Send & Receive Issues

How to Fix MacBook Pro Cannot Send Hotmail Emails

Khadija Khan Oct 10, 2026 868 views

Question details

The user is unable to send emails from their Hotmail account using a MacBook Pro, although the account continues to receive emails and functions perfectly on their iPhone and iPad.

Fix MacBook Pro Cannot Send Hotmail Emails

Product: Mac Mail
Device & OS: macOS
Scenario: Attempting to send outbound Hotmail messages via the macOS Mail app after recently adding an Exchange account to the device.
Observed behavior: Outgoing messages remain stuck or fail to send completely, even without attachments, due to a suspected conflict with the newly added Exchange configuration.

Before you start

Ensure your MacBook Pro is connected to a stable Wi-Fi network and verify that you know your current Hotmail password before making changes to your Internet Accounts settings.

Solution 1Recommended

Remove Conflicting Exchange Account and Re-authenticate Hotmail

Since the sending failure began after adding an Exchange account, removing the conflicting setup and re-authenticating your primary Hotmail account usually resolves the outgoing server conflict.

macOS Mail can sometimes confuse SMTP (outgoing server) authentication tokens when multiple Microsoft-based accounts (like Exchange and Hotmail/Outlook) are added simultaneously. Clearing the configuration forces the system to request fresh, correct credentials.

Open Internet Accounts

Click the Apple menu () in the top-left corner of your screen, select 'System Settings' (or 'System Preferences'), and click on 'Internet Accounts'.

Delete the Conflicting Account

Select the recently added Exchange account from the list. Click the 'Delete Account' button (or the minus '-' icon) at the bottom to remove it from your Mac.

Re-authenticate Hotmail

Select your existing Hotmail account in the same list. If prompted, click 'Details' or enter your password to refresh the connection.

Test Outgoing Mail

Open the Mac Mail app, compose a new email using your Hotmail address, and send a test message to yourself to verify the fix.

Remove Conflicting Exchange Account and Re-authenticate Hotmail

Safe Account Removal: Removing an Exchange or IMAP email account from your Mac does not delete your emails from the server. They will resync securely if you decide to add the account back later.

Solution 2

Manually Verify and Update Hotmail SMTP Settings

If re-authenticating doesn't work, manually checking your Outgoing Mail Server (SMTP) settings ensures Mac Mail is routing your Hotmail messages through the correct Microsoft servers.

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Frequently Asked Questions

Why can I receive Hotmail emails on my Mac but not send them?

Receiving and sending emails rely on two different servers (IMAP for incoming and SMTP for outgoing). If your incoming settings are correct but your outgoing settings lack proper authentication or are pointing to an incorrect port, you will receive emails without being able to reply or send new ones.

Does adding an Exchange account interfere with Hotmail on macOS?

It can. Since Exchange and Hotmail both utilize Microsoft’s backend infrastructure, macOS Mail sometimes merges outgoing server profiles or misallocates authentication tokens, causing one of the accounts to lose sending capabilities.

What are the correct SMTP server settings for Hotmail on a Mac?

The standard outgoing (SMTP) server for Hotmail is smtp-mail.outlook.com (or smtp.office365.com). It requires Port 587, STARTTLS/SSL encryption enabled, and a standard password authentication using your complete Hotmail email address.

Why does Hotmail work perfectly on my iPhone but fail on my MacBook Pro?

iPhones and iPads handle email account provisioning slightly differently through iOS Profiles, which often auto-configure and isolate Microsoft servers more cleanly than the desktop macOS Mail application. Syncing issues on the Mac do not affect your iOS devices.

Outlook & Email Problems