If your Mac is connected to the Internet but suddenly stops sending email, you should generally try again later, and if necessary work with your email provider to resolve. If you're using Apple's iCloud Mail, learn how to resolve issues with iCloud Mail.
Jun 04, 2019 Describes how to enable logging in Microsoft Outlook for Mac and how to collect logs, log file locations, and other important information about logging in Outlook for Mac. How to enable logging in Outlook for Mac. Content provided by Microsoft. Sender and receiver’s email addresses, and the contents of the user’s email. This feature is only available in Outlook 2016 for Mac 15.36.1 (170721) and later with an Office 365 subscription and Outlook 2019 for Mac (select Outlook About Outlook to check your version).
Check for status messages
You might see a status icon such as a lightning bolt or warning symbol next to your account's inbox in the Mail sidebar, or in the upper-right corner of the Mail window. Click it to learn more.
Test using webmail
Many email providers offer webmail, which is a way to use email with a web browser such as Safari, instead of with an email app such as Mail. For example, if you're using an iCloud Mail account, you can use iCloud.com to send and receive email.
Webmail is a good way to verify that your account is valid and you can sign in to it from the web, but it doesn't mean that your account is set up correctly in Mail. Your email provider can help you verify your email settings and check for other issues that affect sending or receiving email.
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Mail User Guide
An email alias is like a nickname and helps to keep your actual email address private. When you send emails using an alias, your recipients never see your actual email address.
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