SMTP Issues with Office 365

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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. 

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?

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?

• smtp

Share Improve this question edited Jul 4, 2019 at 16:06 molecoder 11366 bronze badges asked Jan 6, 2017 at 16:50 bhoodbhood 25722 gold badges33 silver badges99 bronze badges 3

• Office365 also supports SSL on port 465, have you tried that? I've found PHPMailer to be notoriously buggy with TLS. – TheGentleman Commented Jan 6, 2017 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 Commented Jan 6, 2017 at 18:44
• 2 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 Commented Jan 6, 2017 at 19:14

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1 Answer 1

Sorted by: Reset to default 1

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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