Gmail is using our notification email address, not the reply-to email

AI-generated summary

nathank reports that Gmail and Outlook are not using the Reply-to address for email replies from their Discourse site, instead using the From address. They share their SMTP configuration using Mailgun and ask if they’re doing something wrong. pfaffman confirms that this behavior is unusual, as the Reply-to address should be used. Ethsim2 suggests matching the SMTP user domain with the notification and reply-to email addresses and changing the SMTP port from 2525 to 587.

When testing something else, I’ve noticed that Gmail isn’t playing nicely with reply by email from our Discourse site. The sent email seems fine:

However, the Gmail web interface, when I click ‘Reply’, I get the From address, not the Reply-to address:

This has also caught out a few of our users, who seem to be using Outlook.

This is my config (using Mailgun / mail-receiver)

DISCOURSE_SMTP_ADDRESS: smtp.mailgun.org
DISCOURSE_SMTP_PORT: 2525
DISCOURSE_SMTP_USER_NAME: postmaster@mg.spokes.nz
#DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true)
DISCOURSE_SMTP_DOMAIN: mg.spokes.nz
DISCOURSE_NOTIFICATION_EMAIL: notifications@spokes.nz

Am I doing something dumb?

That doesn’t seem right. We see the reply-to.

That makes it more strange.

match your SMTP user domain with notification email and reply by address, should work?

i’d untick and re-tick the reply-by-email checkbox, but also change from port 2525 to port 587