Sending E-Mail from Multiple Defined E-mail addresses.

Currently we are using exchange 2013. Let's say a user has a mailbox account for John Doe and assign a default e-mail address of [email protected] Now I go ahead and define additional e-mail addresses of [email protected] and [email protected]
now John would like to start sending and receiving e-mails using all 3 defined e-mail addresses. How does one set this up. It seen that outlook 2013 only allows "on behalf of" sending and exchange only allows you to send e-mail using your default
e-mail address?
Best Regards
Best Regards

See the Exchange section in:
http://www.howto-outlook.com/faq/aliases.htm
and also:
Sending from an additional Exchange address
Robert Sparnaaij
[MVP-Outlook]
Outlook guides and more: HowTo-Outlook.com
Outlook Quick Tips: MSOutlook.info

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    Set objConfig = CreateObject("CDO.Configuration")     
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         .Item("http://schemas.microsoft.com/cdo/configuration/sendusing") = intSendUsing
         .Item("http://schemas.microsoft.com/cdo/configuration/smtpserver") = strSMTPServer
         .Item("http://schemas.microsoft.com/cdo/configuration/smtpserverport")= intSMTPPort
         .Item("http://schemas.microsoft.com/cdo/configuration/smtpconnectiontimeout") = 10
         .Update
    End With
    'Create CDO message object
    Set objMsg = CreateObject("CDO.Message")     
    'Assign config object to configuration property of message object
    Set objMsg.Configuration = objConfig
    'Set Message object settings and send mail
    With objMsg
         .To = strToAddress
         .From = strFromAddress
         .Subject = strSubject
         .TextBody = strEmailMsgLine
         .Send
    End With
    'Destroy message objects
    Set objMsg = Nothing
    Set objConfig = Nothing
    When I set 'CdoSendUsing' to 1, an eml file gets generated on the path 'C:\Inetpub\mailroot\Pickup' but I never receive it on my gmail ID. When I set the 'CdoSendUsing' to 2, I get an error on the .Send line saying 'The server rejected the sender address. Server response was 530 5.7.0 must issue a STARTTLS command first'. I also checked the MetaBase.XML, 'PickupDirectory' is set.
    Please suggest where am I going wrong.
    Thanks & Regards!

    Just to confirm what Tony is saying :
    - It's highly unlikely that Google functions as a Mail Relay for SMTP. If it did spammers would have a field day. An open relay is a mail server that will forward emails sent to it from unknown 3rd parties. I'm not familiar with your Google service; however, if they allow any type of mail relaying form you, it is probably secure with at least a login and password so they know it is coming from you. (This would mean when you use the CDONTS object, you'll need to supply a sender login and password)
    - The reason why files are accumulating in the Pickup folder is you do not have a running SMTP service that is processing emails on the server that you pointed FDM to. For reference, the following folders are used by your typical SMTP mail service :
    * Pickup : Email files waiting to be picked up by the SMTP server for processing (if you open the EML file in a text editor, should be apparent what it is) If the email is meant for an external party, it will be sent to their mail server. If the message is meant for an internal user, gets moved to Drop folder.
    * Drop : Incoming messages for local users are stored here
    * Queue : Messages that were sent but could not be immediately delivered are placed here. These will be resent at various intervals for a predetermined amount of attempts.
    * Badmail : Messages that could not be delivered. Viewing in a text editor should indicate the failure, etc. Senders are not notified of these failures in most cases unless an Admin notifies them based on what is in this folder.
    The easiest option here is to install SMTP on the FDM box and call it a day.
    * MS Install Instructions for Server 2003 - http://www.microsoft.com/technet/prodtechnol/WindowsServer2003/Library/IIS/e4cf06f5-9a36-474b-ba78-3f287a2b88f2.mspx?mfr=true
    * MS Configuration information for SMTP on IIS 6.0
    http://www.microsoft.com/technet/prodtechnol/WindowsServer2003/Library/IIS/e4cf06f5-9a36-474b-ba78-3f287a2b88f2.mspx?mfr=true
    One NOTE :
    - If your company has a mailserver (who doesn't?? :) ), the MX record will be linked to the IP of that machine and not your SMTP box. Certain anti-spam solutions as well as other mail servers might reject your emails as when they perform a reverse lookup, the IP address of your SMTP server will not match that of your MX entry (DNS).
    If this happens, you should configure your FDM SMTP server to send its mail to your local mail server and talk to your IT department to make sure all necessary changes are in place. (i.e. you might need to configure Exchange to let your FDM SMTP use it as a mail relay, etc)

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