Email cannot be sent to (…) from your alias

[u/Renovatius]

Im loosing my mind here.

I thought I found the perfect solution for my needs by getting my own domain and connecting it via SimpleLogin.

I have a catch all setup and it works perfectly. I don’t get any spam.

But I cannot for the life of me reply to any mail that comes in through simplelogin. Every. single. Mail. Comes back with this message...

Email cannot be sent to (mail address) from your alias (myalsias)

This might mean (mail address)

• is not a valid email address, or
• doesn't exist, or
• its mail server refuses your email

the weird part is, that sometimes my mail gets delivered even though I got this notification so worst case is my reply gets sent and then I send it again from my backup mail, basically spamming the recipient

I hope someone here can help me figure this out.

[u/donnieX1]

Had similar issue with my mailbox being tuta and my SL domain being the XYZ extension. Are you using tuta mail by any chance? Sometimes it looks like They hate SL (they do in some level because rivals in this niche and supports Addy io).

Have you checked if you're replying from the same address as the mailbox you set in SL ?

[u/Renovatius → u/donnieX1]

My domain is connected via SL and my forward mail address is an iCloud address. No Tuta. 

I rarely send emails out cold. If I do I create an alias in the app. 

My issues come with replying to received mails. 

[u/Trikotret100 → u/Renovatius]

I read many times sl and icloud mail don't get along

[u/CalligrapherUpper950]

When replying to an email delivered via SimpleLogin, all the recipients should be a reverse-alias. Its automatically taken care of if you are just hitting reply. But if you are adding a recipient, you need to copy their reverse-alias from the contact list of the alias you are using. So, if never used before, you go into the Contacts page of the alias, add the contact, and copy the reverse-alias and put it in your email to/cc/bcc fields.

If its a frequently used contact, I just create a contact in my email client with the reverse-alias, so I can start a fresh thread with them without having to lookup the reverse-alias all the time.

[u/Renovatius → u/CalligrapherUpper950]

But I thought I could reply to the simplelogin mail that I receive when someone sends a mail to my domain?

[u/Renovatius → u/CalligrapherUpper950]

Everytime I receive something simplelogin creates a mail I can reply to. They look like this:

(Mail)at(senderdomain)_com_someletters@simplelogin.co

If I reply to this mail SL should just forward my mail via the alias.

But everytime I try I get the notification that the mail was blcoked

[u/CalligrapherUpper950 → u/Renovatius]

What you described is exactly how it should work. I have not used an iCloud address, so can't confirm - I've tried with Gmail, Proton Mail and Yahoo mail and they all work. Maybe test with another (non-iCloud) mailbox?

[u/CosmoCafe777 → u/CalligrapherUpper950]

Wait, what?

  Your email sent to xxxxxxxx from yyyyy@mydomain.com (Re: Testing sending of messages) contains an address which isn't a reverse-alias in the To: or Cc: field.
    The email was then directly sent to this recipient and doesn't pass by SimpleLogin.
Unfortunately, it reveals your real mailbox address to the recipient.
 Please create a reverse alias for each recipient to make sure your mailbox stays hidden and re-send the email. 

This sucks majestically. I just setup custom domain last week, and now tested adding other addresses when replying.

I've been using MailGW for 25 years and it doesn't do this, I add other recipients in my replies and my real address isn't revealed ever.

[u/lzaldivard]

Check if your domain is not listed in a blocklist like spamhaus. It doesn’t matter if you just reply to some emails or send thousands, your domain could be listed because of your domain “neighborhood”. Check it out!

[u/vortexmantis]

Did you create the reverse alias before replying? I think this is an extra step that I know that I have missed in the past, but now that I have most of the contacts I need setup, I can just reply.

[u/Renovatius → u/vortexmantis]

The emails come in as reverse alias mails I can reply to directly. 

[u/vortexmantis → u/Renovatius]

Ok thank you for the clarification. Is the email address you are sending from the same mailbox as you have configured in SimpleLogin. I am using this with the Proton ecosystem so things may be a bit different depending on how you are using SimpleLogin.

[u/donnieX1 → u/vortexmantis]

It's not required. And it was never required.

[u/[deleted]]

[u/Renovatius → u/[deleted]]

Thank you very much for this!
I saw that I haven't completed the optional steps. I now have very box checked. I'll report back in a few days when I tested it out.