Connect Gmail or Outlook

Connecting takes a moment. You sign in through Google or Microsoft, review what Chiefy is asking for, and approve it. From then on, Chiefy can read your inbox and prepare drafts for you — all through your provider’s secure sign-in, so you never share your password with us. In Gmail, you work with Chiefy right in the side panel; Outlook inboxes are connected and worked on in the background, since the in-mail side panel is Gmail-only today.

Before you start

You’ll need the Chiefy extension installed. New to Chiefy? Start with Install the Chiefy extension first, then come back here.

Start sign-in

There are two ways to begin, and both lead to the same secure sign-in screen.

1. Open sign-in from Gmail or the web

   Click the Chiefy icon in Gmail to open the side panel, or go to app.chiefy.com directly. Either one starts the sign-in flow.

   Chiefy · Sign in

   Chiefy

   Your AI chief of staff for Gmail and Outlook — drafts replies in your voice, organizes your inbox, and keeps your day on track.

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   Connect the inbox you want to use with Chiefy

   Continue with Google Continue with Microsoft

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2. Choose your provider

   Pick Continue with Google to connect Gmail, or Continue with Microsoft to connect Outlook. Chiefy hands you off to that provider’s own sign-in page to finish authenticating.

3. Review and approve access

   On your provider’s screen, sign in to the account you want to use and review the access Chiefy is requesting. Gmail asks you to allow Chiefy to read, compose, send, and manage your email; Outlook asks for the equivalent. Approve it to continue.

Chiefy needs full mailbox access to do its job — reading threads to summarize them, and creating drafts in your voice. It only ever prepares drafts; nothing is sent without you.

What access Chiefy asks for

Sign-in uses OAuth, the standard way to grant an app access without sharing your password. You authorize Chiefy on Google’s or Microsoft’s own screen, and you can revoke that access from your provider’s account settings at any time.

• Gmail uses Google OAuth. Chiefy requests permission to read, compose, send, and manage your Gmail, plus your basic profile and email address to identify your account.
• Outlook uses Microsoft OAuth, which grants the equivalent access to your Outlook mailbox.

What happens after you approve

Once you approve, Chiefy completes sign-in and your inbox is connected.

• You’re taken into a short setup flow — a pricing step, then a confirmation — so Chiefy is ready in your inbox.
• At the pricing step, first-time users start a 14-day free trial with no charge until it ends. If you’ve used a trial before, you’ll go straight to choosing a plan.
• The extension notices you’re signed in automatically. It watches a small sign-in marker that the connection sets, so it picks up sign-in, sign-out, and routine session refreshes without you doing anything.

After that, if you connected Gmail, reload it when it’s open and the Chiefy side panel is ready to use. If you connected Outlook, there’s nothing to reload — Chiefy starts working on your inbox in the background.

If sign-in doesn’t work

If something goes wrong, Chiefy shows a message tailored to your provider — Google or Microsoft — with guidance on what to try next. The most common cases:

• Wrong account. You signed in with a different account than the one you meant to connect. Sign out of that account with your provider, or start sign-in again and pick the right one.
• Access not granted. You closed the provider’s screen or declined a permission Chiefy needs. Start sign-in again and approve the requested access — Chiefy can’t read your inbox or prepare drafts without it.

If you approve everything and still can’t connect, try signing in from app.chiefy.com in a fresh tab. If you connected Gmail, reload it afterward so the side panel picks up your session.

Next steps

You’re connected. Next, see Your first five minutes with Chiefy to get oriented and see what Chiefy does with your inbox.