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I have multiple email accounts, with different organizations, on different servers. I presently manage them as POP3 accounts with Outlook 2010 (Windows) - but switching between machines is becoming a problem for me. This suggests switching to IMAP. The problem is that I have a many-to-many relationship between email account and project. My Outlook folder structure is project-based. (I use one Outlook file for all accounts.)

If I switch to IMAP, the top-level of my (logical) folder tree will be account based, correct? This is not so good. The only work-around I can think of is to set up another IMAP account (maybe gmail), push my Outlook folder structure onto it, and use that as a repository, dragging emails from other IMAP accounts onto it as required. I think this will work...

Any other suggestions?

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Why are you "switching between machines"? Outlook lets you have several accounts, each one whatever you need (POP3, IMAP or Exchange), and can retrieve mail from all of them without you having you having to do anything special. You can also define rules so that mail arriving on different accounts gets moved automatically into different folders. When you reply to a mail, it goes out (by default) on the same account as it came in on. –  Nicole Hamilton Mar 5 '13 at 22:43

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