I spent quite a bit of time trying to nail down the specific settings for sending programmatic emails through Gmail (using swaks to verify).
I figured I would document it here in case it helps anyone else.
Following this link (and enabling 2FA/two-factor-authentication), then create an app password to use for signing into the mail server.
Docker route (not required, other swaks Docker images exist, but this was the most useful)...
swaks.Dockerfile
```
FROM ubuntu:20.04
RUN apt update && echo y | apt install swaks vim
```
Build...
`docker build -t swaks $PWD\swaks.Dockerfile`
Run...
`docker run -it --rm swaks sh`
Finally, try test email...
swaks -4 --server smtp.gmail.com -tlsc --tls-protocol TLSv1_2 \
--from [your full gmail account email that app password was setup for] --to user1@example.com,user2@example.com \
--auth LOGIN --auth-user [same as from] --auth-password [your generated app password] -apt \
--h-Subject 'Test email' --body 'Email system test.'
The -apt argument isn't required of course, it just helped with troubleshooting. Not using "smtp-relay..." for the server as what little Google documentation exists indicated, was necessary. Do not consider this a "secured" example, merely for testing purposes.
I'll try closing this "issue" if allowed so as to not create more work for admins.
I spent quite a bit of time trying to nail down the specific settings for sending programmatic emails through Gmail (using swaks to verify).
I figured I would document it here in case it helps anyone else.
Following this link (and enabling 2FA/two-factor-authentication), then create an app password to use for signing into the mail server.
Docker route (not required, other swaks Docker images exist, but this was the most useful)...
swaks.Dockerfile ``` FROM ubuntu:20.04 RUN apt update && echo y | apt install swaks vim ``` Build... `docker build -t swaks $PWD\swaks.Dockerfile` Run... `docker run -it --rm swaks sh`Finally, try test email...
The
-aptargument isn't required of course, it just helped with troubleshooting. Not using "smtp-relay..." for the server as what little Google documentation exists indicated, was necessary. Do not consider this a "secured" example, merely for testing purposes.I'll try closing this "issue" if allowed so as to not create more work for admins.