Gmail 'send as' can't connect

This has been driving me crazy all day.

I’ve set up new servers, restored the backed up domains on them, updated the dns, and things all work… except for my users using Gmail send-as. Gmail is saying it can’t connect.

I tested the connection using SMTP Test Tool (same port and with TLS) and it connected fine and was able to send mail with no trouble.

That would suggest to me that the connection is viable. It’s available. This is something specific to Gmail (I think).

I’m using cloudflare. I have the mx record as mail.andrews.com and an A record from mail.andrews.com to 31.220.100.231 (these are not proxied).

I do not have mail.andrews.com set up as a virtual server in my virtualmin console. I’ve never been sure if I’m supposed to have that or not. I set one up and it did not make a difference. The gmass test works either way. Gmail doesn’t work either way (can’t connect).

mail.andrews.com is listed on my andrews.com letsencrypt cert as an additional domain.

Luckily I provide the email to these users as a volunteer, they are not paying customers, so they can’t get too upset, but I want to provide reliable email to them.

I’m stuck, any thoughts on what I might try?

Thanks,

Chris

Ubuntu Linux 22.04.2
Webmin 2.105
VM: 7.9.0

Virtualmin recommended settings are in edit users section, did you try them?

I had not seen that, but I tried the settings there and still got the same error from Gmail… thanks though,

Chris

Turned Fail2Ban off, no change.

use port 465/587 also make sure postfix has configured valid ssl certiifcate for the domain on which you’re trying to connect.

I FOUND IT!

Yea! I get to go to bed tonight instead of fighting with this all night long :rofl:

Ok, here’s what all that was about. IPv6. I had set up AAAA records for mail, used the IPs that my hosting company gave me… and didn’t think anything of it. I was focused on the IP4 more, thinking that was primarily used.

And with the testing I did, apparently that used IP4.

But Gmail defaults to using IP6, and after I deleted the AAAA records, Gmail rolled down to using the IP4 and that worked.

Apparently my hosting company gave me IP6 but it wasn’t actually connected? I don’t know, I’m going to ask them about that, but apparently it wasn’t.

Whew!

It’s always the information that the poster (me!) doesn’t include that ends up being the answer.

Thank you Stefan and Naresh for chipping in potential solutions!

Chris

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