Diving back to why email doesn't go out / arrive

[David Dyer-Bennet]

Finally getting back to chasing the email problem I talked about back in https://www.truenas.com/community/t...lure-to-send-email-notifications-leave.97703/

Got the TrueNAS software up to TrueNAS-13.0-U2. I have the root user email set to "dd-b@example.com" (okay, not example.com, my real email address).

Email is configured to use the SMTP method, using the same smtp server, username, and password that works in my Thunderbird setup.

When I click "SEND TEST EMAIL" on that page it says it succeeded, and the messages in /var/log/maillog look reasonable. Furthermore, if I change the SMTP server name to something invalid, when I run a test I get a popup saying the test failed. The lack of error popup when I have the right server name in there seems hopeful.

The smtp server configured is at dreamhost. I've got the right username (the full email address, not just the user part). If I change the user name to something wrong, I get errors again, which I don't when the username is right. So I think it actually is right.

So....except for the actual email content, this should look externally (to the Dreamhost smtp server) exactly like me sending email from my Windows or Linux desktops via Thunderbird (or my cell phone via K9 mail, for that matter, when I'm on my home WIFI). And those all worked, have for decades, but this does not.

[this paragraph edited] Ah, tcpdump is present by default, so I don't have to worry about adding software. So I'm now working on capturing the actual server interaction when the test message is sent, maybe I'll learn something interesting, eh?

I've seen several people say that email sending is generally flaky in TrueNAS. Is that still true?

And...are other people successfully sending email through specifically the smtp.dreamhost.com server?

Working up towards checking to see if anybody has already submitted a Jira ticket, and doing one myself, if I can get all the ducks in the row to convince myself (pretending I'm a maintainer looking at the ticket ) that there's something there.

 

[David Dyer-Bennet]

I'm capturing the traffic. It isn't informative, since the connection is encrypted. Anything I should look for in just the packet sequence? Or do I need to go configure this to pass my email password in the clear over the public internet? (ICK!) Or other ideas?

 

[Glorious1]

I don't use dreamhost so can't help there. My first troubleshooting step would be trying an unrelated email account at a different host.

Maybe your dreamhost account or at a higher level has a spam filter that is removing the emails before they are sent on.

 

[David Dyer-Bennet]

Sending the same email from my desktop email client, through the same Dreamhost server and account, and from the same IP address (like most home setups, everything at home is behind NAT), works fine, the email shows up immediately. So I don't think it's that kind of filtering.

 

[Glorious1]

Sending the same email from my desktop email client, through the same Dreamhost server and account, and from the same IP address (like most home setups, everything at home is behind NAT), works fine, the email shows up immediately. So I don't think it's that kind of filtering.

That's good, but I would still try a different email account. The client sending it plays a significant role in how it gets treated by filters I believe. Is the sending and receiving account the same?

 

[David Dyer-Bennet]

Well, I could use a different account at exactly the same server, but I can't try a different server, I don't have access to any other smtp servers. Nor do I believe there is outbound spam filtering happening that doesn't result in complaints coming to me, and no complaints have come.

 

[Glorious1]

If you're sending it to yourself, it could be inbound filtering. You really don't have another unrelated email account?

 

[David Dyer-Bennet]

INbound filtering never makes things disappear entirely without trace.

I've got many email *accounts* but all my access to SMTP sending is through one of them. Can't just telnet to some random port 25 these days!