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SmartReply 365 for Outlook

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Updated:
9 February 2026
See also:
Sending From Email Aliases - Public Preview

Purpose

SmartReply 365 is an add-in for Outlook users who have enabled the Microsoft feature to send emails from an alias in Office 365. This add-in automatically populates the proper From: address when you reply to or forward a message received at an alias address.

For example, if you receive a message addressed to jdoe_alias@contoso.com and reply, Reply All, or forward it, the outgoing message will have jdoe_alias@contoso.com in the From: field.

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

SmartReply 365 flow overview diagram

The application is a COM add-in compatible only with classic desktop Outlook for Windows. It does not support the new Outlook for Windows. Comparison of classic Outlook (with add-in support) and new Outlook for Windows

Current version: 1.0.21

Installation

  1. Download SmartReply365-Demo.zip, extract all files, then run SmartReplySetup.exe and follow the instructions.
  2. Run Outlook. Select File > Options > Add-ins and verify that SmartReply 365 exists in the "Active Application Add-ins" list.
    SmartReply 365 listed in Active Application Add-ins

Testing

  1. Open Outlook and reply to any message sent to your alias address. Verify that the reply has your alias address in the From: field before sending.
    Replying to an alias address in Outlook
  2. Navigate to the "Sent Items" folder and locate the message you sent in step 1. Verify that the From: field contains your alias address.
    Sent message showing alias address in From field
  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.
    Creating and assigning signatures in Outlook settings
  4. Click File > Options > Add-ins > Add-In Options. Select the "SmartReply 365" tab. Click 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". Text previews of the selected signatures appear in the appropriate text boxes. Click Apply. Click OK to exit Options.
    Setting alias-specific signatures in SmartReply 365
  5. Create a new message and select an alias in the From: field. Verify that the signature has changed.

Demo Version Notes

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

Uninstallation

You can uninstall the add-in via Settings > Apps ("Installed Apps" in Windows 11, "Apps & features" in Windows 10).

Pricing and Licensing

This product is licensed per user.
Payments are processed by PayPro Global. For payment-related support, contact PayPro Global Customer Support.
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
$4,500.00
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A Site license covers a single organization at one physical location, with an unlimited number of installations.
An Enterprise license covers all computers across a single organization worldwide, including all branches and remote users.

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