ChooseFrom for Exchange 2013/2016/2019


Exchange mailbox may have multiple SMTP addresses. For outgoing messages Exchange server always uses the primary SMTP address. For example, John Doe has a mailbox with [email protected] primary SMTP address and [email protected] secondary smtp address. John Doe can easily receive the message addressed both to [email protected] and [email protected], but he can not send the message as [email protected] because this behaviour is by design in Exchange server.
ChooseFrom for Microsoft® Exchange 2013/2016/2019 application allows users to send a message with any of their own SMTP addresses as the From address.
The application is a custom transport agent.

Current version:


  • You do not need to create an additional “fake” mailbox or contact specifically for storing an additional From address
  • The application is server-centric, so you do not need to install any extra software on the client side
  • ChooseFrom can work both for on-line and on-site users if you have a hybrid configuration (an Exchange server hybrid deployment)


On your Exchange 2013/2016/2019 Mailbox server computer:

  1. Select (or create) a user account that is a member of the local Administrators and Domain Users security group.
  2. Log on as that user.
  3. Create C:\Program Files\IvaSoft\ChooseFrom\ directory and download there archive file.
  4. Right-click and select ‘Properties’. If there is ‘Unblock’ button, hit it.
  5. Extract all files from the zip archive to C:\Program Files\IvaSoft\ChooseFrom directory.
  6. Run ChooseFrom2013Setup.exe. Click Install button. Make sure that ChooseFrom2013 is appeared in the list of Transport agents. Click Enable button. Click Exit button to close the program.


  1. Make sure your mailbox has more than one SMTP address. Ask your Exchange admin to add the following additional SMTP address:
    john.doe[email protected]
    to your mailbox.
  2. Open Outlook and create a new mail message. Click View->Options and fill “Have replies sent to:” field with
    Click Close button.
  3. Send your message to any external Internet address you can operate.
  4. Receive the message you have just sent using any SMTP/POP3 e-mail client (for example, Outlook Express).
  5. Make sure the sender address (the From: field) is [email protected]

We have tested ChooseFrom on Exchange 2013 CU20, on Exchange 2016 CU10 and on Exchange 2019 CU1 server.
In all cases it was a single server that plays Client Access and Mailbox roles.

If you are planning to use the Mac, iOS (iPhone etc) or Android-based devices, you should check “Inspect the Subject line for ‘Sendas:[email protected]’ tag” box. Now, to send from a non-default address, you have to modify the subject line.


By default users can send as their own SMTP addresses only.
However, it is possible to bypass this limitation by creating a security group named SENDASANYONE and placing there the user accounts you wish to be able to send as anyone.

Side Effects

The main side effect is that you can not exploit Outlook “Have replies sent to:” field as usual. If an outgoing message has the reply-to address filled out, ChooseFrom will set this address as the From: field and the Reply-to: field will be removed completely.

Client-side application that can cooperate with ChooseFrom

There exists an Outlook utility named SmartReply that allows an Outlook user the ability to easily select the From address of the new, replied or forwarded message. SmartReply 2010 is compatible with Outlook 2010/2013/2016/2019.

Server-side applications that are compatible with ChooseFrom

  • CodeTwo Exchange Rules Pro ver.2.X. How to set up rules: an example.
  • Exclaimer Mail Disclaimers


Run ChooseFrom2013Setup.exe. Click Uninstall button. Make sure that ChooseFrom2013 is not in the list of Transport agents. Click Exit button to close the program.

About this demo version.

ChooseFrom demo version adds “[ChooseFrom2013 DEMO]” to the Subject line of each message processed.


Q. I am having trouble getting the program to work. When I enable the transport agent, I get 1052 and 16023 errors in Event Viewer and the Transport service will not stay running.
A. Make sure that you have placed the software files to C:\Program Files\IvaSoft\ChooseFrom folder. Also note that Exchange server uses the Network Service account for the Transport Service credentials and it seems this account didn’t get security permissions to ChooseFrom folder. Try to add Network Service account read permissions to that folder.

Q. I am about to purchase this product but I wondering regarding updates/patches. What are the policies regarding updates? Do you provide them freely or as a purchase?
A. As a registered user, you will get free updates for one year from the date of purchase.
Once the new version is ready, this information will be e-mailed to all registered users. We will send updates via e-mail to those who request them.

Q.  I have already ordered your software and want to view data relating to my order.
A.  Just visit our Customer Care Center.

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