Email not sending attachment

An error occurred while attempting to establish an SSL or TLS connection. The server’s SSL certificate could not be validated for the following reasons: • The server certificate has the following errors: • The revocation function was unable to check revocation for the certificate

As per troubleshooting section under your SMTP Server screen, there is a checkbox Do not verify TLS certificate so try checking that.

See: https://www.manager.io/guides?email-settings-form

Test email works but when go to send it says

An error occurred while attempting to establish an SSL or TLS connection. The server’s SSL certificate could not be validated for the following reasons: • The server certificate has the following errors: • The revocation function was unable to check revocation for the certificate.

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Lubos

I have tried 3 different email accounts for SMTP

It sends an email correctly but when I go to send invoice or something else it does not work

What am I doing wrong?

If test email settings are ok,
What if you send an email without attachments? does this work?

So far email is working fine in Manager.
Maybe you need to try another email provider such as Gmail or Yahoo.

As far as I am aware the SMTP server for outlook 365 is:
smtp-mail.outlook.com

You wrongly use the IMAP (incoming) outlook.office365.com in your screenshot.

@Mabaega uses the correct SMTP server: smtp-mail.outlook.com and therefore has no issues.

It was the avg anti virus

When disabled worked fine

Thank you