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Outlook Setup and Troubleshooting

Add email accounts, set up signatures, sync calendars, and fix common send/receive issues in the new Outlook

The "new Outlook" is now the default email client on both Mac and Windows. It's a cleaner, web-based design that replaces the classic Outlook most people are used to. This guide covers the essentials: adding accounts, creating signatures, syncing calendars, and fixing the most common problems.

Classic Outlook is being phased out. On Windows, the new Outlook is now the default for new Microsoft 365 installations, though you can still switch back to classic temporarily using the toggle. On Mac, the legacy Outlook app is scheduled to lose support for new Exchange Online connections. If you're still on classic, now is a good time to switch.

Add an email account:

  1. Open Outlook and go to Outlook > Settings in the menu bar (or press Cmd + ,)
  2. Click Accounts
  3. Click Add Account
  4. Enter your email address and click Continue
  5. Follow the sign-in prompts for your provider (Microsoft 365, Google, iCloud, or IMAP)
  6. Once verified, your inbox, calendar, and contacts sync automatically

For work or school accounts using Microsoft 365, you may see an authentication prompt from your organization. Sign in with your work credentials and approve any multi-factor authentication requests.

Create a signature:

  1. Go to Outlook > Settings (or Cmd + ,)
  2. Click Signatures
  3. Click the + button to create a new signature
  4. Name it and type your signature in the editor
  5. Use the formatting toolbar to add links, images, or styled text
  6. Under Default signatures, choose which signature to use for new messages and replies
  7. Close the settings window to save

You can create multiple signatures and switch between them while composing. Click the three-dot menu in the compose toolbar and select Insert Signature.

Calendar sync:

Calendars sync automatically when you add an account. If a calendar isn't showing:

  1. Click the Calendar icon in the bottom-left of the Outlook window
  2. In the left sidebar, check that your account's calendars are toggled on
  3. If a shared calendar is missing, click Add calendar > Subscribe or ask the calendar owner to re-share it

Troubleshoot send and receive issues:

  1. Check your internet connection. Outlook shows a "Disconnected" or "Trying to connect" message in the top bar if it can't reach the server
  2. Quit Outlook completely (Cmd + Q) and reopen it
  3. Go to Outlook > Settings > Accounts, select the problem account, and click Remove, then add it again
  4. If Outlook keeps crashing or won't open, reset it: open Finder, press Shift + Cmd + G, go to ~/Library/Group Containers/UBF8T346G9.Office/Outlook, and rename or delete the Outlook Profile folder, then reopen Outlook

For persistent issues, try repairing Office: open any Office app, go to Help > Check for Updates, install any available updates, and restart.

Frequently Asked Questions

What happened to classic Outlook?▾

Microsoft is phasing out classic Outlook in favor of the new Outlook, which is built on the same engine as Outlook on the web. On Windows, the new version is now the default for new Microsoft 365 installations, but you can still switch back to classic temporarily. On Mac, legacy Outlook is scheduled to lose support for new Exchange Online connections. Classic Outlook will continue receiving security updates for a transition period, but new features are only being added to the new version.

Can I use Outlook with a Gmail account?▾

Yes. The new Outlook supports Google accounts natively. When adding an account, enter your Gmail address and sign in through Google's authentication flow. Your Gmail inbox, contacts, and Google Calendar will sync into Outlook. Some Gmail-specific features like labels don't translate perfectly (they show as folders), but mail, calendar, and contacts work well.

Why are my emails stuck in the outbox?▾

This usually means Outlook can't connect to the mail server. Check your internet connection first. Then try closing and reopening Outlook. If the email is still stuck, open the outbox, double-click the stuck message, and try sending it again. Large attachments (over 20 MB for most providers) are a common cause. Compress the file or share it via OneDrive instead. If nothing works, remove your account from Settings > Accounts and add it back.

Can I still use classic Outlook if I prefer it?▾

For now, yes. On Windows, you can toggle back by clicking the switch labeled "New Outlook" in the top-right corner of the new Outlook window. On Mac, if you have the legacy version installed, you can still open it. However, Microsoft is gradually removing the toggle and pushing everyone to the new version, so it's worth getting comfortable with it now.

Why is my calendar not syncing?▾

First, make sure the calendar is toggled on in the sidebar. If it's a shared calendar, the owner may need to re-share it with your account. For Google Calendar in Outlook, sync can take a few minutes after initial setup. If nothing shows up after 10 minutes, remove and re-add the account. For Exchange or Microsoft 365 calendars, check with your IT admin to make sure calendar sync is enabled for your account.