SMTP Not working

[MSzczeblewski]

Not sure if you still keep up or are still interested. Pushbullet has been timing out sending notifications, only about half go through. I am sure it is on their end.
Tried to get SMTP working with my gmail account. Tried ports 587 and 465. 587 just sends back some kind of authentication error and the other port just doesnt work.

[Kapps]

I suspect that you need to enable sending email through SMTP. I think Gmail started disabling that by default.
https://www.lifewire.com/what-are-the-gmail-smtp-settings-1170854 - in particular, the stuff about less secure apps.

[MSzczeblewski]

I enabled the less secure setting on gmail.
Also tried generating a custom password for the client. That did not work either.

When trying to send a test message I get:
<Failed to send SMTP notification: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required. Learn more at>