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SmartReply 365 for Outlook
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Updated:
9 February 2026

SmartReply 365 is a utility for Outlook desktop (Windows) users who have enabled the Microsoft feature to send emails from an alias in Office 365.

This utility will automatically populate the proper From: address when you reply to or forward a message received as an alias address.

In other words, if you get a message addressed to jdoe_alias@contoso.com and click the Reply (Reply All, or Forward) button, the reply or forwarded message will have jdoe_alias@contoso.com in the From: field.

In addition, SmartReply 365 can assign different signatures to different aliases.

SmartReply 365 diagram

The application is a COM add-in. It is compatible only with classic desktop Outlook for Windows.
 
It is not compatible with the new Outlook for Windows.

Outlook - Classic vs New

Current version: 1.0.21

Installation

  1. Download the SmartReply365-Demo.zip archive to any folder on your workstation. Extract all files, then run SmartReplySetup.exe and follow the instructions.
  2. Run Outlook. Select File > Options > Add-ins and make sure that SmartReply 365 exists in "Active Application Add-ins" list.

    SmartReply 365 installation - picture #1

Testing

  1. Open Outlook and reply to any message sent to your alias address. Make sure that the reply has your alias address in the From: field. Send a message.

    SmartReply 365 testing - picture #1

  2. Navigate to Sent Items folder and find a message you just sent. Make sure the From: field contains your alias address.

    SmartReply 365 testing - picture #2

  3. Click File > Options > Mail > Signatures. Create four different signatures and name them "DefaultSigNew", "DefaultSigRF","Alias1SigN" and "Alias1SigRF". Set the signature for new messages to "DefaultSigNew" and the signature for replies and forwards to "DefaultSigRF". Click OK button.

    SmartReply 365 testing - picture #3

  4. Click File > Options > Add-ins > Add-In Options. Select "SmartReply 365" tab. Click on the topmost alias in the list ("alias1@testivasoft.com" in the screenshot). Using drop-down lists, set the signature for new messages to "Alias1SigN" and the signature for replies and forwards to "Alias1SigRF". You will see the text previews of these signatures in the appropriate text boxes. Click Apply button. Click OK button to exit Options.

    SmartReply 365 testing - picture #4

  5. Create a new message and select an alias in the From: field. Make sure the signature is changed.

 

Uninstallation

Click Start > Control Panel > Programs and Features or go to Settings > Apps > Installed Apps. Select SmartReply 365 in the list. Right-click and select Uninstall. Follow the instructions.

SmartReply 365 uninstallation


 

About this demo version

The SmartReply 365 demo version adds the phrase "[SmartReply 365 DEMO]" to the subject line of each message sent from the alias address.

 

Pricing & Licensing

Licensing policy: The product is licensed on a per-user basis.
All transactions are securely processed by our payment providers.

License type
Price per unit
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Single license
$35.00
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Site license
$1,500.00
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Enterprise license (including the source code)
$4,500.00
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