Forwarding with Smart Host: Page 2 - Enhance Control Panel

Forwarding with Smart Host

btraill

Any chance you know why after changing my Smarthost -- my outbound mail is still going through the previously configured smarthost? The new smarthost shows in Enhance's platform settings.

Does it take time for this change to 'propogate'?

nqnoc

btraill Try to save again.

btraill

nqnoc I've saved it a few times now -- no change in behaviour 🙁

I've also performed a graceful restart of the e-mail role. I know the new smarthost works as using it in the "System Emails" section, and performing a test email with it does indeed work.

Edit: I am... an idiot. I totally forgot about the smart host settings also being declared within the "Email Settings" of the E-mail role server itself. Those were still using my previous smart host.

I had assumed the global setting was evaluted above all.

btraill

Mailbaby seems to be working/handling forwards better than Postmark. Having said that -- I'm now seeing my WordPress form submissions failing with a 550 This message was classified as rSPAM.

I have my SPF configured and Enhance's DKIM verified. Any ideas? I've used mail-tester.com and received a 10/10 across the board. Issue is isolated to just a WordPress form submission.

josedieguez

btraill
check SPF
check the bounce URL sent by mailbaby to the sender, it usually will tell you why.
last, you can open a ticket with interserver to check the reason

PDudeP

btraill I had the same problem. Just create the server's hostname (on the server the WordPress is), so the server has its own DNS zone, and then configure SPF there .

edit: and also the Helo Name

btraill

PDudeP Ah, I didn't think about that. I only had the SPF record on the root domain. I will try that today!

Thanks all for the suggestions. I really appreciate it.

Edit: I've configured the SPF record on the actual App/DB server hosting the website, as-well as set the HELO name on that same server to the hostname that resolves back to my mail server. I'm unfortunately still seeing a 550 This message was classified as rSPAM and may not be delivered.

PDudeP

The HELO on the App/DB server, AFAIK, should be the same as the rDNS of the server's IP.
Also, you changed the SPF record, so give if a couple of hours for propagation.

btraill

PDudeP Ah, ok -- the description for HELO seems a bit misleading. It explicitly states to use the mail servers. I don't have an rDNS setup on my App/DB server. Let me do that and switch the HELO name away from the mail servers rDNS hostname.

I can see that some of my forwarded messages are dropping for spam aswell now... Appears to be picking up a bulk of the spam score from tests like:

"From and Auth And Replyto Do Not Match"
"From Neq Envfrom"
"MB Base Diff Rpto"
"Neural Spam"
"New User"

Not sure how some of these can even be addressed since that's the nature of the forwarding...

As for the contact submissions -- it looks like it's racking up spam score related to subject lines, and content. (common subject names for spam, and being flagged as suspicious content) I'm going to re-work the subject line created by the contact form submission to see if that improves anything.

Have a ticket in with MailBaby/InterServ as-well.

btraill

Update: Mailbaby support made some tweaks and now the form submissions are successful. Having said that, they are ending up in junk. (Please note they only end up in junk from the Wordpress form submission -- using the SMTP plugins "Test email" functionality delivers the email perfectly).

I can see in the mail logs it's saying to "Add header". (No authenticated sender) Scratching my head...

I would have thought the Test Email functionality in the plugin and wordpress form submission would both utilize the same sending mechanism/mail() function. Perhaps I am wrong.

mendozal

btraill I usually install this plugin to setup global Wordpress SMTP settings

https://wordpress.org/plugins/wp-mail-smtp/

Also, when I setup my contact form, I just tell it to send using the default Wordpress settings.

btraill

mendozal More progress! After removing the contact submission config, and simply relying on the config in the SMTP plugin -- it's now passing as a clean email through Mailbaby. By supplying info to the contact form actions itself -- it must have been creating the header differently. Having said all this, the email is STILL landing in my Junk folder 🙁 I cannot win here!

Forcing me to increase the Spambox setting on Mailboxes in Enhance up to about 6-8 as opposed to 4.

mendozal

btraill maybe you can whitelist that address just for this case

btraill

mendozal I'm afraid I might have to. I was really trying to prevent this type of configuration.

@slimx @mendozal Have you two inspected forwarded mail going over mailbaby to see the spam score? I can see that I'm getting hit for a number of things that just seem natural to forwarding. Is your spam score also >8-10? (Viewable from Mail Logs and then clicking the Mail ID)

mendozal

btraill 3.75 Clean

btraill

mendozal Blah... I'm at a loss.

https://ibb.co/XYnpLMT

If I run rspamc from the mail server itself to evaluate the mail file and see what rules it evaluated, the spam score is lower than the spam score from the Mailbaby relay log.

root@tt-mail:/var/local/enhance/email/mailboxes/391cff31-7bdc-4f6c-a59c-f18be088ca78/president@example2.org/mail/.Spam/cur# rspamc -h localhost < '1728078026.M911793P806997.tt-mail,S=4221,W=4305:2,S'
Results for file: stdin (0.656 seconds)
[Metric: default]
Action: add header
Spam: true
Score: 4.20 / 8.00
Symbol: ARC_ALLOW (-1.00)[mailbaby.net:s=detka:i=1]
Symbol: DMARC_NA (0.00)[example2.org]
Symbol: FROM_EQ_ENVFROM (0.00)
Symbol: FROM_HAS_DN (0.00)
Symbol: HAS_PHPMAILER_SIG (0.00)
Symbol: HAS_REPLYTO (0.00)[brad@example.com]
Symbol: MID_RHS_MATCH_FROM (0.00)
Symbol: MIME_HTML_ONLY (0.20)
Symbol: MIME_TRACE (0.00)[0:~]
Symbol: PREVIOUSLY_DELIVERED (0.00)[president@example2.org]
Symbol: RCPT_COUNT_ONE (0.00)[1]
Symbol: RCVD_COUNT_THREE (0.00)[3]
Symbol: RCVD_IN_DNSWL_LOW (-0.10)[64.20.38.26:received]
Symbol: RCVD_NO_TLS_LAST (0.10)
Symbol: RCVD_VIA_SMTP_AUTH (0.00)
Symbol: REPLYTO_DOM_NEQ_FROM_DOM (0.00)
Symbol: R_DKIM_NA (0.00)
Symbol: SPAM_FLAG (5.00)
Symbol: TO_DN_NONE (0.00)
Symbol: TO_DOM_EQ_FROM_DOM (0.00)
Message-ID: 4MEXB9zhgFGrri9kwBbUbuhSmGBUtAAe7aKojBK4@example2.org
Urls: []
Emails: ["brad@example.com"]

ChatGPT suggests the main reason is:

Why it’s Flagged as Spam:
SPAM_FLAG (5.00) is the main reason. This suggests that some internal filtering rule or past training labeled this type of email as suspicious.

Update: Mailbaby support confirmed it’s the SPAM Flag score of 5 that is the issue. This is being done before it reaches the relay via outbound spam filtering. Do you have your outbound spam filter disabled in Enhance?

I've run a recursive grep on /etc/rspamd on my mail server to try and understand the config of this check and cannot find any config files declaring the SPAM_FLAG rule. 🙁

Edit: Ever after disabling outbound spam filtering -- no change. SPAM_FLAG still being set before reaching the relay.

I've put a ticket in with Enhance. @mendozal Thank you so much for the time you've spent assisting.

mendozal

@btraill which test is failing?

btraill

For transparency/what solved this issue:

It was infact due to the From Email and the To Email not matching. I changed my configuration/flow a bit and ended up sending and receiving both with contact@domain.com and then setup a forward on contact@domain.com to president@domain.com. No spam flag being set now.

Special thanks to everyone who assisted throughout this thread.

Also, very big shoutout to John @ InterServer/MailBaby. He went above and beyond my $1/mo relay to help troubleshoot the issue which was ultimately outside of their infra.

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