How to change to an alternative address for sending email from Outlook?

This user has multiple email addresses in his Exchange mailbox account. One of them is Primary email address while others are alternative. My question is, how to change to use other alternative email address in FROM while sending an email from Outlook?

P.S. I understand I can use Delegate email account and change the FROM address to it but it is not what I'm asking for.
CastlewoodAsked:
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Brian BEE Topic Advisor, Independant Technology ProfessionalCommented:
You'll have to set Outlook to show the "from" line so you can change it when you send a message.

If you are talking about Exchange accounts, the user will also need to be given "send as" permissions so they can use other people's names.
CastlewoodAuthor Commented:
I know how to have the 'FROM' showing up but it only allows the email addresses you are delegated to. Again, my question is, how to change the FROM to one of the alternative email addresses of the same email account?
Zacharia KurianAdministrator- Data Center & NetworkCommented:
Well, there is no native way to choose which one of your Exchange mailbox addresses/aliases to use when sending out an email.

The outgoing address that will be used will be the address that has been set as the “Reply address” for your user account by your Exchange administrator.

Zac
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Zacharia KurianAdministrator- Data Center & NetworkCommented:
May be you could setup a dummy pop3 and setup one of the address as the default reply

Zac
Brian BEE Topic Advisor, Independant Technology ProfessionalCommented:
Sorry I misunderstood. They have multiple addresses on one account? No built in way to do that. It will always default to the reply-to address.

POP3 as above would work, otherwise you'd have to set up separate mailboxes.
Alexei KuznetsovMicrosoft Outlook MVPCommented:
Sorry, no way. I can recommend the following:

1. Create a separate Exchange Contact with external email address for each required FROM in your Active Directory.
2. Give the user Send As permissions for that contacts.
3. Now the user can select these AD contacts as FROM.

This is the way our company using multiple FROM in Outlook.

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CastlewoodAuthor Commented:
But we want the replied emails to be sent to this user's email account instead of to the contact. How to do that?
Alexei KuznetsovMicrosoft Outlook MVPCommented:
This is exactly how it works. The email will go from the user's email account (because Contacts are not Mailboxes). This is why Exchange contacts are the best way to select FROM in Outlook.
CastlewoodAuthor Commented:
Alexei,

The problem is, the replied emails will go to the external mail box rather than this Exchange mailbox, correct? How to resolve this ?
Alexei KuznetsovMicrosoft Outlook MVPCommented:
There is no problem here. Contacts are not mailboxes. Emails will come to this mailbox as required (because of additional proxy addresses).
Brian BEE Topic Advisor, Independant Technology ProfessionalCommented:
I think what Alexei is saying, is since a contact can't receive mail, Exchange will look for a mailbox with a matching address. So you get the best of both worlds. A clever idea, actually.
CastlewoodAuthor Commented:
Need to use Distribution Group instead of Contact so the incoming emails can flow into this user's original email account.
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