iMac Ventura: Mail sends messages to unintended recipients

On my iMac (macOS Ventura), I tried to “share” a recorded iPhone conversation from Notes by emailing it from one of my Apple addresses to another. This is what happened:


At 18:03h EST I send my test email, without the recording that should have automatically been attached, from one Apple address (@me.com) to another (@icloud.com).


At 18:04h, the iCloud Mail Delivery System returned the message to Sender: “This is a system-generated message to inform you that your email could not be delivered to one or more recipients. Details of the email, etc.” — from mailer-daemon@icloud.com.


At 18:04h, my message was bounced as Undeliverable by postmaster@adobe.com. Why is Adobe bouncing an email sent from one apple email address to another? (See screenshot below.) “Info for Email Admins,” an exploded message header and a table of Message Hops follows. cclresearch@adobe.com mention a “message loop.”  I’m beginning to suspect that Mail, for reasons way above my pay grade, spontaneously grabbed email addresses from my Contacts and sent copies of the test email to them. 


At 18:12h, I get another “Undelivered Mail Returned to Sender” message from mailer-daemon@icloud.com:  “<xxxxxxxxx@me.com>: Message delivery failed,” followed by the exploded code of the message I did not (intend to) send to a physical therapy outfit I haven’t used for five years.


At 18:15h, I get an email from Wired Magazine Customer Service thanking me for contacting their fulfillment department. Needless to say, I did NOT send them any such email.


Is macOS Mail melting down, or does sending a Mail message from a (@me.com) address to an (@icloud.com) address cause the IMAP/SMTP servers to melt down?  Did I accidentally drop a bomb into something? What on earth happened?




[Edited by Moderator]

Earlier Mac models

Posted on Jul 24, 2025 04:32 PM

Reply
6 replies

Jul 25, 2025 06:11 AM in response to MrHoffman

Only the single test message sent 07.24.2025 at 18:03h was in the Sent folder. Here is the raw source, PID redacted:


From: XXXXX XXXXX <xxxxxxx@me.com>

Content-Type: multipart/alternative;

boundary="Apple-Mail=_DBD5CDED-240A-xxxx-89A8-993AAB41BFA0"

Mime-Version: 1.0 (Mac OS X Mail 16.0 \(3731.700.6.1.11\))

Subject: xxxxxxx

X-Universally-Unique-Identifier: F4F028CF-A4E1-xxxx-BF5C-274BD05FF074

Message-Id: <B6E56C56-1AAA-XXXX-BC79-B7C441D8D2AB@me.com>

Date: Thu, 24 Jul 2025 18:03:24 -0400

To: "Apple @me.com" <xxxxxxx@me.com>


--Apple-Mail=_DBD5CDED-240A-xxxx-89A8-993AAB41BFA0

Content-Transfer-Encoding: 7bit

Content-Type: text/plain;

charset=us-ascii


Subject


--Apple-Mail=_DBD5CDED-240A-4xxxx-89A8-993AAB41BFA0

Content-Transfer-Encoding: 7bit

Content-Type: text/html;

charset=us-ascii


<html><head><meta http-equiv="content-type" content="text/html; charset=us-ascii"></head><body style="overflow-wrap: break-word; -webkit-nbsp-mode: space; line-break: after-white-space;"><div><p style="margin: 0.0px 0.0px 0.0px 0.0px"><font face="Helvetica Neue" size="5" style="font: 20.0px 'Helvetica Neue'"><b>250724 Subject 17:53h</b></font></p>

<p style="margin: 0.0px 0.0px 0.0px 0.0px; font: 13.0px 'Helvetica Neue'; min-height: 15.0px"><br></p>

</div></body></html>

--Apple-Mail=_DBD5CDED-240A-xxxx-89A8-993AAB41BFA0--

Jul 25, 2025 06:42 AM in response to MrHoffman

FYI, at 05:25h EST I received another “Customer Support” response (from a fan manufacturer in my Contacts) to an email I never sent to them.


I have scoured the Sent folders, Junk, Trash, on my Mac and on iCloud. There is no sign of outgoing phantom emails to Adobe, the physical therapy people or the fan manufacturer.


I do not back up my Contacts — on the iMac or on my iPhone Xr — to iCloud. There are no Contacts on iCloud now.

Jul 25, 2025 01:47 PM in response to MrHoffman

I have accidentally misled you. When I referred to "an email I never sent to them,” I meant “an email I never addressed to that recipient.”  The “Undeliverable” bounces and all the replies from unintended recipients relate to the same test message sent at 18:03h on 07/24/2025 from one Apple email address to a different Apple address — both of which belong to my Apple ID.  I may get a few more replies from unintended recipients, and there might be many more unintended recipients who won’t reply when they see that the message was not addressed to them.  No other outgoing messages to or from any of my Apple addresses are involved.


I’m very sorry that your time and effort were wasted because I wasn’t appropriately precise.


I wrote to the (unintended) recipients who replied asking them to send me the message they received because I didn’t address/send it to them, etc. I hope the raw sources contain routing histories that explain what happened.

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iMac Ventura: Mail sends messages to unintended recipients

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