How to send from an email address alias?

Most people have multiple aliases on their mailbox, with aliases on the same email domain or even with multiple domain names. But when you try to send from (send as) one of these aliases you get the following undeliverable error message returned:

“You can’t send a message on behalf of this user unless you have permission to do so. Please make sure you’re sending on behalf of the correct sender, or request the necessary permission. If the problem continues, please contact your helpdesk.”

The answer to this problem is relatively easy, by default and design this isn’t possible, but there are a couple of workarounds available:

  • Create a separate mailbox and put the alias on the mailbox and configure it with send as permissions.
  • Create a distribution group and put the alias on the distribution group and configure it with send as permissions.
  • Create a dummy pop account in outlook and configure the alias as email address.
  • There are some third party tools available that create a workaround.



Workaround 1:
Create a separate mailbox and put the alias on the mailbox and configure it with send as permissions.

First we start with removing the alias we want to send as from the original mailbox.

Now we create a new mailbox, give it a logical name, etc. and give the alias as email address.

After the account has been created we need to set Send As permissions for the newly created account. We do this via the Exchange management console by right clicking on the newly created mailbox and choose Manage Send As permissions…

Add the original user (user@domain.com) to grant Send As permission for the alias@seconddomain.com

Now you are able to send as user@domain.com also with the alias@seconddomain.com address.

We do this by using the From… field in outlook, add the alias in the from field when you want to send from the alias. When you don’t see the from field go to the options menu and choose Show From.

Best thing to do is click the From… button and select the alias mailbox from the address list.

Of course when email is send to the alias@seconddomain.com it now will be delivered to this newly created mailbox. If you would like to receive the email just as before in the same mailbox (user@domain.com), then go to the properties of the newly created alias mailbox and choose the Mail Flow Settings tab, select Delivery Options… and choose properties.

Add the original mailbox at the Forward to: field, via the Browse… button. Now all mail is forwarded to your original mailbox and all mail will be in same mailbox as before removing the alias.




Workaround 2:
Create a distribution group and put the alias on the distribution group and configure it with send as permissions.

First we start with removing the alias we want to send as from the original mailbox.

Now we create a new distribution group, give it a logical name, I always give it the name of the email alias and set the alias as email address.

Then we add the original mailbox as only member.

Now we need to set the Send As permissions for the original mailbox (user@domain.com) on the newly created distribution list. This cannot be done via the exchange management console, we have to use the exchange management shell.

This is the command syntax: Add-ADPermission “public folder name ” -ExtendedRights Send-As -user “Domain\Username”

Now you are able to send as user@domain.com also with the alias@seconddomain.com address.

We do this by using the From… field in outlook, add the alias in the from field when you want to send from the alias. When you don’t see the from field go to the options menu and choose Show From.

Best thing to do is click the From… button and select the alias distribution group from the address list.




Workaround 3:
Create a dummy pop account in outlook and configure the alias as email address.

WARNING: This option is the least recommended, because setting up this will create the posibillity to open a security hole for smtp virusses.

With this workaround we leave the email aliases as they are on the mailbox. We are going to configure a dummy / fake pop account in outlook, so no server configuration needed.
Open outlook and go to Account Settings, choose for New…, choose the email services that include Pop3, choose for manual configure server settings and choose Internet E-mail (Pop).

At Your Name: we give your name (this is the name the receiver will see), at E-mail Address we give alias@seconddomain.com, at incoming mail server, just give in something it doesn’t matter, at outgoing mail server give in your Exchange server and at username and password give in your logon credentials (the users domain account credentials).

Choose More Settings…

Make sure that you enable “My outgoing server (SMTP) requires authentication” on the Outgoing Server tab. This is needed to let you send via your exchange server, then finish the wizard.

Now you are able to send as user@domain.com also with the alias@seconddomain.com address.

We do this by using the Account button that is created after creating the dummy pop account. You just choose the email address you would like to send your email from.



Conclusion:
So you see there are a couple of workarounds available, which one is the best, there isn’t it all depends on your needs and wishes.



41 Responses to “How to send from an email address alias?”

  1. David says:

    Hi there,

    I am not dealing with this exact sily problem.. Who would have thought that such an advanced system would have such a basic problem..

    Quick question – is there a way to default it so that Outlook will use the relevant email address when replying to an email? so if someone emails me to my alias mail address then when replying to that email I won’t have to manually select the alias sending address. Outlook should see that the original email was sent to the alias and should choose the alias email address when replying.

    Makes sense?

    Thanks!

  2. David says:

    Silly correction..

    I am *now* dealing with…….

  3. Starr says:

    I’m reading through this and think it might address my issue but I’m not sure. I have 3 POP domains for 3 different businesses I run. I want to add an exchange account with a neutral domain (e.g. me@lastnamemail.com) and have the other 3 pop accounts forward to it so it’s all in one box – the reason for wanting exchange is so when I address a message on my phone i don’t have to go back to my desktop and see it still there, and visa-versa. The issue I am trying to work around is granting permissions to reply “from” the pop accounts’ address. Ultimately I can live with replies from the generic address, but I’d like to have them be from or even on behalf of the respective biz address. If I understand correctly, setting them up as separate accounts in outlook won’t resolve the phone vs desktop issue which is the whole reason I want exchange (and it’s not affordable to upgrade all of the other addresses to exchange). Thanks.

    • ronnypot says:

      Just to be sure, you want to send as or on behalf of the pop account via your mobile phone, or just via outlook. If it is via outlook you can use the described method, this won’t work via your phone, or you need to create separate accounts on your phone as well, if this is supported. Than you should be able to send with these address from your phone. You might need to look if this it is possible, to create multiple exchange accounts with your mobile phone.

  4. R. says:

    Does this work for SBS 2011 also?

  5. R. says:

    I see what I was doing wrong. I didn’t create a second domain for the email alias…

    Is it possible to add the domain name hotmail.com, gmail.com, or any other existing one where I do not have access to the MX records as long as the POP3 Connector is used for downloading the mail to the server?

  6. R. says:

    Do to other things, I was never able to get back around to making an alias. I finally have some time to revisit this and I thought I would start from the beginning – clean install on test server…

    Do I have to create another user account for the alias?

    When trying to follow Workaround 1, I am not able to get past this step: give the alias as email address.

    When I try to put the alias as testing@seconddomain.com, I get an error saying something about how the @ is not allowed.

    • ronnypot says:

      Yes within workarround 1 you create another user account for the alias.

      The email address must be entered within the email addresses tab, it might go wrong if you enter the complete email address within the alias field.

      If this is not what you mean can you please send me or post a screen capture of the error you get?

  7. R. says:

    In the 3rd picture, you have “alias@seconddomain.com Properties” meaning that the user name is “alias@seconddomain.com” (at least the alias for the user name).

    How were you able to do that?

  8. R. says:

    I have a head scratcher now…

    When I send an email to my hotmail account, the return alias is the same as the alias on the hotmail account.

    This is what it is sent as:

    From SBS account: Test Alias
    To Hotmail account: Hotmail Alias

    This is what the return address shows up as:

    Hotmail Alias ( not Test Alias )

  9. R. says:

    From SBS account: Test Alias (user@seconddomain.com)
    To Hotmail account: Hotmail Alias (user@hotmail.com)

    This is what the return address shows up as:

    Hotmail Alias (user@seconddomain.com) and not Test Alias (user@seconddomain.com)

  10. Victor says:

    There exists a useful tool to send as you like: http://www.ivasoft.com/choosefrom2007.shtml

  11. Catherine says:

    Ok. I’ve deleted the alias from original mailbox. However, when I try to create new mailbox with the alias, it says it’s already in use by original user. How long does it take for Exchange to realize the email address is available?

    Thanks.

    • ronnypot says:

      If you deleted the alias it should be recognized direct by exchange. It might be you have an email address policy that automaticaly put the alias back to the original mailbox?

  12. molski says:

    Hi,

    Today I tried workaround 2. Deleting the alias from the user goes okay, creating the Distribution Group goes okay. Adding the user and emailaddress of the second domain to the Distribution Group goes okay, even completing the CLI command goes fine (although I don’t see the “Creating …” line after submitting the command, but when I repeat it, it says that things already are appli3d to that Distribution Group). But I still get the same error :( I’m using Exch 2010 SP2 on Win2K8 R2.

    Any ideas what I’m doing wrong?

    Regards,
    Molski

    • ronnypot says:

      Hi,

      Don’t know if you already figured this out, but to be sure, the alias is now added to the distribution list? But when you try to send as you still get the error?

  13. Sam J says:

    Great post – well written and screenshot.

    I’ve just being doing some of this in SBS2011 and found that in Exchange Shell I had to use:

    Add-ADPermission “the dist-list alias” -ExtendedRights Send-As -user “the user alias”

    instead of:

    Add-ADPermission “public folder name ” -ExtendedRights Send-As -user “Domain\Username”

    Otherwise – brilliant. Thanks

  14. Tocom says:

    We have choosen Workaround 2 and we also want to receive email from alias distrubution list forwarded to users mailbox. Second domain is set in Accepted domain and users have been able to reveive email earlier before i implented this Workaround 2. Now users can not receive email sender receive this error when they send mail to second domain.

    administrator@seconddomain.no den 04.09.2012 09:44
    You do not have permission to send to this recipient. For assistance, contact your system administrator.

    What can we do?

  15. Tocom says:

    Everything is working now.

  16. James Hurrell says:

    Thanks Ronny – I have this exact situation on SBS 2011: client has two domains and cannot decide which one they want to use. Some users are set to domain A and some to domain B with Email Policies. But now they want to Send As as well.

    I used WA 2 and it is perfect. Just a few things to mention:

    For those that have policies in place: you need to untick the “Automatically update email addresses based on e-mail address policy” option in the “Email addresses” tab of the Distribution Group otherwise you’ll hit an error when you try to apply the changes to the group.

    I also created the Dist. Groups directly in EMC, not in the SBS console – as such the groups don’t appear in SBS Console – not really an issue. Note though that doing and leaving the box to choose the Organizational Unit will put the Dist Group in the MyBusiness/Users/SBS Users unit – I choose to put them in MyBusiness/Distribution Groups.

    But great instructions Ronny, thank you.

  17. wim says:

    Goodmorning,
    Does workaround 1 also work when there is no second authoritive domain in Exchange for ‘Alias@seconddomain.com’ and the mail is imported into exchange by using a pop connector (where ‘seconddomain.com’ will be added to the pop connector delivering the mail to the second mailbox)?
    Kind regards, Wim

    • ronnypot says:

      Hi Wim,
      I have never tried if it might work when the domain is not configured as an authoritive domain. I think it would not work because this is more or the less relaying what you are trying to do.

  18. James Hurrell says:

    Ronny – I wanted to make it known that there is a nasty side effect of not using the SBS wizard to create the Distribution Group for Work Around 2. As I reported yesterday, I did not do this and instead used EMC. The setup was fine, and the user could Send As that alias no problem. However, Exchange would reply with User Unknown when sending to that alias.

    I then deleted the Dist Group and recreated it using the SBS wizard, and then adapted it as per your instructions. This time mail was received fine on the alias.

    So the old adage for SBS to “use the wizards”, “use the wizards”, “use the wizards” still holds true even for this!

    Hope this might be of use – I had the user in question complaining that they had received no email…. Luckily the front end ExchnageDefender had a copy of the mail that bounced, so all was not lost.

  19. i cant send email from alias says:

    Dear Sir,

    please help me how to send an email from alias account. Kindly send me step by step process

    • ronnypot says:

      Did you read the article, because it says you can’t and there are tree work arrounds to solve this problem all described here.

  20. Rene says:

    Hi Randy,

    I have the exchange 2003 than i’m adding the exchange 2010 now and i’m at the state that all my mailboxes are not move to the Ex2010.
    I’m trying to do the W2 but i’m not sure. Didi it stat at the line W2 or before ?

    Best regards

  21. Rene says:

    Hi,

    Last line was: Did it start at the line W2 or before ?
    And is that better to do on the exchange 2010 or 2003 and move after ?

    • ronnypot says:

      Hi,

      If you are not using it now I would recommend to do it after the migration and the W2 starts at the line from W2 down

  22. Great article, just what I’m looking for, except I’m trying workaround #1, but the problem is when I delete the email and hit apply, the email just pops back up after apply has been hit. It won’t let me delete the email.

    Let’s say the account is structured like this.
    bob@domain1.com
    bob@domain2.com
    bob@domain3.com

    Delete 2 – no problem. then hit apply and it’s back. Does that make any sense?

  23. to answer my previous question. It turns out I have to uncheck the “Automatically update e-mail addresses based on e-mail address policy” box.

Leave a Reply

Current day month ye@r *

Sharing Buttons by Linksku