Best AI Assistants for Google Workspace and Microsoft 365
Your day job is on Microsoft 365. The rest of your life is on Google. Two inboxes, two calendars, two places your files live.
Every assistant built into a suite is a citizen of that suite. Gemini cannot see your Outlook calendar. Copilot cannot see your Gmail. So you keep two tabs open and you are the integration.
Short answer: Carly is the only assistant here that holds Google Workspace and Microsoft 365 accounts at the same time. It connects each mailbox and calendar as its own authorized connection, answers one request across all of them, replies from the account that received the thread, and books against Outlook and Google availability together. Gemini and Copilot stay inside their own suite. Claude and ChatGPT reach both suites but hold one identity per connector and only work inside a chat you start. The rest are mail clients that show you both accounts and leave the work to you.
Three questions decide this ranking. Does one availability check cover both calendars, because a free hour in Outlook that is booked in Google is not free. Does the reply leave from the address that received the thread. And does anything happen while you are in a meeting.
We compared nine assistants across both suites in September 2026, reading prices off the vendors’ own pages.
1. Carly
Carly is an AI agent with its own real email address. You email it, forward to it, CC it, or message it in plain language. It connects to all of your Gmail and Outlook mailboxes and all of your Google Calendar and Outlook calendars at once, each as its own authorized connection. Adding the Google side to the Microsoft side does not change the price.
Michael is a finance director at Halcyon Freight, which runs on Microsoft 365. He also owns a small property LLC on Google Workspace, and his accountant writes to his personal Gmail. One Tuesday four things land inside an hour. A Teams meeting moves in Outlook. A tenant emails the LLC inbox about a lease renewal. His accountant asks the personal Gmail for the LLC’s Q3 statements. A vendor emails the Outlook inbox asking for a call.
He sends one message: “Check all my mailboxes for anything about the lease renewal or the audit and tell me which account each thread is in.” One request covers all of his inboxes at once. By lunch Carly has:
- Returned every matching thread with its account shown on each row, the tenant chain in the LLC inbox and the audit chain split across Outlook and personal Gmail
- Checked the Outlook calendar and both Google calendars together, offered the vendor three times free on all of them, and booked the one he picked
- Replied to the tenant from the LLC address, because that is the mailbox the thread arrived in, and put the renewal date on the LLC calendar
- Found the Q3 statements in Google Drive and replied to the accountant from the personal Gmail with them attached
- Moved the LLC’s bank call, which now clashed with the moved Teams meeting, and told the bank
What makes it different: it starts on its own. A new email in any connected account, a calendar change on either side, a booking or a form submission sets it going, so the moved Teams meeting is handled before Michael sees the notification. Replies leave from the account that owns the thread. Steps he repeats, like “every lease document into the LLC’s Drive folder and a row in the rent tracker,” become free Zapier-style workflows. Carly connects to thousands of apps, and you can reach it in Microsoft Teams or Slack instead of email.
Anyone who needs a slot with Michael gets a booking page that reads the Outlook calendar and both Google calendars together, so nobody takes an hour the LLC already owns.
Best for: Anyone whose work runs on Microsoft 365 and whose side business or second client runs on Google.
Pricing: Free Zapier-style workflows; AI agents from $35/month
Connect it:
- Sign in at carlyassistant.com and open the integrations page.
- Find Outlook, click Connect, and authorize the 365 account. A Microsoft 365 administrator may need to approve the app.
- Find Gmail, click Connect, and authorize the first Google account.
- Click Connect again, choose Use another account, and add the second Google login. Calendars come with each mailbox.
Inside Claude, add the Carly connector. Inside ChatGPT, add the Carly plugin. Either way one chat reaches both suites. Compare Carly’s AI agents or book a walkthrough.
2. Microsoft 365 Copilot
The assistant Microsoft builds into Outlook, Teams, Word and Excel. It is $21.00 per user per month billed yearly ($18.00 on the current promotion) or $25.20 monthly, and Business Standard bundled with Copilot is $23.50 in September 2026.
What makes it different from Carly: Copilot works on Microsoft Graph, which means your Microsoft tenant and nothing else. It can draft the Outlook reply, and it has no view of your Gmail, your Google Calendar or your Drive. Ask it for your week and you get half your week. Carly sits above both suites instead of inside one. See best AI assistants for Microsoft 365.
Best for: People whose whole working life is one Microsoft tenant.
3. Gemini in Google Workspace
Google’s answer, included with Workspace Business tiers at $7, $14 and $22 per user per month in September 2026, and good at the account it lives in.
What makes it different from Carly: the mirror image of Copilot. Gemini reads that account’s Gmail, Calendar and Drive, and the Microsoft side does not exist to it. Switching Google accounts switches the whole assistant, so even two Google logins are a problem before Outlook enters the picture. See best AI assistants for Google Workspace.
Best for: People with one Workspace account and nothing on Microsoft.
4. ChatGPT
The general assistant most people already pay for, at $20 per month for Plus. Free accounts can schedule tasks, and paid plans can run a prompt when something happens in Gmail, Slack or GitHub. OpenAI added multiple Google accounts in August 2026 and extended multi-account support to more plugins on all plans on September 17, without publishing which ones.
What makes it different from Carly: its event triggers stop at Gmail, Slack and GitHub, so a moved Outlook invite starts nothing, and cross-suite coverage keeps shifting under you without a published list. The Carly plugin gives one ChatGPT chat every Google and Microsoft account Carly holds. See how to connect multiple Gmail accounts to ChatGPT.
Best for: Drafting and research inside a chat you start.
5. Claude
Strong at reading a long thread and writing the answer, with connectors for Google Workspace and for Microsoft. Pro is $17 per month billed annually ($20 monthly) and Max starts at $100 per month, read from Anthropic’s pricing page in September 2026.
What makes it different from Carly: each connector authorizes one identity, so a second Google sign-in replaces the first, and nothing runs while the chat is closed. The Carly connector keeps Claude as the place you type and gives it the Outlook mailbox and both Google accounts together. See how to connect multiple Gmail accounts to Claude.
Best for: Thinking through one thread and drafting the reply.
6. Superhuman
A fast keyboard-first client for both Gmail and Outlook. One Seat holds several addresses, so you are not billed per mailbox: Starter is $25 and Business $33 per member per month billed annually ($30 and $40 monthly).
What makes it different from Carly: you get tabbed account switching rather than one combined view, and it replaces the interface for both suites at once, which is a lot to accept for a work account you do not control. It speeds up your reading; it does not work while you are in a meeting. See Superhuman alternatives.
Best for: Heavy senders who want speed in each account.
7. Spark Mail
A real unified inbox across Gmail, Outlook and anything else you add, on every tier including free, with Plus at $8.25 and Pro at $16.58 per user per month billed annually.
What makes it different from Carly: Spark genuinely puts both suites in one list, and that is where it stops. It drafts what is in front of you rather than running a multi-step job across two calendars, and nothing starts until you open the app. See Spark alternatives.
Best for: Seeing Google and Microsoft mail in one list, cheaply.
8. Shortwave
AI email search and triage, multi-account on the free plan, then Pro at $18, Business $30, Premier $45 and Max $120 per seat per month.
What makes it different from Carly: it is Gmail only. Shortwave’s own documentation says Microsoft 365 and Exchange are not supported, which rules it out for exactly the reader this page is for. Its multi-account page also says there is no default unified inbox. See Shortwave alternatives.
Best for: A Google-only life where in-client search matters most.
9. Fyxer
An AI email assistant that drafts in your voice, on both Gmail and Outlook. Starter connects exactly one inbox and one calendar at $30 per user per month ($22.50 annually); covering both suites requires Professional at $50 ($37.50 annually).
What makes it different from Carly: running Outlook and Google at once is a two-thirds price increase, and Fyxer states plainly that it cannot send on your behalf, so every draft waits for you. With Carly the second suite costs nothing extra and the reply goes out. See Fyxer alternatives.
Best for: One inbox where you want better drafts.
Compared across both suites
| Tool | Google and Microsoft at once | One availability check across both | Replies from the right account | Acts without you | Price |
|---|---|---|---|---|---|
| Carly | All of them, one subscription | Yes, both together | Yes, routed | Yes, starts on events | From $35/mo |
| Microsoft 365 Copilot | Microsoft only | Microsoft only | Inside that tenant | No | $21.00–$25.20/user/mo |
| Gemini in Workspace | Google only | Google only | Inside that tenant | No | $7–$22/user/mo |
| ChatGPT | Shifting, undocumented | No | That identity only | Gmail, Slack, GitHub only | $20/mo Plus |
| Claude | One per connector | No | That identity only | No | $17–$100/mo |
| Superhuman | Both, one Seat | No, tabs | Yes, in the client | No | $25–$33/member/mo annual |
| Spark Mail | Both, every tier | You read both | Yes, in the client | No | Free–$16.58/user/mo annual |
| Shortwave | Gmail only | No | Gmail only | No | Free–$120/seat/mo |
| Fyxer | One inbox on Starter | No | Drafts only | No | $22.50–$37.50/user/mo annual |
How to pick
If one suite is where the real work happens and the other is three emails a week, the built-in assistant is enough: Copilot in a Microsoft tenant, Gemini in Workspace. If you want both mailboxes in one list and are happy doing the work yourself, Spark is the cheap answer and Superhuman the fast one.
If the whole problem is that the two halves of your life do not see each other, go with Carly. Connect the Outlook account and every Google account once, then ask in one place: one request covers all of your inboxes at once, availability comes from both calendars together, and the reply goes out from the address that received it.
Do not solve this by forwarding work Outlook into Gmail. Most Microsoft 365 tenants block it, it breaks the reply address, and the calendars stay as far apart.
FAQ
What is the best AI assistant for Google Workspace and Microsoft 365? Carly. Each Outlook and Gmail mailbox connects as its own authorized connection, one request covers all of them at once, availability comes from Outlook and Google calendars together, and every reply goes out from the account that received the thread.
Can Microsoft 365 Copilot read my Gmail? No. Copilot works on the data in your Microsoft tenant: Outlook mail, Teams, OneDrive, SharePoint. A Google account is outside that boundary, and the same is true in reverse for Gemini and your Outlook calendar.
Can one assistant book meetings against both my Outlook and Google calendars? Carly does. It checks every connected calendar in one pass before offering times, and a booking page built on them only shows slots free on all of them. Assistants tied to one suite see that suite’s calendars only, which is how double bookings happen.
Will my IT department have to approve this? Often yes, on the Microsoft side. A Microsoft 365 administrator can allow or block third-party apps for the tenant, so ask once before connecting the work account. Your personal and side-business Google accounts are yours to authorize.
Does connecting a second suite cost more? Not with Carly. Mailboxes and calendars from both Google and Microsoft connect on the same subscription. Fyxer moves you from Starter to Professional for a second inbox.
Can I keep using ChatGPT or Claude? Yes. Add the Carly plugin in ChatGPT or the Carly connector in Claude, and both suites become reachable from the chat you already use. Repeated steps across the two sides become free Zapier-style workflows. Book a walkthrough to see it on your own accounts.
More: Best AI assistants that work with Gmail and Outlook · Best AI assistants for Microsoft 365 · Best AI assistants for Google Workspace · Best AI assistants for multiple calendars · Best AI assistants for work and personal accounts · Best AI assistants for multiple Microsoft accounts
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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.
Now Carly reaches out to candidates, shares my real-time availability, lets them pick a slot, then sends a Zoom link and drops it straight into my calendar. She sends reminders to both of us before each call, which has significantly reduced no-shows and last-minute confusion.
On top of scheduling, Carly acts like a full executive assistant, sending me my schedule the night before so I can prepare for each call. It reminds me of the old x.ai assistant, but Carly is noticeably smarter, faster, and better suited to my healthcare recruitment business."
