When I send mails using Hide My Email, it gets rejected

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Level 1

49 points

When I send mails using Hide My Email, it gets rejected

Whenever I send a mail using the Hide My Email option in the From field, it gets bounced on the receiving end with the message quoted below. It happens without exception, regardless of the receiver's address or domain. This only happens when sending from the Mail app on the Mac. Mail apps on my iPad and iPhone do not present this problem and are received correctly. I have all the latest OS versions on all my devices and I'm logged on with same Apple Id on all.

Anybody knows what the reason might be?

Rejection message example:

pv37p00im-ztdi11090501.me.com rejected your message to the following email addresses:

Receiver_Name

Your message wasn't delivered because the destination email system rejected your message for security or policy reasons. For example, the email address might only accept messages from certain senders, or it might not accept certain types of messages, like those larger than a specific size.

Contact the recipient (by phone, for example) and work with them and their email admin to determine what policy or setting blocked your message and what you should do to make sure that future messages from you won't be rejected.

For more information, see Status code 5.7.1.

pv37p00im-ztdi11090501.me.com gave this error:

Delivery not authorized

-----[message headers I omit here to save space]----

Action: failed

Status: 5.7.1

Diagnostic-Code: smtp;550 5.7.1 Delivery not authorized

[Email Edited by Moderator]

Mac mini

Posted on Apr 1, 2023 04:13 PM

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Answer 1

karina184

Community Specialist

Apr 5, 2023 01:33 PM in response to Jerry_D

Hey Jerry_D,

We'll be happy to help out! Since this is only happening with the Mac, we recommend you try performing those actions to see if you have the same response in safe mode. After testing, go ahead and restart normally and test again because sometimes just starting in this mode and and then restarting normally can resolve issues: How to use safe mode on your Mac.

If your issue persists in safe mode, please follow this article in creating a new user to test and see if the issue is resolved there: Set up users, guests, and groups on Mac. This can help tell us if the issue is related to certain settings in your account conflicting with the Mail app.

Keep us updated!

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Answer 2

Rigo_O86

Community Specialist

Apr 9, 2023 04:52 PM in response to Jerry_D

Hi Jerry_D,

The issue you're describing seems to be isolated to the Mail app configuration for your user on your Mac.

What do you find when you check the outgoing mail settings on your Mac?

Here is where to look:

Change Outgoing server settings in Mail on Mac

Thanks for using the Apple Support Communities.

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Answer 3

Jerry_D Author

Level 1

49 points

Apr 9, 2023 06:27 AM in response to karina184

Hi Karina184,

Thanks a lot for your kind help.

The problem remains the same in safe mode. With a new user Mail works fine and the messages sent from Hide My Email arrive correctly. I tried with two new users, one standard and one admin, just in case. With both of those new users all works fine.

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Answer 4

Jerry_D Author

Level 1

49 points

Apr 10, 2023 03:33 AM in response to Rigo_O86

Hi Riggo_O86,

Thanks a lot for your kind support.

It does indeed look that something is different for this particular user. However, the SMTP settings are not my primary suspect because those (and absolutely all other mail settings) are identical in the three users I tested this with and I only get the problem with the original user. Still, you are pointing in the right direction as I'll explain a bit later.

I have 6 email accounts set up. Two are Exchange and two are Gmail where you do not actually see the SMTP servers added to the list that you get in Mail > Settings > Accounts > Server Settings > outgoing Account pop-up menu > Edit SMTP Server List. The remaining two are IMAP accounts on Namecheap Privateemail and those are the only ones producing the SMTP server on that list. But, as I said, all that is identical for all three users.

But you are right that something does happen with the system's behind the scenes choice of the outgoing server. My Forwarding Address in Hide My Email is the same address used as Apple Id, as Microsoft Id and is also one of those Privateemail IMAP addresses; let's call it name at mydomain.com (can't write the proper format because this forum does not allow it). Now, that being the same on the three tested users, only in the offending user's Mail does Apple choose Microsoft Exchange as the outgoing server. I know that because the rejection message comes from the outlook.com domain.

On the problematic user, if I change the Forwarding Address in Hide My Email to any of the other 5 addresses (including the two Microsoft Exchange ones), all works fine. Perhaps in the problematic setup Apple is trying to use the Microsoft outgoing server with the user name at mydomain.com but with the password of that same user for the Privateemail IMAP account.

In any case, the question remains why, all else being equal, this only happens with one user and not the other two.

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Answer 5

mingoslkd

Community Specialist

Apr 10, 2023 10:41 AM in response to Jerry_D

Hi Jerry_D,

You've done some great troubleshooting to isolate the issue. At this point, we'd advise to contact Apple Support, so they can take a closer look at why/how this is happening. Make sure to let them know what you've isolated the issue to so far.

Get Support

Take care!

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When I send mails using Hide My Email, it gets rejected

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