Dear chris,

            please mention your connection detailes for more info. And try to paste the error here or upload a screenshot.

            if you are using smtp server with gmail,

            the below detailes can be of help

            port:465

            smtp server : smtp.gmail.com

            connection security: SSL/TLS

               and make sure you have entered the correct login and password.

              Also try setting up the mail after loging in to the browser.

               and for gmail , you have to enable less secure apps in order to use odoo.

            To enable less secure apps

                    you can use this link:

                        https://myaccount.google.com/lesssecureapps?pli=1

I am having a similar problem with odoo version 12. It tells me connection lost anytime I try to send a quotation.

My smtp server is setup. It tells me everything is successful but still not sending emails.

DigitalOcean is known to block email ports such as 25, 587, 465 etc by default on most droplets. Please first make sure that you can connect to your SMTP service by doing:

telnet smtp.gmail.com 25

What do you get in response?

Further, I would recommend you use a transactional SMTP / Mail service to send emails out from Odoo, instead of gmail. Mandrill has a free plan that you can use.

Obviously you are not able to setup your SMTP account properly. However, you should not use the Gmail default SMTP server anyway, but the G-Suite relay SMTP server instead for obvious reasons. Please read Odony's answer here:

https://github.com/odoo/odoo/issues/21119

and Google's instructions here:

https://support.google.com/a/answer/2956491?hl=en

and follow the deployment instructions of Odoo here:

https://www.odoo.com/documentation/user/11.0/discuss/email_servers.html

@rishan I tried already. Didn't work better.

5.7.14 https://support.google.com/mail/answer/78754 q8-v6sm3808909wmb.3 - gsmtphen I try to connect with the Test connect with Gmail here is what I get: .

Here is current configuration I have on odoo 

Sign into google.

Goto google apps. (top right)

Select Account.

sign in and security->apps with account access.

Scroll down and turn on

Allow less secure apps...

That should do the thing......

first try with the gmail account using google smtp configuration.