Apple Mail behavior when replying to mail sent to specific account

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Hi, first post here. I just got my first MacBook Pro after I was issued a MBP by my new employer (eek, can you say "sink or swim"?) My old Windows laptop was showing signs of serious problems, so I decided that since I had to learn to use a Mac for work, total immersion was the best idea. My new MBP is running Lion.

So far, the transition has been going reasonably well, but I have a baffling issue with respect to Apple Mail.

I've used Outlook for my personal email for years, using a hosted exchange service running Exchange 2010 (with ActiveSync, which I added when I bought an iPad). My current cell phone is a Blackberry, so Exchange works nicely with it. I have Outlook 2011 for Mac on my work MacBook, but there are several ways in which it behaves differently from Outlook 2010--and not in a good way--mainly in where you can have the mail delivered. I always had all of my Windows Outlook mail delivered to my Exchange inbox. I use several different pop accounts, all of which I directed to deliver to the Exchange Inbox. That way, all of my mail is kept on the Exchange server, which is what I want. I found that with Outlook 2011 for Mac, even if I set up a rule sending my incoming mail to the Exchange inbox, if I hit "reply" it invariably used the Exchange email account to send. (NOT what I want--I want to "reply from" whichever account the mail was sent to).

After struggling with it a bit, and deciding I did not want to run Parallels constantly just to have Outlook 2010 running, I decided to try the Apple Mail app. After tinkering a bit with the rules, I finally got Apple Mail to direct the mail where I want it to go (the main Exchange inbox or one of the Exchange folders I have set up). And the reply would be sent from the account to which the original email was sent.

Or so I thought. Oddly, any email sent to "account x" (a pop email account), which is directed by rule to the main Exchange folder, behaves the way I want it to. Invariably, if I hit "reply" to such an email, it is sent from "account x". So far, so good. Unfortunately, if the email sent to "account x" is directed to a subsidiary Exchange folder, half the time a "reply" will be from "account x" and half the time it will be from the Exchange account.

This seems to be completely random. I can find no consistency or pattern to which email will be used as the "from" address. At first I thought perhaps it depended on when the email downloaded, or whether the email had already been directed to the subsidiary folder by my Windows laptop (I turned off Parallels while I was experimenting with this). I stopped retrieving emails on the Windows computer, as well, but the behavior persists.

I know this is a very arcane issue, and I am probably the only person in the world who has this kind of setup or is trying to make this happen, but it is driving me nuts. And, yes, I know I can select which account to send "from" at the time I send the email. The problem is that I often forget to do that, and I suspect sometimes it has caused certain of my emails to wind up in someone's spam folder. And certain forums where I post will only accept email from the registered address.

Sorry for the lengthy post, and I appreciate anyone who took the time to read it and think about it at all. Anyone have any ideas/suggestions?
 
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Oct 15, 2012
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How tu setup mac mail (Version 4.6 (1085)) into Outlook 2010

I already had my Imac and Macbook configure to use Windows 7 with VM ware, I just finished installed Microsoft Office 2010 and I'm trying to setup Mac mail into Outlook, but I couldn't do it. Googled it, etc.
Can anyone can help me with this matter.
Thanks in advanced,
Andreniko
 

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