O365 and Gmail SMTP Not Working

Using Formidable as my contact form plugin, and trying to get WP Mail SMTP to work because our web hosting is a rat’s nest of complication and I barely have any idea what I’m doing in order to try to get php mail functionality to work. I don’t even know if MTA or postfix is installed. I don’t even really know what those even are.

I feel like just using a WordPress-specific host might alleviate this issue but I’m trying to see if I can get this to work before we take that route.

Anyway…

Our email addresses are all through Office 365

When trying to configure WP Mail SMTP, I’ve entered all the SMTP info for Office 365:

Office 365 SMTP Settings
Host: smtp.office365.com
Port: 587
Username: Your Office 365 account email
Password: Your Office 365 account password
Encryption: TLS

However, when I try to send a test email, I get this error:

There was a problem while sending a test email. Related debugging output is shown below:

Versions:
WordPress: 4.9.4
WordPress MS: No
PHP: 5.6.34
WP Mail SMTP: 1.2.5

Params:
Mailer: smtp
Constants: No
ErrorInfo: SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting
Host: smtp.office365.com
Port: 587
SMTPSecure: tls
SMTPAutoTLS: bool(true)
SMTPAuth: bool(true)

Server:
OpenSSL: Yes
SMTP Debug:

The same thing happens when trying to use Gmail SMTP:

Gmail's Default SMTP Settings
Gmail SMTP server address: smtp.gmail.com
Gmail SMTP username: Your Gmail address (e.g. [email protected])
Gmail SMTP password: Your Gmail password
Gmail SMTP port (TLS): 587
Gmail SMTP port (SSL): 465
Gmail SMTP TLS/SSL required: yes

There was a problem while sending a test email. Related debugging output is shown below:

Versions:
WordPress: 4.9.5
WordPress MS: No
PHP: 5.6.35
WP Mail SMTP: 1.2.5

Params:
Mailer: smtp
Constants: No
ErrorInfo: SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting
Host: smtp.gmail.com
Port: 587
SMTPSecure: tls
SMTPAutoTLS: bool(true)
SMTPAuth: bool(true)

Server:
OpenSSL: Yes
SMTP Debug:

Can someone point me in the right direction here?

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