Before I start and/or you start reading let me disclaimer this entire post.
"I understand best practices of Exchange and of Outlook client - If a client asks you for a specific thing that "always worked before" then you would also try to get a solid answer. OK That being said here goes the question.
I have a client that was in business with online media about 4 years ago. He had a vast infrastructure, around 60 employees and over 50 off-site servers for various tasks. After the collapse of the economy he lost everything.
When I met him he had a single desktop running XP Pro. That machine had crashed trapping all of his Email. I rebuilt the machine as a VM and mounted it with Acronis. I used a tool I built to scan the entire PC for .PST files and export to a central location on a NAS I had. Come to find out there was 17 POP (Netsol) email addresses in that outlook 2003.
He is the only employee now and wants to send AS (not on behalf of) all of these 17 email addresses. I told him, no problem just change the From: field in outlook to send AS the address you want.
****He told me that he never had to do this before, that when he got an email he just hit reply and it would go out as the person that was the original recipient. ****
I moved him to Office 365 and began importing all the old mail into a single profile. After a few days of sync time I asked him to check the email and see if all of it was there. Sure enough it was missing 2010 - 2011 and skipped right to 2012 -2013 with some (about 400 messages) being from 2008 - 2009.
I told him after lots of probing that he would need to get an account for every mailbox he wanted to send from. He agreed to this again stating the above that he never had to type in an address to send as before.
So here is the problem base:
He has the following folder structure in Outlook 2010 currently and it works.. sorta.
1. Domain 1
a. address@domain1.com
b. address2@domain1.com
c.Address3@domain1.com
2. Domain 2
a. Address1@domain2.com
b. address2@domain2.com
and so forth and so on for 17 email address.
I have created SendAs perms with PowerShell and forwarders for all accounts to the others both ways. i.e. Address(@)Mailaccount1.com can send as Domain 2 and so forth across the board.
Last night he asked me to add a new address, so he could send AS and I opened outlook to find only 10 addresses on the From drop down.
I REALLY need to figure out how to make it like it used to be for him. Get a mail to address one while the profile is address 2 and send AS address 1 always without having to choose the address.
I am curious, is there a way to parse the original message recipient using a connector in exchange so no matter what email address he sends from it will ALWAYS reply as the original recipient?
Thanks, sorry its so confusing.
Josh