Hi,

I am trying to reply by an email, but get the following error message: "The message can't be sent because at least one recipient isn't valid."

Recipient address as appears in the "TO" field is something like - ddd @ a . b . c  < ddd+  11111111-2222-AAAA-FFFFF 333333333333@ a . b . c

I have already saw a similar issue on the Internet, and it seems the reason for that is having the '+' character in the recipient address.

I am using Exchange 2013 (Windows server 2010 SP1).

Is it a known bug?

Is there any workaround?

Thanks a lot.

Avital

Hi ,

Before replying for that email just look the problematic email address on the received email is seems to be in a valid format ?

Hi,

This thread explains valid and invalid email address characters very well.

https://social.technet.microsoft.com/Forums/exchange/en-US/69f393aa-d555-4f8f-bb16-c636a129fc25/what-are-valid-and-invalid-email-address-characters

The recipient address in the "TO" field seems to have two @ character in the address?

Please check if this issue occurred on both outlook and OWA.

Does this issue affect all recipients or only this recipient?

Please enable message tracking and search message tracking log to see if there is any related message for further analysis.

Best Regards.

Hi,

This thread explains valid and invalid email address characters very well.

https://social.technet.microsoft.com/Forums/exchange/en-US/69f393aa-d555-4f8f-bb16-c636a129fc25/what-are-valid-and-invalid-email-address-characters

The recipient address in the "TO" field seems to have two @ character in the address?

Please check if this issue occurred on both outlook and OWA.

Does this issue affect all recipients or only this recipient?

Please enable message tracking and search message tracking log to see if there is any related message for further analysis.

Best Regards.

• Marked as answer by Simon_WuMicrosoft contingent staff, Moderator Tuesday, February 17, 2015 9:41 AM

Hi,

This thread explains valid and invalid email address characters very well.

https://social.technet.microsoft.com/Forums/exchange/en-US/69f393aa-d555-4f8f-bb16-c636a129fc25/what-are-valid-and-invalid-email-address-characters

The recipient address in the "TO" field seems to have two @ character in the address?

Please check if this issue occurred on both outlook and OWA.

Does this issue affect all recipients or only this recipient?

Please enable message tracking and search message tracking log to see if there is any related message for further analysis.

Best Regards.

• Marked as answer by Simon_WuMicrosoft contingent staff, Moderator Tuesday, February 17, 2015 9:41 AM

Hi,

The mail that appears when I hit the reply button is in the following format:

str@app.gy.com <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>;

When hitting the send button I get "The message can't be sent because at least one recipient isn't valid. No Match was found".
This happens when using OWA client  with Exchange 2013 and windows server 2012, but when using Exchange 2010, it didn't happen, it works fine.

Do you have a solution for that?

Thanks

Hi Avitala ,

                 If you are trying to send mail through Outlook (say version 2013) ,goto Files  -> options -> mail -> and under send message option their is a button "Empty auto complete list" to clear the cache values .Click on that button and press yes when prompted for confirmation.

       Now try to send the email to whom you want to send and i hope that, the message has been successfully delivered this time.

 If this solution solves your problem ,then the reason for this might be the change in smtp address.When you are typing the email address it might be pointing to the incorrect email address of the recipient whose mailbox might have been moved to a different mailbox server.

The second solution that you can try is to update the address book .Update the addess book from the server and also try to download the address book local to your computer .Restart your outlook and again try to send.

Hope this solves your problem.

Best Regards ,

Zohaib

Mark as answer if this solves your problem.

• Edited by Successs 23 minutes ago

Hi Zohaib,

In outlook 2013 it works fine, unfortunately the problem occurs only in OWA.

Do you have any suggestions?

Thanks,

Avitala

P.S

Just a note that I'm not typing the email address, it is generated automatically when I hit the reply button.

Hi ,

     Yes i know it gets generated automatically but  What i want you to do is to delete that email address when you hit the reply button and re-enter the same email address manually whether it is OWA or outlook.

Have you updated your address book ,if not try to update your address book as i have already told you.

Is this issue is only with specific user .

Thanks,

Zohaib

• Edited by Successs 21 hours 5 minutes ago

Hi Avitala ,

                 If you are trying to send mail through Outlook (say version 2013) ,goto Files  -> options -> mail -> and under send message option their is a button "Empty auto complete list" to clear the cache values .Click on that button and press yes when prompted for confirmation.

       Now try to send the email to whom you want to send and i hope that, the message has been successfully delivered this time.

 If this solution solves your problem ,then the reason for this might be the change in smtp address.When you are typing the email address it might be pointing to the incorrect email address of the recipient whose mailbox might have been moved to a different mailbox server.

The second solution that you can try is to update the address book .Update the addess book from the server and also try to download the address book local to your computer .Restart your outlook and again try to send.

Hope this solves your problem.

Best Regards ,

Zohaib

Mark as answer if this solves your problem.

• Edited by Successs Monday, April 06, 2015 7:02 AM

Hi,

Thanks for the quick response.

1. I delete the email address when I hit the reply button and re-enter the same email address manually as you requested. Then, it was converted automatically to the first part of the email without the angle brackets i.e str@app.gy.com <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>;  will be converted to str@app.gy.com;

Now when hitting the send button, there is no error and the email is sent to its destination. But it is not a legitimate solution to change it manually each time.

2. I did not updated the address book. Can you tell me what exactly should I update and how should I do it, since I am not familiar with it. (only in OWA, since I have devices that do not have outlook at all).

3. This issue is not with a specific user.

Thanks,

Avital

• Edited by Avitala 19 hours 27 minutes ago

Hi Avital ,

             Below are the commands to update the Offline address book and the Global address list. Try to run the command one by one and check the result  so as to narrow down the solution.You can also refer to microsoft technet site for more details on below commands.

            And since my previous reply has proved to be a solution ,so mark it as answer as it will benifit others who might face this kind of problem.  

Update-OfflineAddressBook -Identity "My OAB"

Update-GlobalAddressList -Identity "Global Address List"

Thanks,

Zohaib

Hi ,

     Yes i know it gets generated automatically but  What i want you to do is to delete that email address when you hit the reply button and re-enter the same email address manually whether it is OWA or outlook.

Have you updated your address book ,if not try to update your address book as i have already told you.

Is this issue is only with specific user .

Thanks,

Zohaib

• Edited by Successs Monday, April 06, 2015 10:19 AM

Hi Zohaib,

From what I saw, in the exchange 2013, these configurations can be done from a web-ui not from a command line as it was in exchange 2010.

I updated all the Address lists from the web-ui through organization->address lists->update.

The problem still occurs.

For others to know, if you try to run these commands and they are not recognized try to run this first:

#Enable Exchange cmdlets
add-pssnapin *exchange* -erroraction SilentlyContinueT

The details can be seen here: http://petermorrissey.blogspot.co.il/2013/01/enabling-exchange-cmdlets-in-powershell.html

Let me see if I understood you well, you wanted the address to be in the address-list ahead and that way it should be recognized, am I right?

If indeed, it does not help me since the mail is generated differently each time (the number after the "+" is different from mail to another).

The same source can send 2 different mail:

1. str@app.gy.com <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>; 

2. str@app.gy.com <str+222A4666-AWED-A6BV-22C6-1CBB7D3A3D43@app.gy.com>; 

In these two times when I reply it should be sent to the same origin with this different id. (reminder in exchange 2010 it worked fine)

Writing a long string mail manually does not seem a realistic solution to me.

Please help,

Thanks,

Avital

• Edited by Avitala 16 hours 56 minutes ago

Hi,

Thanks for the quick response.

1. I delete the email address when I hit the reply button and re-enter the same email address manually as you requested. Then, it was converted automatically to the first part of the email without the angle brackets i.e str@app.gy.com <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>;  will be converted to str@app.gy.com;

Now when hitting the send button, there is no error and the email is sent to its destination. But it is not a legitimate solution to change it manually each time.

2. I did not updated the address book. Can you tell me what exactly should I update and how should I do it, since I am not familiar with it. (only in OWA, since I have devices that do not have outlook at all).

3. This issue is not with a specific user.

Thanks,

Avital

• Edited by Avitala Monday, April 06, 2015 11:57 AM

Hi Zohaib,

From what I saw, in the exchange 2013, these configurations can be done from a web-ui not from a command line as it was in exchange 2010.

I updated all the Address lists from the web-ui through organization->address lists->update.

The problem still occurs.

For others to know, if you try to run these commands and they are not recognized try to run this first:

#Enable Exchange cmdlets
add-pssnapin *exchange* -erroraction SilentlyContinueT

The details can be seen here: http://petermorrissey.blogspot.co.il/2013/01/enabling-exchange-cmdlets-in-powershell.html

Let me see if I understood you well, you wanted the address to be in the address-list ahead and that way it should be recognized, am I right?

If indeed, it does not help me since the mail is generated differently each time (the number after the "+" is different from mail to another).

The same source can send 2 different mail:

1. str@app.gy.com <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>; 

2. str@app.gy.com <str+222A4666-AWED-A6BV-22C6-1CBB7D3A3D43@app.gy.com>; 

In these two times when I reply it should be sent to the same origin with this different id. (reminder in exchange 2010 it worked fine)

Writing a long string mail manually does not seem a realistic solution to me.

Please help,

Thanks,

Avital

• Edited by Avitala Monday, April 06, 2015 2:27 PM

Hi Avital ,

             Deleting the cache has to be done only once for all the cached email address and this has to be done for all the OWA users.

      What is happening when you are clicking on the reply button after you have deleted the cached email address. Are you getting that long string email address or the correct email address format. 

Thanks,

Zohaib.

Hi Zohaib,

I've tried to delete the cache email address so there will be no auto complete for emails.

Moreover, I tried to reply a new email (meaning an email that was never in my list before).

In both cases, when clicking on the reply button I get the long string email which is the correct one including the "+" character in it.

This is the same as before. (before deleting cache).

When clicking the send button I get the same error:

"The message can't be sent because at least one recipient isn't valid." 

To be clear:

I want to send an email to someone, and add an identifier to the Reply-To header.

So the from header  will be: str@app.gy.com

and the Reply-To header will be: "str@app.gy.com" <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>;

and when clicking the reply button the to should be "str@app.gy.com" <str+123A4567-ABCD-A7BC-12A3-1ABC2D3A4D56@app.gy.com>; 

as it is today but it does not let to send this mail.

Do you have any suggestions how to solve this error?

Thanks,

Shai

• Edited by Avitala 16 hours 46 minutes ago