From: "Massimo S." <ecs-isp@2rosenthals.com>
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Reply-To: ml@ecomstation.it
Subject: Re: [eCS-ISP] Trouble getting mail delivered to Office365
 (outlook.com), ProofPoint, and Barracuda protected domains
To: eCS ISP Mailing List <ecs-isp@2rosenthals.com>
References: <list-12871091@2rosenthals.com> <list-12900064@2rosenthals.com>
 <list-12900221@2rosenthals.com>
Organization: Massimo S.
Message-ID: <1b48e36a-3045-2ea9-0092-2ab40bb10b9b@ecomstation.it>
Date: Thu, 24 Apr 2025 09:17:30 +0200
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Il 23/04/2025 21:03, Lewis G Rosenthal ha scritto:
> 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).

that's strange

here my emails sent to my outlook account or to other ppl/firms emails using 365
arrive directly into the inbox folder

i had an issue in the past that they were being put in the spam folder
since i had a problem the reverse zone on bind

anyway there is an MS website to test this kind of issues that may help you

https://testconnectivity.microsoft.com/tests/O365InboundSmtp/input


massimo