Mailing List ecs-isp@2rosenthals.com Archived Message #1177

From: "Lewis G Rosenthal" <ecs-isp@2rosenthals.com> Full Headers
Undecoded message
Subject: Re: [eCS-ISP] Trouble getting mail delivered to Office365 (outlook.com), ProofPoint, and Barracuda protected domains
Date: Wed, 23 Apr 2025 15:03:47 -0400
To: eCS ISP Mailing List <ecs-isp@2rosenthals.com>

Hi, Max...

On 04/23/25 01:28 pm, Massimo S. wrote:
Il 22/04/2025 22:50, Lewis G Rosenthal ha scritto:
Hi, all...

For the past few days, I've been dealing with an issue of mail from 2rosenthals.com apparenly getting blackholed by certain providers. We do not receive any kind of DSN. From all accounts, the email is going out for delivery and that's that. However, on the other end, recipients aren't seeing the messages, nor are they getting any kind of spam notification or other warning that a message could not be delivered.

Affected domains seem to be hosted with a handful of providers, Office365 among them, which uses outlook.com. Naturally, I've checked both the outlook.com and live.com internal lists, and both show that neither of our IPs is listed.

Other MXs which seem to be behaving similarly are:

gpphosted.com (ProofPoint)
barracudanetworks.com

Multiple multiple-RBL checks come up clean for both IPs and our domain. SPF, DKIM, and DMARC configurations all look fine (read: pass specific checks by various third parties, including mxtoolbox.com).

Mail flows without incident to gmail.com and yahoo.com.

Is anyone else seeing anything like this?

TIA

Hi Lewis,

yes, since i use Weasel as MTA and some european domain is start to refusing SMTP plain,
they only accept STARTTLS.

Anyway Peter plans to add TLS in the next months.

Here i had to use external SMPTs as intermediary SMTP to keep on receiving emails
from this domain.


STARTTLS has been enabled at the firewall for years, requiring a minimum of TLS v1. I just bumped that up to 1.2, in case that was some cause for concern (though I don't see why; negotiation always takes place at the highest level agreed upon by both parties).

I've also disabled outbound AV and spam scanning (I already added affected domains to the list to skip adding the "Scanned by..." footer), just to exclude any additional headers which may be misconstrued.

So far, no positive results sending to domains hosted behind outlook.com (and I have not re-tested the others, as yet, except to confirm that we are getting through Barracuda's scanners).

--
Lewis
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Lewis G Rosenthal, CNA, CLP, CLE, CWTS, EA
Rosenthal & Rosenthal, LLC                www.2rosenthals.com
visit my IT blog                www.2rosenthals.net/wordpress
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