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macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
I can send email using a randomly created "Hide My Email" address, or one I've already used sending to one of my other addresses, but I can't reply to them using Mail.app in Monterey 12.2.1 🤔

something went wrong.png
 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
So am I getting this right - you are trying to reply to yourself?

Perhaps that’s not supported. Why would you want to do that?

What’s your mail provider? iCloud?
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
So am I getting this right - you are trying to reply to yourself?

Perhaps that’s not supported. Why would you want to do that?

What’s your mail provider? iCloud?
No, of course not.

I'm trying to reply to email from a company to whom I gave a "Hide My Email" address to.

When I click on "Reply" I get the usual new mail including the quoted original message, but the recipient's address, and my "Hide My Email" address are greyed out, but I can type my reply.

When I attempt to send I get the message in my screenshot.

I mentioned sending to myself only to show that smtp @ iCloud is working.
 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
Ok, I see.

No idea then why this doesn’t work. Used to work here. I’ll test it again later.
 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
Okay, trying to send an email to one of my "Hide my email" addresses (as listed in my account https://appleid.apple.com/account/manage/section/privacy), I can send it out, but I instantly receive a mail delivery failure report:

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of
its recipients. This is a permanent error.

The following address failed:

4u8zxxxxxxxxxp24ay@privaterelay.appleid.com:
SMTP error from remote server for RCPT TO command, host: smtp1.privaterelay.appleid.com (17.57.152.15) reason: 550 5.1.1 Relay not allowed

?!?
 
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Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
That's odd, seems like a completely different problem!

Where are you sending it from?

Your Apple ID address or something else?

I was sending from another email address to the relay address.

Not sure if that’s a completely different problem. Maybe another symptom of the same problem?
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
I was sending from another email address to the relay address.

Not sure if that’s a completely different problem. Maybe another symptom of the same problem?
Well, it's odd that the error message you received talked about @privaterelay.appleid.com

All the headers from addresses I've sent and received include @icloud.com and lines like "Received: from st4xxxxxxxxxxxxxxx.me.com (st4xxxxxxxxxxxxxxx.me.com"

I don't think that "the relay address" (whatever@privaterelay.appleid.com) is the same as a whatever@icloud.com or whatever@me.com address.

Are you using Mail.app under Monterey?

If so what happens if you send to your other address using a new, randomly generated "Hide my email" address, then reply to that mail from your own address back to the new "Hide my email" address?
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
I was sending from another email address to the relay address.

Not sure if that’s a completely different problem. Maybe another symptom of the same problem?
"Private Relay" and "Hide my email" are two different things:

 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
"Private Relay" and "Hide my email" are two different things:
Explain that to Apple, please. This email address had been generated when I selected to “hide my email”.

Other generated email addresses do not contain the privaterelay part though. No idea about the logic behind it.
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
Explain that to Apple, please. This email address had been generated when I selected to “hide my email”.
Well, Apple has already explained it to us. Private Relay protects our internet connection via Safari using two servers. The first being Apple's and the second being CloudFlare or Akamai.

Hide my email protects our email via Apple's own mail servers: pop and smtp .icloud.com

Other generated email addresses do not contain the privaterelay part though. No idea about the logic behind it.
How did you generate that address and how are you generating those other email addresses?

Mail.app or https://appleid.apple.com ?

🤔
 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
You should either generate a new hide my email address in Mail.app directly in the "from" field of a new email, or in System Preferences --> Apple ID --> Hide my email (options).
Sorry, I didn't have time to test this earlier.

Under System Preferences --> Apple ID --> Hide my email (options), I have several email addresses listed. Some are @icloud.com, and some are @privatrelay.appleid.com. The origin of the @privatrelay.appleid.com addresses is always "Login with Apple", while the @icloud.com are labelled "Safari". I added one manually as you suggested, and its origin is now "Preferences". If I send an email to that address, I do receive it as expected.

However, I cannot generate a new one from Mail nor use the manually added one in the from field. If I select "Hide my email" in the from field, a requester pops up telling me to change the "forward to" email address in my "Hide my email" preferences. Here I'm lost, as I don't understand what Mail wants me to do.
 

Ruggy

macrumors 65816
Jan 11, 2017
1,021
665
Under your Apple id settings you should see 'contactable at' and that will have all the emails you can use with your Apple id and imessage, telephone numbers etc.
'Forward to' is telling you to forward it to one of those addresses and you should have options for that at the bottom of the 'Hide my' preferences where you should also see what it's currently sending it to.
Hide my and Relay are two totally different tabs however so maybe you set this email up using the wrong one?
I don't think hide my uses any addresses which say private relay.
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
Under your Apple id settings you should see 'contactable at' and that will have all the emails you can use with your Apple id and imessage, telephone numbers etc.

That's in System Preferences --> Apple ID --> Name, Phone, Email

'Forward to' is telling you to forward it to one of those addresses and you should have options for that at the bottom of the 'Hide my' preferences where you should also see what it's currently sending it to.

Correct

I don't think hide my uses any addresses which say private relay.

I'm puzzled by that too...
 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
Under your Apple id settings you should see 'contactable at' and that will have all the emails you can use with your Apple id and imessage, telephone numbers etc.
Thanks. Turned out that the forward address was not configured in Mail, because it’s an alias. I added it, and then everything worked.

Hide my and Relay are two totally different tabs however so maybe you set this email up using the wrong one?
I don't think hide my uses any addresses which say private relay.

Well, yes, but still I’d expect that emails sent to those addresses should be forwarded to my mail account, too, shouldn’t they? Otherwise I wouldn’t know what they’re here for.
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
Well, yes, but still I’d expect that emails sent to those addresses should be forwarded to my mail account, too, shouldn’t they? Otherwise I wouldn’t know what they’re here for.

I'm puzzled as to how you created hide my email addresses in https://appleid.apple.com/

AFAIK you can only do that in System Preferences, Mail, Safari, or https://www.icloud.com/settings/ --> Hide My Email (Manage)

I added one manually as you suggested, and its origin is now "Preferences". If I send an email to that address, I do receive it as expected.

Surely that should be "From Settings"?
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
I was referring to what is stated as the origin of the “hide my email” address in the email list in the preferences.

Sorry for causing any misinterpretations.

I was referring to that too. If I create a new Hide My Email address in System Preferences it's stated as "From Settings", not "Preferences". 🤔
 

TriciaMacMillan

macrumors 6502
Nov 10, 2021
251
149
Well, I'm glad we've helped TriciaMacMillan find a solution to her problem, but I'm still no closer to solving mine...
Well, I originally did this to try if I can reproduce your problem. Well, I can't. Replying to an email that was sent to a "hide my email" address worked.

I was referring to that too. If I create a new Hide My Email address in System Presences it's stated as "From Settings", not "Preferences". 🤔
As I'm translating back to English, the wording might be a bit different, but I think we're speaking of different things:
  • If I create the email by adding it through Preferences > Apple ID > Hide my email, then it's labeled "Preferences"
  • If I create the email by selecting "Hide my email" in the From field in the Mail app, then it's labeled "Mail"
 

Unsupported

macrumors 6502a
Original poster
Jul 23, 2020
706
752
a land far, far away...
Well, I originally did this to try if I can reproduce your problem. Well, I can't. Replying to an email that was sent to a "hide my email" address worked.

I can do that too, no problem.

The issues is, as I explained in an earlier post, that I can't reply to emails sent to my Hide My Email address from somebody else (a company).

I'm trying to reply to email from a company to whom I gave a "Hide My Email" address to.
When I click on "Reply" I get the usual new mail including the quoted original message, but the recipient's address, and my "Hide My Email" address are greyed out, but I can type my reply.

When I attempt to send I get the message in my screenshot.
 
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