Answering from second email address

Click Options in out look when sending a message. Choose the "From" uption under show fields. You can switch between them there :)

Note you need to have a new email open to see the option tab.

Only way I can think of is a work around. Add pop or imap account, and have it point to an SMTP server you have access to.
Sending from a different account involved the Send from this account button.
Using above answer (using from: field) ONLY works when the mailbox is not the same user (since both are jonny, I suspect it's one mailbox)

The only way you could do it is if you have two mailboxes with different email addresses where user have privileges to both he/she could choose which mailbox to send email from.

Unfortunately not. You can receive on multiple SMTP addresses but you can only have 1 default address and you cannot manage this using the From: field in Outlook.

Whatever the Primary SMTP Address is set to at the time is the only address you can reply with.

Will.

So the only option is to create Jonny-fake account?

If you want to send out Emails using 2 different Primary SMTP addresses then you will require 2 mailboxes period. You cannot do this from a Single Mailbox with multiple Email Address.

There is no way around this. However what you could do (it is a little messy) is the following
- Mailobx1 = joe@abc.com
- Mailbox2 = joe@xyz.com

Mailbox1 is the Primary Mailbox Joe wants to use.
Provide Mailbox1 Send As Permissions on Mailbox2
Setup Forwarding on Mailbox2 account to forward all mail to Mailbox1

That will allow you to use the From: and Send As Mailbox2 but you will still receive Mailbox2 Emails into Mailbox1.

This is the only work-a-round that i can see working.

Will.

I like tigermatt solution.
I still need to make fake pop account in Outlook but no mess with user accounts in AD.
Thank you!