kboutelle

Thank you very much for the verification and extra info.

It's poor form to reply to your own post, but I fixed this and thought I'd report back to let folks know what I did. I'm using the RA virtual appliance, so I enabled Webmin and took a look at what needed to be updated on the server. I ran the updates that were available, fixed the subsequent MySQL connectivity issues that resulted from the updates, and tried again. Lo and behold, everything worked. With a few changes... Password - re-entered the same password as above (copy & paste) Port - 465 That's it. I thought it might be the Linux Firewall but no. All outbound was allowed by default. So there must have been an update that was needed or when I thought I checked port 465 yesterday, I just needed to re-enter the password. I'm sorry I can't pinpoint the exact thing that fixed this, but the reality is that there shouldn't have been an issue to begin with.

I'm setting up the SMTP Server settings in eSet Remote Administrator v6.5.417.0 and I'm using the following settings and I cannot get eSet RA to send email. The Send test email function fails with the timeout (Test email has not been successfully sent. Request timeout 90000ms exceeded.) Should this service work with Gmail at all? Is there something that I'm missing? (all settings are identical to other services that I have that are working to send email reports regularly) Host - smtp.gmail.com Port - 587 Username - verified user in G Suite Password - verified app password for user above Connection security type - TLS Authentication type - Automatic (I've tried External, Plain, Login and Automatic)