IvaSoft - ChooseFrom application allows users to send from an additional Exchange address/alias

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 john.doe@companya.com primary SMTP address and john.doe@companyb.com secondary smtp address. John Doe can easily receive the message addressed both to john.doe@companya.com and john.doe@companyb.com, but he can not send the message as john.doe@companyb.com 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.

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:aaa@bbb.ccc' 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.

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.

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.

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.

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 updated 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.

Do you want to send from your Exchange account using any of your proxy SMTP addresses?
Ønsker du at sende fra din Exchange-konto ved hjælp af en af dine proxy SMTP-adresser?
Você deseja enviar a partir da sua conta Exchange usando qualquer um dos seus endereços de proxy SMTP?
Souhaitez-vous envoyer depuis votre compte Exchange en utilisant l'une de vos adresses proxy SMTP ?
Wollen Sie von Ihrem Exchange-Konto mit einer Ihrer Proxy SMTP-Adressen senden?
¿Desea enviar desde su cuenta Exchange utilizando cualquiera de sus direcciones SMTP de proxy?
Vuoi inviare dal tuo account Exchange utilizzando uno qualsiasi dei tuoi indirizzi proxy SMTP?
Wilt u met elk email addres van uw Exchange account email kunnen verzenden?"
How can I use an alternate address with Exchange Server?
How to Send E-mails with Exchange Using a Different “From” Address?
Exchange: How can you use an SMTP address other than your default reply-to from Outlook?
Secondary Email Addresses
smtp alias Office 365
Exchange Server and Secondary Email Addresses
How To Easily Change a User’s Exchange Server Alias and Display Name
PR_EMS_AB_PROXY_ADDRESSES
proxy SMTP addresses
alias SMTP address
SMTP
TLS
SSL
backlink from https://www.msoutlook.info/question/send-mail-from-additional-exchange-address-or-alias
Send mail from an additional Exchange address or alias
I’ve got a single Exchange mailbox which holds multiple email addresses. I can receive mail sent to any of these addresses just fine, but I cannot find a way to choose which address to send out with.
I’ve tried setting the From field with another address but that got automatically replaced with my default address or a bounce message saying that I don’t have permission to do so.
How can I send out a message with one of my mailbox aliases?
Outlook solution 1: POP3 dummy account
Outlook solution 2: Proxy Manager Add-in
Exchange solution 1: Alias via an AD Contact or Distribution Group
Exchange solution 2: ChooseFrom and SmartReply tools backlink from https://www.howto-outlook.com/faq/aliases.htm
Aliases on Exchange mailboxes
Method 1: Configure an Active Directory Distribution Group with your alias
Method 2: Use the Proxy Manager add-in
Method 3: Use the ChooseFrom and SmartReply add-in
backlink from https://exchangepedia.com/2007/04/how-to-send-as-alternate-email-address.html
Send as alternate email address in Outlook and Exchange
Workarounds for sending mail using a proxy address
1.Using additional mailbox or recipient(s)
2.Using SMTP clients
3.Using Address Rewriting
4.IvaSoft ChooseFrom – an Exchange Server add-on
5.Proxy Manager – an Outlook add-in
6.Exclaimer Email Alias Manager for Exchange



	You can add the display name:

Examples:

	You can add the display name: