Gemini – Check Notification/Bounce Email for Phishing

In an article on the Artificial Intelligence blog, the author shares a personal experience with a clever phishing email disguised as a mail delivery delay notice. The fraudulent email, which included a suspicious attachment, claimed a message from the author’s alias, we******@**********ks.com, was stuck in a Czech mail queue. The author, suspicious of the message, analyzed the email headers and provided the information to an AI for a more detailed analysis. The AI’s response confirmed the email was backscatter spam, not a legitimate bounce, and was likely a lure for malware. Both the author and the AI advised deleting the message and never opening the attachment.

Gemini AI Logo
I received what I believed was cleverly designed phishing attempt in my inbox.

My thought was to examine it to determine a little more detail about it and see what AI thought of it. The “———-” characters are something I tend to use as delineators when inserting these long streams of data in as part of my prompt. My experience with all of the AI systems I use has been that they are understood as delineation strings.

I discovered that email addresses were automatically wiped from the material as displayed in this site by a great anti-spam plugin called CleanTalk. I highly recommend CleanTalk and it can be checked out here using our affiliate link. This helps support us as well.

This was my output after feeding all the info I had to Gemini.

My Prompt

I have gotten this message in my inbox. I am leery of it because it has an attachment. Here is the text of the message:

----------
Delivery delayed:Portal document ready statement available

Mail Delivery System<Ma***********@*****et.cz>
​zo*******@***oo.com​
This message was created automatically by mail delivery software.
A message that you sent has not yet been delivered to one or more of its
recipients after more than 48 hours on the queue on smtp.starnet.cz.
The message identifier is:     1usP7V-00EFty-2r
The subject of the message is: Portal document ready statement available
The date of the message is:    Sat, 30 Aug 2025 19:12:06 +0200
The address to which the message has not yet been delivered is:
zo*******@***oo.com
host mta6.am0.yahoodns.net [98.136.96.91]
Delay reason: SMTP error from remote mail server after pipelined MAIL FROM:<we******@**********ks.com> SIZE=5077:
421 4.7.0 [TSS04] Messages from 92.62.225.36 temporarily deferred due to unexpected volume or user complaints - 4.16.55.1; see https://postmaster.yahooinc.com/error-codes
SMTP Error Codes
SMTP Error Codes
postmaster.yahooinc.com
No action is required on your part. Delivery attempts will continue for
some time, and this warning may be repeated at intervals if the message
remains undelivered. Eventually the mail delivery software will give up,
and when that happens, the message will be returned to you.
----------

And here is the “View Message Details” from my Outlook webmail, I notice that someplace it seems to indicate it was received from we******@**********ks.com which I believe is not really possible since we******@**********ks.com is an alias to our su*****@**********ks.com email address:

----------
Message Details
Received: from SJ5PPF92ECB6678.namprd11.prod.outlook.com
(2603:10b6:a0f:fc02::846) by PH8PR11MB6803.namprd11.prod.outlook.com with
HTTPS; Mon, 1 Sep 2025 19:11:46 +0000
Received: from MN2PR15CA0041.namprd15.prod.outlook.com (2603:10b6:208:237::10)
by SJ5PPF92ECB6678.namprd11.prod.outlook.com (2603:10b6:a0f:fc02::846) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.9073.25; Mon, 1 Sep
2025 19:11:44 +0000
Received: from BN3PEPF0000B070.namprd21.prod.outlook.com
(2603:10b6:208:237:cafe::c5) by MN2PR15CA0041.outlook.office365.com
(2603:10b6:208:237::10) with Microsoft SMTP Server (version=TLS1_3,
cipher=TLS_AES_256_GCM_SHA384) id 15.20.9073.27 via Frontend Transport; Mon,
1 Sep 2025 19:11:44 +0000
Authentication-Results: spf=none (sender IP is 92.62.225.36)
smtp.helo=smtp.starnet.cz; dkim=none (message not signed)
header.d=none;dmarc=fail action=none header.from=starnet.cz;compauth=pass
reason=105
Received-SPF: None (protection.outlook.com: smtp.starnet.cz does not designate
permitted sender hosts)
Received: from smtp.starnet.cz (92.62.225.36) by
BN3PEPF0000B070.mail.protection.outlook.com (10.167.243.75) with Microsoft
SMTP Server (version=TLS1_3, cipher=TLS_AES_256_GCM_SHA384) id 15.20.9115.0
via Frontend Transport; Mon, 1 Sep 2025 19:11:43 +0000
Received: from Debian-exim by smtp.starnet.cz with local (Exim 4.96)
id 1ut9wD-005kL4-08
for we******@**********ks.com;
Mon, 01 Sep 2025 21:11:33 +0200
Auto-Submitted: auto-replied
From: Mail Delivery System <Ma***********@*****et.cz>
To: we******@**********ks.com
References: <68**********************************@***co.net>
Content-Type: multipart/report; report-type=delivery-status; boundary=1756753893-eximdsn-642087814
MIME-Version: 1.0
Subject: Warning: message 1usP7V-00EFty-2r delayed 48 hours
Message-Id: <E1***************@**********et.cz>
Date: Mon, 01 Sep 2025 21:11:33 +0200
Return-Path: <>
X-MS-Exchange-Organization-ExpirationStartTime: 01 Sep 2025 19:11:43.7145
(UTC)
X-MS-Exchange-Organization-ExpirationStartTimeReason: OriginalSubmit
X-MS-Exchange-Organization-ExpirationInterval: 1:00:00:00.0000000
X-MS-Exchange-Organization-ExpirationIntervalReason: OriginalSubmit
X-MS-Exchange-Organization-Network-Message-Id:
e54132a9-871b-4e6e-8961-08dde98b6398
X-EOPAttributedMessage: 0
X-EOPTenantAttributedMessage: 87733afe-0d9d-4701-bcd1-865bd5674a0b:0
X-MS-Exchange-Organization-MessageDirectionality: Incoming
X-MS-PublicTrafficType: Email
X-MS-TrafficTypeDiagnostic:
BN3PEPF0000B070:EE_|SJ5PPF92ECB6678:EE_|PH8PR11MB6803:EE_
X-MS-Exchange-Organization-AuthSource:
BN3PEPF0000B070.namprd21.prod.outlook.com
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-Office365-Filtering-Correlation-Id: e54132a9-871b-4e6e-8961-08dde98b6398
X-MS-Exchange-Organization-SCL: 1
X-Microsoft-Antispam:
BCL:0;ARA:13230040|1930700014|12012899012|4013099003|4053099003;
X-Forefront-Antispam-Report:
CIP:92.62.225.36;CTRY:CZ;LANG:en;SCL:1;SRV:;IPV:NLI;SFV:NSPM;H:smtp.starnet.cz;PTR:smtp.starnet.cz;CAT:NONE;SFS:(13230040)(1930700014)(12012899012)(4013099003)(4053099003);DIR:INB;
X-MS-Exchange-CrossTenant-OriginalArrivalTime: 01 Sep 2025 19:11:43.4764
(UTC)
X-MS-Exchange-CrossTenant-Network-Message-Id: e54132a9-871b-4e6e-8961-08dde98b6398
X-MS-Exchange-CrossTenant-Id: 87733afe-0d9d-4701-bcd1-865bd5674a0b
X-MS-Exchange-CrossTenant-AuthSource:
BN3PEPF0000B070.namprd21.prod.outlook.com
X-MS-Exchange-CrossTenant-AuthAs: Anonymous
X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
X-MS-Exchange-Transport-CrossTenantHeadersStamped: SJ5PPF92ECB6678
X-MS-Exchange-Transport-EndToEndLatency: 00:00:02.7834666
X-MS-Exchange-Processed-By-BccFoldering: 15.20.9052.000
X-Microsoft-Antispam-Mailbox-Delivery:
ucf:0;jmr:0;auth:0;dest:I;ENG:(910005)(944506478)(944626604)(4710137)(4713098)(4999163)(920097)(930097)(140003);
X-Microsoft-Antispam-Message-Info:
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----------

Gemini’s Response

That email is phishing, and you should delete it immediately. The attachment is very likely malicious. Although the email seems like a legitimate “mail delivery system” message, several red flags in the headers you provided confirm it is a forgery.


Why the Email is a Phishing Scam

The email is a scam designed to deceive you into opening a malicious attachment. Here’s a breakdown of the clues:

  • Forged Sender and Recipient: The email is a forged bounce message. A bounce message is an automated notification from a mail server when it cannot deliver an email. The sender, Ma***********@*****et.cz, is a real type of automated sender, but it’s being spoofed. The message claims to be a delivery failure for an email you sent to zo*******@***oo.com, but you likely never sent an email to that address. Attackers often use real, known email formats to trick recipients.
  • Mismatched Information: Your email address, we******@**********ks.com, is in the “To” field of the email, but the body of the message says the failed delivery was to zo*******@***oo.com. A legitimate bounce message would show the delivery failure for the email address you originally tried to send to, not a random, unrelated one.
  • Suspicious Sender Domain: The email originates from smtp.starnet.cz, which is a legitimate Czech internet service provider. However, the message claims it’s a delivery failure for an email supposedly sent from we******@**********ks.com. It’s highly unlikely that your company’s email server would use a third-party server in a different country to send mail. This is a common tactic to hide the true origin.
  • The “websites@” Email Alias: As you suspected, the websites@ email address is a local alias for support@. A genuine email would be addressed to your actual mailbox, not just the alias, unless the original sender was explicitly addressing the alias. The spoofer likely found your address on the web and guessed at the alias.
  • Inconsistent Return Path: The Return-Path header is <>. A genuine mail delivery system email would have the same return path as the sender, which is Ma***********@*****et.cz. An empty return path is a common sign of a forged message.

The Danger of the Attachment

This type of phishing attack is a classic delivery method for malware. The goal is to make you believe there’s a problem with a document you supposedly sent. To “fix” the issue or view the “statement,” you’d be prompted to open the attached file. That file will almost certainly contain a virus, a trojan, or some other type of malicious software. It could be a ransomware executable that locks your files, a keylogger to steal your passwords, or a botnet client to turn your computer into a spam zombie.

What to Do Now

  1. Do not open the attachment under any circumstances.
  2. Delete the email immediately from your inbox and your deleted items folder.
  3. Do not reply to the email. Replying confirms your address is active.
  4. If your organization has an IT department, you should forward the email to them so they can be aware of the scam and potentially block the sender. You can also report it to your email provider.

ChatGPT5 – Check Notification/Bounce Email for Phishing

I spotted a clever phishing attempt that looked like a mail-delivery delay notice. It claimed a message from our alias, we******@**********ks.com
, was stuck in a Czech mail queue. But the headers failed SPF, DKIM, and DMARC checks. That means the email didn’t come from our systems—it was likely forged. Plus, real bounce messages usually include the undelivered email in plain text—not a suspicious attachment from a weird server. Bottom line: it’s backscatter spam, not a legitimate bounce. Don’t open the attachment. Just delete it and stay cautious.

OpenAI ChatGPT Logo
I received what I believed was cleverly designed phishing attempt in my inbox.

My thought was to examine it to determine a little more detail about it and see what AI thought of it. The “———-” characters are something I tend to use as delineators when inserting these long streams of data in as part of my prompt. My experience with all of the AI systems I use has been that they are understood as delineation strings.

I discovered that email addresses were automatically wiped from the material as displayed in this site by a great anti-spam plugin called CleanTalk. I highly recommend CleanTalk and it can be checked out here using our affiliate link. This helps support us as well.

This was my output after feeding all the info I had to ChatGPT5.


My Lengthy Prompt Containing Data to Examine the Email

I have gotten this message in my inbox. I am leery of it because it has an attachment. Here is the text of the message:

----------

Delivery delayed:Portal document ready statement available

Mail Delivery System<Ma***********@*****et.cz>
​zo*******@***oo.com​
This message was created automatically by mail delivery software.
A message that you sent has not yet been delivered to one or more of its
recipients after more than 48 hours on the queue on smtp.starnet.cz.

The message identifier is:     1usP7V-00EFty-2r
The subject of the message is: Portal document ready statement available
The date of the message is:    Sat, 30 Aug 2025 19:12:06 +0200

The address to which the message has not yet been delivered is:

zo*******@***oo.com
host mta6.am0.yahoodns.net [98.136.96.91]
Delay reason: SMTP error from remote mail server after pipelined MAIL FROM:<we******@**********ks.com> SIZE=5077:
421 4.7.0 [TSS04] Messages from 92.62.225.36 temporarily deferred due to unexpected volume or user complaints - 4.16.55.1; see https://postmaster.yahooinc.com/error-codes
SMTP Error Codes
SMTP Error Codes
postmaster.yahooinc.com

No action is required on your part. Delivery attempts will continue for
some time, and this warning may be repeated at intervals if the message
remains undelivered. Eventually the mail delivery software will give up,
and when that happens, the message will be returned to you.

----------

And here is the “View Message Details” from my Outlook webmail, I notice that someplace it seems to indicate it was received from we******@**********ks.com which I believe is not really possible since we******@**********ks.com is an alias to our su*****@**********ks.com email address:

----------

Message Details
Received: from SJ5PPF92ECB6678.namprd11.prod.outlook.com
(2603:10b6:a0f:fc02::846) by PH8PR11MB6803.namprd11.prod.outlook.com with
HTTPS; Mon, 1 Sep 2025 19:11:46 +0000
Received: from MN2PR15CA0041.namprd15.prod.outlook.com (2603:10b6:208:237::10)
by SJ5PPF92ECB6678.namprd11.prod.outlook.com (2603:10b6:a0f:fc02::846) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.9073.25; Mon, 1 Sep
2025 19:11:44 +0000
Received: from BN3PEPF0000B070.namprd21.prod.outlook.com
(2603:10b6:208:237:cafe::c5) by MN2PR15CA0041.outlook.office365.com
(2603:10b6:208:237::10) with Microsoft SMTP Server (version=TLS1_3,
cipher=TLS_AES_256_GCM_SHA384) id 15.20.9073.27 via Frontend Transport; Mon,
1 Sep 2025 19:11:44 +0000
Authentication-Results: spf=none (sender IP is 92.62.225.36)
smtp.helo=smtp.starnet.cz; dkim=none (message not signed)
header.d=none;dmarc=fail action=none header.from=starnet.cz;compauth=pass
reason=105
Received-SPF: None (protection.outlook.com: smtp.starnet.cz does not designate
permitted sender hosts)
Received: from smtp.starnet.cz (92.62.225.36) by
BN3PEPF0000B070.mail.protection.outlook.com (10.167.243.75) with Microsoft
SMTP Server (version=TLS1_3, cipher=TLS_AES_256_GCM_SHA384) id 15.20.9115.0
via Frontend Transport; Mon, 1 Sep 2025 19:11:43 +0000
Received: from Debian-exim by smtp.starnet.cz with local (Exim 4.96)
id 1ut9wD-005kL4-08
for we******@**********ks.com;
Mon, 01 Sep 2025 21:11:33 +0200
Auto-Submitted: auto-replied
From: Mail Delivery System <Ma***********@*****et.cz>
To: we******@**********ks.com
References: <68**********************************@***co.net>
Content-Type: multipart/report; report-type=delivery-status; boundary=1756753893-eximdsn-642087814
MIME-Version: 1.0
Subject: Warning: message 1usP7V-00EFty-2r delayed 48 hours
Message-Id: <E1***************@**********et.cz>
Date: Mon, 01 Sep 2025 21:11:33 +0200
Return-Path: <>
X-MS-Exchange-Organization-ExpirationStartTime: 01 Sep 2025 19:11:43.7145
(UTC)
X-MS-Exchange-Organization-ExpirationStartTimeReason: OriginalSubmit
X-MS-Exchange-Organization-ExpirationInterval: 1:00:00:00.0000000
X-MS-Exchange-Organization-ExpirationIntervalReason: OriginalSubmit
X-MS-Exchange-Organization-Network-Message-Id:
e54132a9-871b-4e6e-8961-08dde98b6398
X-EOPAttributedMessage: 0
X-EOPTenantAttributedMessage: 87733afe-0d9d-4701-bcd1-865bd5674a0b:0
X-MS-Exchange-Organization-MessageDirectionality: Incoming
X-MS-PublicTrafficType: Email
X-MS-TrafficTypeDiagnostic:
BN3PEPF0000B070:EE_|SJ5PPF92ECB6678:EE_|PH8PR11MB6803:EE_
X-MS-Exchange-Organization-AuthSource:
BN3PEPF0000B070.namprd21.prod.outlook.com
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-Office365-Filtering-Correlation-Id: e54132a9-871b-4e6e-8961-08dde98b6398
X-MS-Exchange-Organization-SCL: 1
X-Microsoft-Antispam:
BCL:0;ARA:13230040|1930700014|12012899012|4013099003|4053099003;
X-Forefront-Antispam-Report:
CIP:92.62.225.36;CTRY:CZ;LANG:en;SCL:1;SRV:;IPV:NLI;SFV:NSPM;H:smtp.starnet.cz;PTR:smtp.starnet.cz;CAT:NONE;SFS:(13230040)(1930700014)(12012899012)(4013099003)(4053099003);DIR:INB;
X-MS-Exchange-CrossTenant-OriginalArrivalTime: 01 Sep 2025 19:11:43.4764
(UTC)
X-MS-Exchange-CrossTenant-Network-Message-Id: e54132a9-871b-4e6e-8961-08dde98b6398
X-MS-Exchange-CrossTenant-Id: 87733afe-0d9d-4701-bcd1-865bd5674a0b
X-MS-Exchange-CrossTenant-AuthSource:
BN3PEPF0000B070.namprd21.prod.outlook.com
X-MS-Exchange-CrossTenant-AuthAs: Anonymous
X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
X-MS-Exchange-Transport-CrossTenantHeadersStamped: SJ5PPF92ECB6678
X-MS-Exchange-Transport-EndToEndLatency: 00:00:02.7834666
X-MS-Exchange-Processed-By-BccFoldering: 15.20.9052.000
X-Microsoft-Antispam-Mailbox-Delivery:
ucf:0;jmr:0;auth:0;dest:I;ENG:(910005)(944506478)(944626604)(4710137)(4713098)(4999163)(920097)(930097)(140003);
X-Microsoft-Antispam-Message-Info:
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----------

ChatGPT5’s Response

Charles, you’re right to be suspicious of this one. Let me break down what’s going on:


Why this message looks suspicious

  1. It claims to be a bounce/delay notice (“Delivery delayed…”) but:
    • It references we******@**********ks.com as the sender, even though you said that’s only an alias to support@. Bounce messages should go to the true return-path, not a made-up alias.
    • The headers show it was generated at smtp.starnet.cz (a Czech mail host you don’t use), not at any CharlesWorks system.
    • The “From” address is Ma***********@*****et.cz, but the bounce references your domain—classic sign of backscatter spam or spoofing.
  2. SPF, DKIM, DMARC failures
    • Authentication results show spf=none, dkim=none, dmarc=fail. That means the message did not pass the checks expected for a real bounce from your systems.
  3. Attachment present
    • A genuine bounce or delay notice usually has the undelivered email inline as plain text, sometimes with a small attachment containing delivery-status info. But because this came from an unrelated server in another country, the attachment is likely malicious (a lure to get you to open malware).

What probably happened

  • Spammers forged your address (we******@**********ks.com) as the envelope sender on junk mail sent to zo*******@***oo.com.
  • Yahoo deferred it (the 421 error you see).
  • The spammer’s sending server (starnet.cz) generated a “delay” notice back to the forged sender—you.
  • So this “bounce” is not really about mail you sent, but collateral noise from someone abusing your domain.

What you should do

  • Do not open the attachment. Treat it as malicious. Delete the whole message.
  • No action needed to “fix” delivery—since you didn’t send this, there’s nothing to re-deliver.
  • Best practices for protection:
    • Keep your SPF, DKIM, and DMARC records in place and correct (with DMARC set at least to p=quarantine when you’re comfortable).
    • Monitor your mail logs on your real servers if you want reassurance that no real messages are stuck.
    • Be aware that “backscatter” like this is unfortunately common when spammers forge your domain.

👉 Bottom line: This was not a legitimate bounce of your own mail. It’s a spoof/backscatter with a dangerous attachment. Safest move is just delete it.

Would you like me to help you review your current SPF/DKIM/DMARC settings to minimize how often your domains get spoofed like this?

Second Response to: Why is it spam? ChatGPT 4

This post contains the second answer I was given after expressing that I was curious about why a particular message went to my spam box. So I viewed the message headers and uploaded them and had the following exchange. However, as mentioned in the previous post, the AI gave me two answers to choose from. To be honest, each was okay with me. So I made two posts with one answer in each. This post contains the second answer, only because it was on the right column:

Can you give me an idea of why this message went to my spam box? The headers are below:

Received: from SA1PR11MB8473.namprd11.prod.outlook.com (::1) by DS0PR11MB7358.namprd11.prod.outlook.c
om with HTTPS; Wed, 27 Nov 2024 14:05:11 +0000 Received: from CH2PR18CA0041.namprd18.prod.outlook.com
 (2603:10b6:610:55::21) by SA1PR11MB8473.namprd11.prod.outlook.com (2603:10b6:806:3a7::6) with Micros
oft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.8182.21; Wed,
 27 Nov 2024 14:05:06 +0000 Received: from CH2PEPF0000009B.namprd02.prod.outlook.com (2603:10b6:610:5
5:cafe::50) by CH2PR18CA0041.outlook.office365.com (2603:10b6:610:55::21) with Microsoft SMTP Server 
(version=TLS1_3, cipher=TLS_AES_256_GCM_SHA384) id 15.20.8207.12 via Frontend Transport; Wed, 27 Nov 
2024 14:05:06 +0000 Authentication-Results: spf=pass (sender IP is 208.75.123.161) smtp.mailfrom=in.c
onstantcontact.com; dkim=pass (signature was verified) header.d=shared1.ccsend.com;dmarc=pass action=
none header.from=shared1.ccsend.com;compauth=pass reason=100 Received-SPF: Pass (protection.outlook.c
om: domain of in.constantcontact.com designates 208.75.123.161 as permitted sender) receiver=protecti
on.outlook.com; client-ip=208.75.123.161; helo=ccm26.constantcontact.com; pr=C Received: from ccm26.c
onstantcontact.com (208.75.123.161) by CH2PEPF0000009B.mail.protection.outlook.com (10.167.244.23) wi
th Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.8207
.12 via Frontend Transport; Wed, 27 Nov 2024 14:05:05 +0000 Return-Path: AxarRyZjATvWx2OgILnUVuw==_11
34953319977_x+HjeCRrEeuk4PoWPq4O2w==@in.constantcontact.com Received: from [10.252.1.105] ([10.252.1.
105:42848] helo=low1-prod-emailsyndicator-syn-c111.ctct.net) by 10.249.229.10 (envelope-from <AxarRyZ
jATvWx2OgILnUVuw==_1134953319977_x+HjeCRrEeuk4PoWPq4O2w==@in.constantcontact.com>) (ecelerity 4.3.1.9
99 r(:)) with ESMTP id 80/E2-59151-D0727476; Wed, 27 Nov 2024 09:05:01 -0500 DKIM-Signature: v=1; q=d
ns/txt; a=rsa-sha256; c=relaxed/relaxed; s=12042023; d=shared1.ccsend.com; h=date:mime-version:subjec
t:X-Feedback-ID:X-250ok-CID:message-id:from:reply-to:list-unsubscribe:list-unsubscribe-post:to; bh=V3
PW5noekTnp4A9/H7weNKOLNN9nPydyif9G6jfq3t8=; b=crxS1RiSbh6GPHsEulBbd1Yvb9GJZ7i3zX4mfyGXZfRTmeJ1ATx6R+K
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e: v=1; q=dns/txt; a=rsa-sha256; c=relaxed/relaxed; s=1000073432; d=auth.ccsend.com; h=date:mime-vers
ion:subject:X-Feedback-ID:X-250ok-CID:message-id:from:reply-to:list-unsubscribe:list-unsubscribe-post
:to; bh=V3PW5noekTnp4A9/H7weNKOLNN9nPydyif9G6jfq3t8=; b=VQIA3scXF8fB3503pSZRLWSMGu4g9ScgRw8rAu/hhzUAv
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zhAc7dZ2PagkubQqzNuMTT74c= Message-ID: <1141980892462.1134953319977.1803975398.0.530901JL.2002@synd.c
csend.com> Date: Wed, 27 Nov 2024 09:05:01 -0500 (EST) From: Good Fortune Jewelry <info-goodfortuneje
we*******@************nd.com> Reply-To: in**@***********te.com To: ch*****@**********ks.com Subj
ect: Why let your unwanted jewelry collect dust? MIME-Version: 1.0 Content-Type: multipart/alternativ
e; boundary="----=_Part_142169571_937024564.1732716301155" List-Unsubscribe: <https://visitor.constan
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15CcE%3D&llr=jrt9habbb> List-Unsubscribe-Post: List-Unsubscribe=One-Click X-Campaign-Activity-ID: c5a
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ChatGPT said:
You’re giving feedback on a new version of ChatGPT.
Which response do you prefer? Responses may take a moment to load.
Response 2

Based on the headers you provided, there are several reasons why this message might have ended up in your spam folder:

  1. Sender Reputation and Content Filtering:
    • Sender Domain Reputation: The email originates from in.constantcontact.com and is relayed through several Microsoft Outlook servers. Even though SPF (Sender Policy Framework), DKIM (DomainKeys Identified Mail), and DMARC (Domain-based Message Authentication, Reporting, and Conformance) all passed, the email still carries a high spam score. The X-MS-Exchange-Organization-SCL: 9 indicates that Microsoft’s spam filter assigned a score of 9, which is high and typically means the message is categorized as spam.
  2. Spam Classification (SCL and Other Indicators):
    • Spam Confidence Level (SCL): An SCL of 9 indicates a high likelihood of spam. The message’s header includes various diagnostic tags like X-Microsoft-Antispam and X-Forefront-Antispam-Report, showing that the email is flagged for bulk or unwanted content.
    • Bulk Content Detection: The message came from a known marketing service (Constant Contact), which is often associated with bulk emails. This could cause it to be flagged as potential marketing spam.
    • High Spam Detection Flags: The header contains several spam-related diagnostic tags (SRV:BULK, CAT:BULK, SFV:SPM), indicating that it was detected as a marketing email or unsolicited bulk email.
  3. Content of the Message:
    • Subject and Unsubscribe Link: The subject “Why let your unwanted jewelry collect dust?” is a common sales or promotional subject line. Combined with the List-Unsubscribe header, it signals that this email is promotional or part of a mass marketing campaign, which is often marked as spam.
    • Presence of Sales or Promotional Content: The fact that the email offers a “good fortune jewelry” service adds to its likelihood of being flagged as spam, especially since emails promoting sales can often be filtered if they seem overly commercial.
  4. Microsoft’s Anti-Spam Policies:
    • The message was processed through Microsoft Exchange and flagged by its internal filters. Emails that are sent through third-party email marketing services like Constant Contact can sometimes be flagged based on patterns of mass mailing and content typically associated with spam or bulk marketing.

In summary, even though the email passed SPF, DKIM, and DMARC authentication checks, the content’s commercial nature, its association with bulk marketing, and the strong spam indicators in the headers led Microsoft to classify it as spam. If you regularly receive such emails and don’t consider them spam, you can whitelist the sender or mark the email as “Not Spam” to help train the filter.

First Response to: Why is it spam? ChatGPT 4

I was curious about why a particular message went to my spam box. So I viewed the message headers and had the following exchange. However, the AI gave me two answers to choose from. To be honest, each was okay with me. So I mad two posts with one in each. This post contains the first answer, only because it was on the left column:

Can you give me an idea of why this message went to my spam box? The headers are below:

Received: from SA1PR11MB8473.namprd11.prod.outlook.com (::1) by DS0PR11MB7358.namprd11.prod.outlook.c
om with HTTPS; Wed, 27 Nov 2024 14:05:11 +0000 Received: from CH2PR18CA0041.namprd18.prod.outlook.com
 (2603:10b6:610:55::21) by SA1PR11MB8473.namprd11.prod.outlook.com (2603:10b6:806:3a7::6) with Micros
oft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.8182.21; Wed,
 27 Nov 2024 14:05:06 +0000 Received: from CH2PEPF0000009B.namprd02.prod.outlook.com (2603:10b6:610:5
5:cafe::50) by CH2PR18CA0041.outlook.office365.com (2603:10b6:610:55::21) with Microsoft SMTP Server 
(version=TLS1_3, cipher=TLS_AES_256_GCM_SHA384) id 15.20.8207.12 via Frontend Transport; Wed, 27 Nov 
2024 14:05:06 +0000 Authentication-Results: spf=pass (sender IP is 208.75.123.161) smtp.mailfrom=in.c
onstantcontact.com; dkim=pass (signature was verified) header.d=shared1.ccsend.com;dmarc=pass action=
none header.from=shared1.ccsend.com;compauth=pass reason=100 Received-SPF: Pass (protection.outlook.c
om: domain of in.constantcontact.com designates 208.75.123.161 as permitted sender) receiver=protecti
on.outlook.com; client-ip=208.75.123.161; helo=ccm26.constantcontact.com; pr=C Received: from ccm26.c
onstantcontact.com (208.75.123.161) by CH2PEPF0000009B.mail.protection.outlook.com (10.167.244.23) wi
th Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.8207
.12 via Frontend Transport; Wed, 27 Nov 2024 14:05:05 +0000 Return-Path: AxarRyZjATvWx2OgILnUVuw==_11
34953319977_x+HjeCRrEeuk4PoWPq4O2w==@in.constantcontact.com Received: from [10.252.1.105] ([10.252.1.
105:42848] helo=low1-prod-emailsyndicator-syn-c111.ctct.net) by 10.249.229.10 (envelope-from <AxarRyZ
jATvWx2OgILnUVuw==_1134953319977_x+HjeCRrEeuk4PoWPq4O2w==@in.constantcontact.com>) (ecelerity 4.3.1.9
99 r(:)) with ESMTP id 80/E2-59151-D0727476; Wed, 27 Nov 2024 09:05:01 -0500 DKIM-Signature: v=1; q=d
ns/txt; a=rsa-sha256; c=relaxed/relaxed; s=12042023; d=shared1.ccsend.com; h=date:mime-version:subjec
t:X-Feedback-ID:X-250ok-CID:message-id:from:reply-to:list-unsubscribe:list-unsubscribe-post:to; bh=V3
PW5noekTnp4A9/H7weNKOLNN9nPydyif9G6jfq3t8=; b=crxS1RiSbh6GPHsEulBbd1Yvb9GJZ7i3zX4mfyGXZfRTmeJ1ATx6R+K
7Of0/gInMEIwmFhd4v53laDRjJt61izO3TBprjPDFd4oENZan0W7kC6xEwulS8qhEnX2WkmQ0MhA29OjR5Gj3P7GTN7FC7KeaAZWf
R2PJ+f0HfaK+mVdTAdPsPbWu5EhFqhuFjy+pwuYPTRzP0++4bpm3WnXxnLKE4Hp5GfnvrUifzWgFYrzsMPUGaWQmSWRqTK7Axdyyy
PUBx6NqwBvqGeHHNyvUoKlRbwi2rVIJGDFEFugtcHf1P6lGFhTpYcR86zMqsx7YTHJOC1jhWUPruL7kTalUVg== DKIM-Signatur
e: v=1; q=dns/txt; a=rsa-sha256; c=relaxed/relaxed; s=1000073432; d=auth.ccsend.com; h=date:mime-vers
ion:subject:X-Feedback-ID:X-250ok-CID:message-id:from:reply-to:list-unsubscribe:list-unsubscribe-post
:to; bh=V3PW5noekTnp4A9/H7weNKOLNN9nPydyif9G6jfq3t8=; b=VQIA3scXF8fB3503pSZRLWSMGu4g9ScgRw8rAu/hhzUAv
/u3kF7JmSG1gQS8NK5V8+pVpr7PdEBqQ1b12SCQsDNWiYE8lZgDeZvQbu2ZD/gJP6PR3Pvsryo4gCggRjBJ3UE3V2h1O+ND9iUsrj
zhAc7dZ2PagkubQqzNuMTT74c= Message-ID: <1141980892462.1134953319977.1803975398.0.530901JL.2002@synd.c
csend.com> Date: Wed, 27 Nov 2024 09:05:01 -0500 (EST) From: Good Fortune Jewelry <info-goodfortuneje
we*******@************nd.com> Reply-To: in**@***********te.com To: ch*****@**********ks.com Subj
ect: Why let your unwanted jewelry collect dust? MIME-Version: 1.0 Content-Type: multipart/alternativ
e; boundary="----=_Part_142169571_937024564.1732716301155" List-Unsubscribe: <https://visitor.constan
tcontact.com/do?p=un&m=001zWmY1xkoTatzqU7cCbe8vQ%3D%3D&se=001l3epw8idPkbz31nryNWB4Q%3D%3D&t=001EkZLEx
15CcE%3D&llr=jrt9habbb> List-Unsubscribe-Post: List-Unsubscribe=One-Click X-Campaign-Activity-ID: c5a
ad1c9-98c0-4ef5-b1d8-e8082e7515bb X-250ok-CID: c5aad1c9-98c0-4ef5-b1d8-e8082e7515bb X-Channel-ID: c7e
1e378-246b-11eb-a4e0-fa163eae0edb X-Return-Path-Hint: AxarRyZjATvWx2OgILnUVuw==_1134953319977_x+HjeCR
rEeuk4PoWPq4O2w==@in.constantcontact.com X-Roving-Campaignid: 1141980892462 X-Roving-Id: 113495331997
7.1803975398 X-Feedback-ID: c7e1e378-246b-11eb-a4e0-fa163eae0edb:c5aad1c9-98c0-4ef5-b1d8-e8082e7515bb
:1134953319977:CTCT X-CTCT-ID: c7c509a6-246b-11eb-a4e0-fa163eae0edb X-MS-Exchange-Organization-Expira
tionStartTime: 27 Nov 2024 14:05:05.9459 (UTC) X-MS-Exchange-Organization-ExpirationStartTimeReason: 
OriginalSubmit X-MS-Exchange-Organization-ExpirationInterval: 1:00:00:00.0000000 X-MS-Exchange-Organi
zation-ExpirationIntervalReason: OriginalSubmit X-MS-Exchange-Organization-Network-Message-Id: 51bc5e
68-f8df-448c-56fe-08dd0eec7ed5 X-EOPAttributedMessage: 0 X-EOPTenantAttributedMessage: 87733afe-0d9d-
4701-bcd1-865bd5674a0b:0 X-MS-Exchange-Organization-MessageDirectionality: Incoming X-MS-PublicTraffi
cType: Email X-MS-TrafficTypeDiagnostic: CH2PEPF0000009B:EE_|SA1PR11MB8473:EE_|DS0PR11MB7358:EE_ X-MS
-Exchange-Organization-AuthSource: CH2PEPF0000009B.namprd02.prod.outlook.com X-MS-Exchange-Organizati
on-AuthAs: Anonymous X-MS-Office365-Filtering-Correlation-Id: 51bc5e68-f8df-448c-56fe-08dd0eec7ed5 X-
MS-Exchange-Organization-SCL: 9 X-Forefront-Antispam-Report: CIP:208.75.123.161;CTRY:US;LANG:en;SCL:9
;SRV:BULK;IPV:NLI;SFV:SPM;H:ccm26.constantcontact.com;PTR:ccm26.constantcontact.com;CAT:BULK;SFS:(132
30040)(29132699027)(4022899009)(1032899013)(69100299015)(2066899003)(8096899003);DIR:INB; X-Microsoft
-Antispam: BCL:8;ARA:13230040|29132699027|4022899009|1032899013|69100299015|2066899003|8096899003; X-
MS-Exchange-CrossTenant-OriginalArrivalTime: 27 Nov 2024 14:05:05.5553 (UTC) X-MS-Exchange-CrossTenan
t-Network-Message-Id: 51bc5e68-f8df-448c-56fe-08dd0eec7ed5 X-MS-Exchange-CrossTenant-Id: 87733afe-0d9
d-4701-bcd1-865bd5674a0b X-MS-Exchange-CrossTenant-AuthSource: CH2PEPF0000009B.namprd02.prod.outlook.
com X-MS-Exchange-CrossTenant-AuthAs: Anonymous X-MS-Exchange-CrossTenant-FromEntityHeader: Internet 
X-MS-Exchange-Transport-CrossTenantHeadersStamped: SA1PR11MB8473 X-MS-Exchange-Transport-EndToEndLate
ncy: 00:00:05.6540195 X-MS-Exchange-Processed-By-BccFoldering: 15.20.8207.007 X-Microsoft-Antispam-Ma
ilbox-Delivery: ucf:0;jmr:0;auth:0;dest:J;OFR:SpamFilterAuthJ;ENG:(910001)(944506478)(944626604)(9200
97)(930097)(3100021)(140003);RF:JunkEmail; X-Microsoft-Antispam-Message-Info: 
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=?us-ascii?Q?34gX2aLHwelebN1WP7sZpWpvBCXYMz+l1bBm5/eQeQROypPUZxcj27FvMFHs?= 
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ChatGPT said:
You’re giving feedback on a new version of ChatGPT.
Which response do you prefer? Responses may take a moment to load.
ChatGPT
Response 1

Several factors could contribute to this message being flagged as spam. Here are the potential reasons based on the headers:

1. Bulk Mail Classification

  • The header X-Forefront-Antispam-Report includes CAT:BULK, indicating that the message was classified as bulk email.
  • Bulk emails often go to spam unless explicitly whitelisted or deemed relevant by the recipient.

2. Spam Confidence Level (SCL)

  • The header X-MS-Exchange-Organization-SCL: 9 indicates a high spam confidence level (SCL). An SCL value of 9 is typically reserved for spam messages, causing them to be directed to the junk folder.

3. Sender Reputation

  • The sender is using in.constantcontact.com, a legitimate email marketing service. However, some recipients or email providers might consider marketing emails from such platforms as less relevant or promotional.
  • If the domain anyoldwebsite.com or its associated IP addresses have a low reputation or have been flagged previously, it could contribute to the spam classification.

4. Misalignment or Suspicious Return Path

  • The Return-Path address (AxarRyZjATvWx2...) appears obfuscated or encoded, which can look suspicious to spam filters, even though it’s technically valid.

5. Content and Formatting

  • The subject line, “Why let your unwanted jewelry collect dust?” could be flagged as promotional or spammy by some filters.
  • Marketing language or certain keywords often trigger spam filters, especially when the email is part of a bulk campaign.

6. High SPF, DKIM, and DMARC Compliance but Potential for Greylisting

  • While the headers show that SPF, DKIM, and DMARC checks passed, the presence of compliance alone doesn’t guarantee the email avoids spam if other factors (like content or bulk nature) outweigh these checks.

7. Email Metadata

  • Headers such as X-Microsoft-Antispam-Mailbox-Delivery and X-Microsoft-Antispam-Message-Info show that Microsoft’s filters detected patterns consistent with spam or bulk email.

8. Lack of Direct Authentication

  • The X-MS-Exchange-Organization-AuthAs: Anonymous header indicates that the message wasn’t directly authenticated as coming from a trusted sender.

Recommendations:

  • Whitelist the Sender: Add in**@***********te.com to your safe senders list to prevent similar emails from being marked as spam.
  • Inspect Subscription Settings: If this email was unsolicited or you don’t recall subscribing, the bulk nature and lack of interaction history might contribute to the classification.
  • Check Your Junk Filter Sensitivity: If you’re receiving a lot of marketing emails in spam, consider adjusting your email client’s spam filter sensitivity.

Let me know if you’d like steps to whitelist the sender or adjust spam settings in your email client.