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I'm having issues setting up SMTP for Office 365 using the Easy WP SMTP plugin. I keep getting the following vague error message.

SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting

I've looked through most of the Troubleshooting documentation and have had no luck. Please see the image below for the settings I'm using. It seems like other people have experienced the same issue with Office 365. Any ideas?

enter image description here

  • Office365 also supports SSL on port 465, have you tried that? I've found PHPMailer to be notoriously buggy with TLS. – TheGentleman Jan 6 '17 at 17:19
  • @GentlemanMax yeah, unfortunately no luck using SSL on port 465...are there security settings within Outlook 365 you think I should change? – bhood Jan 6 '17 at 18:44
  • Probably not but it couldn't hurt to check. Have you tried setting up the account in outlook/thunderbird/etc to see if it works there? – TheGentleman Jan 6 '17 at 19:14
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Your goal is to send emails, using that specific plugin isn't a requirement.

Therefore, I suggest you install and activate instead the WP Mail SMTP plugin.

Once it's active, go to Settings > WP Mail SMTP to configure the plugin settings.

This will ask you to enter the email address and a from name (similar to the picture you shared).

What comes next can be tricky.

First, choose the mailer. For your case, select Other SMTP.

After that, check the box Return Path.

Next, you need to set up SMTP options (SMTP host and port, encryption, select authentication toggle and provide your SMTP username and password), just like you did in your image.

Then there's a testing tab which you can use to test if everything works fine. It's very straightforward.

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