Hide my EMail when replying - WTF?

[spot4u]

I just used hid my EMail to contact a Company an complaing about something. The Company responded using ZenDesk and the EMail got delivered to me.
I wanted to reply on Mac Mail (Sequioa 15.5) and hit the reply button. I could not change the Mail header i.e. change the Recepient or add CC: or BCC: and as Sender I could see my HME address...

However after the mail was sent, I noticed that Mail has sent it with my regular EMail address over my google account. Even though as sender was clearly the HME address set and the field was greyed out - unchangeable.

WTF?

 

[BigBlur]

That's how it works. Hide My Email is a relay service...you don't actually send from your hidden email address. You need to check who you sent it to. It should be an @icloud.com address, which then Apple strips out your info and relays it on to the intended recipient. The recipient replies to your hidden address (also an @icloud.com address), which Apple then relays back to your actual address.

I've got a post explaining it in more detail here.

 

[spot4u]

But that is not what it suggests... When I send a Mail I can choose my sender EMail. It also offers a HME Sender EMail. What use would that be if it then sends it via the primary Address?

 

[svenmany]

I just used hid my EMail to contact a Company an complaing about something. The Company responded using ZenDesk and the EMail got delivered to me.
I wanted to reply on Mac Mail (Sequioa 15.5) and hit the reply button. I could not change the Mail header i.e. change the Recepient or add CC: or BCC: and as Sender I could see my HME address...

However after the mail was sent, I noticed that Mail has sent it with my regular EMail address over my google account. Even though as sender was clearly the HME address set and the field was greyed out - unchangeable.

WTF?

That is strange. My replies from the iCloud account used the iCloud smtp server. Perhaps you have something set incorrectly. When I select my iCloud account in Settings, I see that the "Outgoing Mail Account" is set to iCloud. I really don't know what would happen if I were to change that to one of the many other SMTP servers I've configured. Certainly google's SMTP server would not accept mail from a masked email address unless you went through a registration process for that specific email.

When I ran a test sending back and forth from my iCloud account to an account I have on another mail server it worked fine. The mail in the sent mail folder showed my real address, but the mail received on the other account did not. (I looked at the source of both emails.) That is consistent with the intuition that the iCloud SMTP server is altering the email headers.

 

[spot4u]

This is how the reply to window looked like, it was safe to assume it would use HME instead of the GMail account. Note the greyed out From: and To: fields. Only the Subject field can be edited.

 

[svenmany]

What does it show in settings? Does the outgoing mail account show as iCloud?

 

[svenmany]

I am not able to generate a new HME address if the outgoing mail account is not iCloud. However, I am able to respond with an HME address with the outgoing mail account set to gmail. The email sent shows up in my sent mail on gmail, exposing my email address. But the recipient's email address was rewritten (like finalRecipient_encodingOfMyHMEAddress@icloud.com) so that google's SMTP server would relay it through iCloud. Unfortunately, the iCloud SMTP server rejected it.

So the Apple Mail program knows how to deal with this situation (using gmail smtp to send HME emails), but Apple's SMTP servers are not up to speed to support the approach.

I really don't know how your HME emails are making their way onto Google's servers and still being sent successfully to the final recipient.

 

[BigBlur]

But that is not what it suggests... When I send a Mail I can choose my sender EMail. It also offers a HME Sender EMail. What use would that be if it then sends it via the primary Address?


View attachment 2512862

I don't know how to explain it any simpler than my two posts. So far, you haven't shown or proven that it didn't work. It is expected to see your real address as the "From" address on the email in your Gmail's sent folder.

Go view the email that was sent and look at the "To" address. Is it their actual address (e.g. contactus@company.com)? If so, then something went wrong and it didn't work. Or is it some icloud.com address that looks something like contactus_at_company_com_29dk9s4o82n4o@icloud.com? If so, then it worked and your address was hidden. It would have gone to Apple, they strip out your info, and then relay/forward it on to contactus@company.com.

If you have another email address, test it out by sending yourself an email using HME (or test it with a friend/family member). Look at all the "To" and "From" addresses on your sent and received emails. Hopefully you'll get a better understanding of how the HME relay works.

 

[BigBlur]

I really don't know how your HME emails are making their way onto Google's servers and still being sent successfully to the final recipient.

You can use HME with any email account/provider you have set up in Mail; it does not require an iCloud email account. I use it with my Outlook account in Mail; spot4u happens to be using it with Gmail in Mail. You are never sending the email directly from your hidden address; that is always done on Apple's end through the relay.

When you use HME, it works something like this:

You: Hey Apple, I want to email contactus@company.com and hide my email address.
Apple: Okay, we'll have the Mail app send the email to contactus_at_company_com_29dk9s4o82n4o@icloud.com. Once we get the email, we'll strip out your info and relay it to contactus@company.com using your hidden email address, ruffle_zappy_3s@icloud.com.

You: Email is sent and shows as being sent to contactus_at_company_com_29dk9s4o82n4o@icloud.com from your real address in your email provider's Sent folder.
Apple: Receives the email, does its magic and relays it to contactus@company.com from ruffle_zappy_3s@icloud.com.

Recipient: Received email is shown as being sent from ruffle_zappy_3s@icloud.com. Recipient replies to that email address.
Apple: Receives the email and relays it back to your real address.

You: Received email is shown as being sent from contactus_at_company_com_29dk9s4o82n4o@icloud.com.


Fun fact: At this point, you don't even need to continue using the Mail app to keep your address hidden. You can now reply to that email from Outlook.com, Gmail.com, or whatever app. Your email address will remain hidden as long as you're replying to the relay address (contactus_at_company_com_29dk9s4o82n4o@icloud.com).

 

[svenmany]

You can use HME with any email account/provider you have set up in Mail; it does not require an iCloud email account. I use it with my Outlook account in Mail; spot4u happens to be using it with Gmail in Mail. You are never sending your email directly from your hidden address; that is always done on Apple's end through the relay.

When you use HME, it works something like this:

You: Hey Apple, I want to email contactus@company.com and hide my email address.
Apple: Okay, send the email to contactus_at_company_com_29dk9s4o82n4o@icloud.com. We'll strip out your info and relay it to contactus@company.com using your hidden email address, ruffle_zappy_3s@icloud.com. (The Mail app sets this up behind the scenes.)

You: Email is sent to contactus_at_company_com_29dk9s4o82n4o@icloud.com from your real address using your email provider. (Again, this is done behind the scenes.)
Apple: Receives the email, does its magic and relays it to contactus@company.com from ruffle_zappy_3s@icloud.com.

Recipient: Email appears to be from ruffle_zappy_3s@icloud.com. Recipient replies to that email address.
Apple: Receives the email and relays it back to your real address.

You: Received mail appears to be from contactus_at_company_com_29dk9s4o82n4o@icloud.com.


Fun fact: At this point, you don't even need to continue using the Mail app to keep your address hidden. You can now reply to that email from Outlook.com, Gmail.com, or whatever app. As long as you're replying to the relay address (contactus_at_company_com_29dk9s4o82n4o@icloud.com), your email will be relayed and your email address will be hidden.

Thanks for that great info.

I tested again and everything worked as you describe. Perhaps I just encountered a transient error in first test or there is some subtly that prevents it from working if you switch your SMTP server. I might play with it some, but that's a funny use case and probably of no interest to anyone else.

Maybe, as you suggest, the OP believes their address is exposed to the final recipient because they see it in their Google sent folder that way.

 

[spot4u]

Now I get it... Thanks!

The Mail is not sent to the TO: but relayed over Apples Server acting as an anonymizer in between.

Still it is somewhat confusing, when I look at the SENT Mail Foldern in Mail it will show my GMAIL Address as sender and the TO as Text, only when I inspect the TO: it reveals that in reality it was sent to Apple instead.

So everything OK maybe there could be some improvement in the UI to clearly reflect that the Mail indeed was sent over HME.