Hi Adam,
In SmarterMailo 16.x, we added an account setting for "Use To: address for replies". When enabled, replying to a message via webmail will use that email's To: field as the Send From address of your reply, regardless of whether the message was sent to your primary SmarterMail email address or a domain alias, email alias, SMTP account, disposable address or plus address. For example, if an email is sent to an alias you are part of, replies to that email via webmail will automatically use the email alias address as your Send From address. (This setting does not prevent you from manually changing the Send From address when composing a message.)
It sounds like you'll just need to head to Settings > Account Settings and enable "Use To: address for replies" on the Webmail card.
Andrea Free
SmarterTools Inc.
877-357-6278
www.smartertools.com