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Send As Outlook or Hotmail From Gmail in 2027: Options

Updated 2026-10-03 · by Adam Hale

After January 2027 you can't send as an Outlook or Hotmail address from Gmail on the web, and SendAs Relay doesn't support Outlook.com, Hotmail or Live addresses yet either. Microsoft has required modern sign-in (OAuth) for these mailboxes since September 16, 2024, so any tool that takes a password or app password can't send for them. What works today: Microsoft's Outlook apps, the Gmail mobile app with the account added separately, Thunderbird with OAuth2, and outlook.com itself.

Why Outlook.com and Hotmail are different

Most providers (Yahoo, AOL, iCloud, GMX) still let other apps send with an app password. Microsoft does not:

Send as Outlook or Hotmail from Gmail: what still works

Option Where Cost Notes
Outlook mobile or new Outlook for Windows Phone or PC Free Uses Microsoft's own sync, not SMTP. Can also add your Gmail account, so both live in one app
Gmail mobile app, Outlook added separately Phone Free Google says this "will not change". We haven't confirmed whether sending works for newly created mailboxes with SMTP disabled (not yet confirmed)
Thunderbird with OAuth2 Desktop Free Microsoft documents the OAuth2 setting for Thunderbird. Sending uses SMTP, so the new-mailbox problem above may apply
Apple Mail, added as "Outlook.com" Mac, iPhone Free Microsoft says Apple Mail uses modern authentication when set up this way
outlook.com in a browser tab Anywhere Free The simplest fallback

Microsoft's own advice for apps that don't support modern authentication is to use Outlook, which is free on Windows, Mac, iOS and Android (Microsoft support).

Keep reading Outlook mail in Gmail

Incoming mail is the easy half. Outlook.com supports automatic forwarding: Settings, then Mail, then Forwarding. Microsoft may ask you to turn on two-step verification first (Microsoft support). Forwarded mail then gets Gmail's spam filter and search. Replies are where you need one of the options above.

Options that look like fixes but aren't

If you're ready to retire the Hotmail address

Many people keep an old Hotmail address only for legacy contacts and accounts. A low-effort path:

  1. Turn on forwarding from Outlook.com to Gmail so nothing is missed.
  2. Reply from your Gmail address, or from a custom domain, and tell contacts to update their address book.
  3. Update logins at banks, stores and services over a few months.
  4. Keep signing in to Outlook.com now and then, since Microsoft can close inactive accounts (unverified: we didn't re-check Microsoft's current inactivity rules for this guide).

Google's warning, applied to Outlook

Google cautions against third-party "Send as" tools because they "often require access to your email credentials or OAuth tokens". For Outlook.com, any third-party sender would need an OAuth token from Microsoft. That is better than a password, because it is scoped and revocable in your Microsoft account. It is still a key to your mailbox, so treat it as one.

How SendAs Relay fits

Honestly: not for Outlook.com, Hotmail or Live addresses today. SendAs Relay sends through SMTP with a password or app password, which Microsoft doesn't allow for these mailboxes. Microsoft sign-in support is planned but not built, and we won't promise a date.

If you also have a Yahoo, AOL, iCloud, GMX or custom-domain address, SendAs Relay can handle those. It's a Firefox (140+) and Edge (137+) extension that adds a From picker to Gmail on the web. Mail goes out through each address's own SMTP server via a stateless, open-source relay that you can host yourself, and credentials stay in your browser. See how it works and the FAQ.

For Outlook.com today, use the Outlook app, the Gmail app or outlook.com.

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