Cannot send message using SMTP server

I configured my iCloud account with OS Sierra 10.13.6. When I go to Mail I can receive emails without any issues but I cannot send.

I have researched around the web and these are the steps I have tried:

Under Mail - Preferences - Accounts, I selected my iCloud account (which shows IMAP). Under the Server Settings tab - Outgoing Mail Account I added SMTP.mail.me.com.

I added my iCloud email under User Name. Entered my password. Under host name I entered smtp.mail.me.com. I checked the option for automatically manage my connection settings.

Still the SMTP account shows offline. This is the error I get:

Cannot send message using the server SMTP

Connections to the server “smtp.mail.me.com” on the default ports timed out.

Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent.


Please help!

MacBook Pro TouchBar and Touch ID, macOS Sierra (10.12.6)

Posted on Sep 2, 2018 6:50 PM

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Sep 3, 2018 7:32 PM in response to OzzieInTX

Try the Safe Mode.


Safe Mode - About


Safe Mode Startup – El Capitan. also Sierra


If it works in the Safe Mode, try running this program when booted normally and then copy and paste the output in a reply. The program was created by Etresoft, a frequent contributor. Please use copy and paste as screen shots can be hard to read. Click “Share Report” button in the toolbar, select “Copy to Clipboard” and then paste into a reply. This will show what is running on your computer. No personal information is shown. You can run the report for free at least once, but if you run it several times, at some point it will ask you to pay a license fee.

Etrecheck – System Information


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Cannot send message using SMTP server

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