SmartReply for Microsoft Outlook

SmartReply 2010 is an utility for Exchange Server/Office 365 users who need to send mail from different addresses.

This utility allows an Outlook user the ability to easily select the From address of the new, replied or forwarded message.
The message can be replied with the same From address as original message has been sent to.
Also you can set a different signature for each e-mail address.

Current version:

SmartReply 2010 can be used solely or in cooperation with ChooseFrom for Exchange 2013/2016/2019 or ChooseFrom 365 service.

Being used solely, SmartReply 2010 can only change the Reply-To: address but not the From: address.
In combination with ChooseFrom it can change the From: address.

The utility is an Outlook COM add-in.

Typical scenarios of usage

  • Scenario 1.
    Your company has several company names that it goes under for various aspects of the business. As a result of that, you are running into the need to be able to choose which email address to send from. As the company runs Exchange, IvaSoft ChooseFrom utility has been bought and installed on the server. So far so good, but users complain about the need to fill out the “Have replies sent to:” field every time they need to send as non-default address.
    SmartReply 2010 simplifies the process of selection the From address.
  • Scenario 2.
    You are in an Exchange Server environment and have permission to send on behalf of/send as another user. You can enable the From: field from the view menu of your Outlook and select the appropriate name/address to e-mail from. However you can’t assign different signatures to different e-mail addresses then.
    SmartReply 2010 can help you to solve this problem. You do not need to install any server-side software like ChooseFrom to implement this functionality.
  • Scenario 3.
    A quote from
    Hi guys, have set up a few email addresses as aliases on a second domain for a customer (each domain dealing with a different aspect of the business).The issue is that emails sent to aliases always land in the same inbox – is there a way to have some kind of flag so the customer knows which address it has been sent to so they can reply from the correct email address and with their correct signature?

    SmartReply tool will help you to identify the address easily – just add the “E-mail account” column in Outlook as shown here.


  1. (Optional) On your Exchange server install ChooseFrom application and test it.
  2. Download archive file to any folder on your workstation. If your Outlook is 32-bit, run SmartReply2010_per-user32(DEMO).msi, otherwise SmartReply2010_per-user64(DEMO).msi. Execute appropriate msi file and follow the instructions.
  3. Run Outlook. Select File > Options > Add-ins and make sure that SmartReply2010 exists in “Active Application Add-ins” list (1). Now click “Add-in Options” button (2). Add-in Options window will appear.
  4. Select SmartReply tab. You will see your default identity that has your default (primary) SMTP address in Identities list.
    Click “Active Directory Addresses” button. Identities list will be populated with identities that matches your non-default SMTP addresses.
    Click “Shared Mbx” button. Identities list will be populated with addresses of your additional mailboxes.

    If you do not run ChooseFrom utility on the Exchange server, select <a[email protected]> radio button in “Address format:” frame.
    If you have an Exchange server in your organization make sure that Exchange Type: Onsite radio-button is selected in the Mode frame[3].
    ONLY if you are running Outlook against Exchange online (Office 365) select Exchange Type: Online radio-button in the Mode frame[3].
    Now click Apply button. You will see the following warning: “The operation you selected will not complete until you quit and restart Microsoft Outlook.” Click OK button. Exit Outlook and restart it. Make sure that Identities list is still populated.

  5. [Skip this step if you run SmartReply 2010 ver or newer.] Select File > Options > Advanced (1). Click Send/Receive… button (2). Select All Accounts in the list (3). Click Edit button (4). Select each account that has been created by SmartReply (5) and uncheck “Include the selected account in this group” checkbox (6). If you are not sure which account to disable, click “account Properties…” button (7). All accounts created by SmartReply have “none” in “Incoming Mail Server” and “Outgoing Mail Server” fields (8).

    Click OK button to close “Send/Receive Settings” window. Click Close button to close “Send/Receive Groups” window. Click OK button to close “Outlook Options” window.

  6. Navigate to Inbox folder. Click View (1) > “View Settings” (2). Click Fields… button (3). Select “All mail fields” (4) from the list on top left corner of the form. Select “E-mail Account” and “To” fields in “Available fields:” list and press Add button. Make sure these fields are in the right list now (5).”

    Click OK button to close Show Columns window. Click OK button to close “Advanced View Settings” window. Now you see “E-mail Account” column in the view (6).

    Navigate to Sent Items folder and perform the same procedure.


  1. Open Outlook and create a new message. Click From button and select a non-default account (identity) from the list. Place any address you can control in To: field. Fill out Subject and message body. Send the message.
  2. Navigate to Sent Items folder and find a message you just sent. Look at “E-mail account” column.
  3. (We assuming that ChooseFrom utility is running properly on your Exchange server.) On the receiving side open the message you just sent and check it’s Internet headers.
    The screenshot shows how the received message Internet headers look in Outlook Express program.
    Make sure the From field contains the same identity that you have used initially (1). Note that ChooseFrom does not change the “Return-Path: header (2).

    Reply to the message.

  4. In Outlook navigate to Inbox folder and find a message you just sent. Look at “To:” (1) and “E-mail account” (2) columns.

    Click Reply button. A new message will appear. Note that the proper From: value is pre-selected (1).

SmartReply 2010 has been tested with Outlook 2010/2013/2016/2019 32-bit and 64-bit versions.


  1. Run Outlook and select File > Options > Add-ins. Click “Add-in Options” button. Select SmartReply tab.
  2. Click “Clear” button to clear the list of identities. You will see the following warning: “Are you sure you want to delete all custom identities?”. Click Yes. Click Apply button. The warning window “The operation you selected will not complete until you quit and restart Microsoft Outlook.” will appear. Click OK button.
  3. Restart Outlook and make sure that Identities list contains only primary (and secondary, if any) mailboxes. Exit Outlook.
  4. Select Start > Control Panel. Select Programs and features. Select SmartReply2010 in the list. Right-click and select Uninstall. Follow the instructions.

About this demo version

This demo version of SmartReply utility is fully functional, but will show a splash screen when it loads.


Q. I get error messages when receiving mail. All of the alternate addresses show a message saying “Receiving reported an error, 0x08840900: The server name you entered cannot be found on the network (it might be down temporarily). Please verify that you are online and the server name is correct”. I actually get mail, but these messages will be disturbing to other users. What’s the matter?
A. You should perform step #6 of Installation section to exclude the fake accounts from Send/Receive group.

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.

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