can today send, reply to and forward messages directly, to be checked on your own connector before promising it to a third party.
- By default Cowork asks for approval before each Gmail send; on a Team or Enterprise plan, an owner can allow members to lift this setting.
- The Microsoft 365 connector for Outlook can also send a message, provided an administrator of the account has switched on this capability for the whole organisation.
- Checking which exact connector is at stake, not the vendor or the service in general, avoids announcing a sending capability that is not yet activated.
Open the settings of the Gmail connector linked to your Cowork, and check whether approval before each send is still switched on or whether it has already been lifted for your account or your organisation.
Every datable claim in this lesson links here to the public text behind it. A source that does not open proves nothing.
- Anthropic, using Google Workspace connectors, direct send from Gmail consultée le 2026-09-02
- Anthropic, connecting to Microsoft 365, write actions subject to the administrator consultée le 2026-09-02