9 Best AI Assistants That Work With Gmail and Outlook
The assistants built by the big platforms are anchored to their own identity provider. Gemini is a Google product reading Google data. Microsoft 365 Copilot is a Microsoft product reading Microsoft data. If your work life is in one and your personal life is in the other, which is extremely common, most of the obvious answers cover half your mail.
We checked nine tools in August 2026 against a simple test: can one subscription hold a Gmail or Google Workspace mailbox and an Outlook or Microsoft 365 mailbox at the same time, and what can it do in each.
What separates them
Both at once, or one at a time. A tool that supports Gmail and supports Outlook is not the same as a tool that holds both in one session. If answering a question means disconnecting and reauthorizing, the answer is one at a time.
Read, draft, or send. Reading is table stakes. Drafting is common. Sending real mail from the address that owns the thread is where the list thins out fast.
Asked, or automatic. Almost every assistant here works when you open it. Whether anything happens to a message that arrives while you are asleep is the sharpest dividing line in the category.
1. Carly
The only tool on this list that holds both mailboxes and acts on them without being asked.
Carly is an AI executive assistant that connects to Gmail and Outlook together and runs on triggers, in the cloud. When a message arrives it gets read and handled: triaged, filed, answered, turned into a task, pushed into the CRM. Your laptop does not have to be awake and no chat window has to be open.
It drafts and sends real email, attachments included, from whichever address owns the thread. It covers calendars on both sides. Each agent can have its own email address. And you set it up by describing the outcome in plain English, at which point it interviews you and builds the workflow with you, rather than leaving you to engineer a prompt.
Free Zapier-style workflows; AI agents from $35/month. Start on the integrations page, or see Gmail and Outlook.
Both mailboxes: yes · Sends: yes · Acts on arrival: yes
2. ChatGPT
The strongest of the general assistants at this, by a wide margin.
OpenAI ships Gmail, Google Calendar, Outlook Email and Outlook Calendar as separate apps you connect, on Plus, Pro, Business and Enterprise. The free tier does not include connected apps at all.
Sending is no longer a clean dividing line. ChatGPT sends from either Gmail or Outlook once connected, showing you the draft before it goes. Claude sends through Microsoft 365, off until you enable it, while its Gmail connector remains draft-only.
The Outlook side has gone further than most people realize, reaching shared and delegated mailboxes: reading them, browsing folders, marking mail read or unread, moving messages, and sending plain-text mail on behalf of the mailbox. On a work tenant, admin action controls and Microsoft Entra approval govern what is actually available.
The limit is that each connector holds one account, so two Gmail identities is still a reconnect, and nothing fires on arrival.
Both mailboxes: yes · Sends: yes · Acts on arrival: no
3. Superhuman
The email client answer rather than the chatbot answer, and the one that handles the two-ecosystem problem most gracefully day to day.
Superhuman works with Gmail and with Microsoft, covering personal outlook.com addresses and Microsoft 365 business accounts, and it lets you connect as many of each as you want. Switching between an Outlook account and a Gmail account happens inside the app rather than by signing out of anything. The AI writing, keyboard shortcuts, split inbox and CRM features behave the same on both sides, which is not true of every cross-provider client.
It is a fast interface over your mail with AI woven through it. You are still the one working the inbox.
Both mailboxes: yes · Sends: yes, you send · Acts on arrival: no
4. Claude
Claude reaches both ecosystems, and the sending story is genuinely split down the middle.
Through Google Workspace connectors it reads Gmail and drafts. Through the Microsoft 365 connector it reads Outlook and can actually send, once that is enabled. The result is an assistant where the answer to “can it send my email” depends on which mailbox you mean, which is counterintuitive enough that people get it wrong in both directions.
Like the others in this tier, it works inside a conversation you start.
Both mailboxes: yes · Sends: Outlook yes, Gmail draft only · Acts on arrival: no
5. Microsoft Copilot
The surprise entry, because it is a Microsoft product that reaches into Google.
The consumer Copilot assistant has opt-in connectors for Gmail, Google Calendar, Google Contacts and Google Drive, alongside OneDrive and Outlook.com, available on Copilot.com and on Copilot mobile. Microsoft frames the capability as finding things: asking in natural language and getting the right message back. Drafting and sending from a connected Gmail are not described.
Do not confuse it with Microsoft 365 Copilot, the one your employer buys, which works against your organization’s Microsoft data and does not reach a personal Gmail.
Both mailboxes: yes · Sends: no · Acts on arrival: no
6. Spark Mail
A long-standing multi-account client covering Gmail, Outlook and Exchange, iCloud and generic IMAP, with AI writing and summarizing layered on. Its strength is breadth of provider support rather than depth of automation, which makes it a reasonable pick if your mail is spread across more than two places.
Both mailboxes: yes · Sends: yes, you send · Acts on arrival: no
7. Missive
Built for shared inboxes rather than personal ones, and it connects Gmail, Outlook and Office 365 alongside other channels. If the real problem is a team working one support@ or hello@ address across two providers, this shape fits better than a personal assistant does. The AI features assist the humans in the thread rather than running the thread.
Both mailboxes: yes · Sends: yes, you send · Acts on arrival: rules only
8. Front
The heavier team version of the same idea, connecting Gmail and Outlook plus other channels into shared workflows with routing and assignment. It has genuine automation, though the automation is rule-shaped rather than an assistant deciding what a message needs.
Both mailboxes: yes · Sends: yes, you send · Acts on arrival: rules only
9. Gemini Enterprise
Worth knowing about, because Google’s enterprise product does what the consumer Gemini app does not.
Gemini Enterprise publishes a Microsoft Outlook connector reaching mail, calendars and contacts, with documented actions including send mail, create and update events, create and update contacts, and downloading attachments up to 25 MB. It is an administrator build, requiring an Azure app registration and Microsoft Graph delegated permissions, and it runs in global, US and EU regions.
So Google will absolutely put your Outlook mail in front of Gemini. Just not through anything you can switch on yourself.
Both mailboxes: yes · Sends: yes · Acts on arrival: no · Setup: admin
Which ones did not make it
The Gemini app and Gemini in Gmail. These are Google-account surfaces. The Workspace connection covers Gmail, Docs, Drive, Calendar, Keep, Tasks and Classroom, and there is no Outlook in that list. Details in can Gemini access Outlook.
Shortwave. Built on the Gmail and Google Workspace API, with no Outlook or Microsoft 365 support. Excellent inside Gmail, and irrelevant if half your mail is elsewhere.
The comparison
| Gmail | Outlook | Both at once | Sends | Acts on arrival | |
|---|---|---|---|---|---|
| Carly | Yes | Yes | Yes | Yes | Yes |
| ChatGPT | Yes | Yes | Yes | Yes | No |
| Superhuman | Yes | Yes | Yes | You send | No |
| Claude | Yes | Yes | Yes | Outlook only | No |
| Microsoft Copilot | Search | Yes | Yes | No | No |
| Spark Mail | Yes | Yes | Yes | You send | No |
| Missive | Yes | Yes | Yes | You send | Rules |
| Front | Yes | Yes | Yes | You send | Rules |
| Gemini Enterprise | Yes | Yes | Yes | Yes | No |
| Gemini app | Yes | No | No | No | No |
| Shortwave | Yes | No | No | You send | No |
How to choose
If you want a faster inbox and you are happy to be the one working it, Superhuman is the cleanest cross-provider client here, and Spark is the wider-net version of the same idea.
If you want to ask questions of your mail and occasionally have something sent, ChatGPT covers both ecosystems on a paid plan and does more with Outlook than anything else in its class.
If a team shares an address, Missive or Front are built for that and the personal assistants are not.
And if the goal is that the mail gets handled whether or not you show up, that is a different category of tool. Carly works on triggers across both mailboxes, sends real email with attachments, and gets built by describing what you want rather than by configuring rules. Free Zapier-style workflows; AI agents from $35/month. For per-tenant deployments or programmatic access, book a call.
Frequently Asked Questions
Which AI assistant works with both Gmail and Outlook?
Carly, ChatGPT, Claude, Superhuman, Microsoft Copilot, Spark, Missive and Front all reach both. They differ sharply in what they can do once connected, particularly on sending and on whether anything happens without you asking.
Can Gemini work with Outlook?
Not in the Gemini app or the AI features inside Gmail, which are built around a Google account. Gemini Enterprise has an administrator-configured Microsoft Outlook connector that reaches mail, calendars and contacts.
Does Microsoft 365 Copilot read Gmail?
No. The connectors that reach Gmail belong to the consumer Microsoft Copilot assistant. Microsoft 365 Copilot works against your organization’s Microsoft data.
Which assistants can actually send email, not just draft it?
ChatGPT sends from a connected Gmail or Outlook on paid plans with you confirming each send. Claude sends through Microsoft 365 but stops at a draft in Gmail. Carly sends from either side, with attachments.
What if I have two Gmail accounts as well as Outlook?
Built-in connectors authorize one identity per provider, so a second Gmail usually means disconnecting and reconnecting. See best AI assistants for multiple Gmail accounts.
More: Best AI email assistants · Best AI assistants for multiple email accounts · Can ChatGPT access Outlook? · Can Copilot access Gmail? · Can Gemini access Outlook? · Best AI inbox management tools
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"Before Carly, I relied on a Calendly link, but the whole process felt impersonal and not very professional. Carly changed that by handling all the back-and-forth, so I'm no longer stuck in endless email threads trying to line up schedules.
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