LAN SMTP relay configuration issue

installation
1

Hello,

I have installed the latest release on the latest release of Ubuntu (18.04)

As with many other people I have a problem configuring SMTP.
We have a SMTP relay that runs in our network and Office 365 account that can be used, but I spent the last few days trying with no luck.

It appears that O365 does not support an authentication method supplied in Discourse, so I gave up on that.

When trying to configure the LAN relay, I found that the container (or perhaps the docker in general) does not inherit the host DNS. I was getting errors that my local SMTP server was not found

tcpdump -i docker0 -n port 53

does show that 8.8.8.8 is being used, and all LAN addresses are invisible.

further efforts led me to create a /etc/docker/daemon.json with the following
{ "dns": ["192.168.1.33", "8.8.8.8"], }

but once that file is created, the docker service does not start

I get exactly what is described in this topic - debian - docker service does not start after creating daemon.json - Stack Overflow

If anyone could assist me in resolving this issue, it would be much appreciated. We’d really like to use Discourse, but without SMTP, it’s pretty useless to us.

2

so far, we’ve given up and reconfigured to O365 and it suddenly worked… we’re at the point of making a few tweaks and not being sure what made it work… nevertheless - Office 365 config works with the following:

DISCOURSE_SMTP_ADDRESS: 'smtp.office365.com'
DISCOURSE_SMTP_PORT: 587
DISCOURSE_SMTP_USER_NAME: 'your.email@domain.com'
DISCOURSE_SMTP_PASSWORD: 'password'
DISCOURSE_SMTP_AUTHENTICATION: login
DISCOURSE_SMTP_ENABLE_START_TLS: true
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