Switching from POP email to Exchange
December 29, 2006 1:35 AM   Subscribe

We're making the switch from POP mail to hosted Exchange mail, and it isn't as much fun as it should be.

Our pop mail host had become undependable over time. Along with switching providers, we decided to switch to a hosted Exchange solution. I figured mail is mail, so I probably didn't do as much upfront legwork prior to signing up for the new service (with Mi8) as I should have. Now I'm knee deep in making the transition from POP to Exchange work and am having difficulty getting off the line with it.

The first challenge is making it work with Mozilla Thunderbird. I realize Exchange is made to work with Outlook, but one of the owners of our company likes and uses Thunderbird, so I need to make the effort. It doesn't help that he's out of town until next week, so it's dangerous for me to make an arbitrary switch to Outlook on his PC. I've managed to configure Tbird to retrieve incoming mail, but haven't cracked the outgoing settings. Most of what I've found via web search says you need to use a separate SMTP server for outgoing mail if you're using Thunderbird, but I need to verify this. Mi8's response is they only support Outlook, and they're not even willing to point me to other resources. I wish I had known that before signing on with them.

The second problem I'm faced with is understanding a basic concept of Exchange. Using Outlook with POP you are given the option to leave messages on the server or automatically clear them after X days. To simplify matters, all of our users' Outlook settings delete messages after 5 days and the users archive the inbox on their own. As everybody here lives in email and needs to keep old messages, they've ended up with archives going back a few years resulting in many large (+1gb) PST files, so keeping messages on the server for any length of time isn't practical (or economical). I cannot find IMAP settings in Outlook that will automatically delete messages from the server. Is the assumption with exchange that you use the server to store all of your messages, or that you will manually archive them off? Also, Mi8 provides software called fastinstall that creates Outlook settings to connect with their servers. Unfortunately, it accomplishes this by setting up a new profile in Outlook that doesn’t let you mingle your old mail with the new. If I manually set up the Outlook clients, is there a reason I can’t just add the Exchange settings as a new email account in the existing POP profile?

And finally, does anybody have any good public web resources for Exchange administrators?
posted by SteveInMaine to Computers & Internet (4 answers total)
With Exchange and IMAP you are actually looking into the folder on the server when you view your messages, as opposed to POP which downloads a copy. This is why there's no option to leave a copy on the server.
posted by kenchie at 2:01 AM on December 29, 2006

AFAIK, the only clients that work completely (or, at least, adequately) with Exchange are Outlook, Entourage (Mac) and, of course, OWA.
Wouldn't it be easier to simply switch to a more dependable POP host?
posted by Thorzdad at 4:48 AM on December 29, 2006

Best answer: For your first challenge of getting Thunderbird to send mail, Exchange servers are often configured as SMTP servers, if this one isn't then you'll need to use another SMTP server - your ISP almost certainly has one that you can use (although with a laptop you'll run into problems that when connecting via a different ISP, eg at home, you'll need to use a different SMTP server). Thunderbird definitely works with the more vanilla parts of Exchange - I used it several years back without problems - if you start setting up Public Folders with non-mail contents then it can start to get a bit odd since Thunderbird attempts to render the calendar entries as IMAP mail but it's not an insurmountable issue.

My Exchange knowledge is a little rusty on the second issue but I can at least give you some pointers: The Exchange mailbox is always on the server and can be synchronised with the client (using OST files for offline working) or just accessed online like an IMAP system. What you probably want to set up (and you'll need to find details of how to do this) is local PST files on user's machines and a setting to archive mail beyond a certain age to the local PST file. This runs the risk that mail can be lost if a user's machine dies but it means that more mail can be stored more economically.

For your third issue, I'd recommend some experimentation - I believe that you should be able to set up Exchange account settings in your pre-existing profiles but you might have to deal with a few additional issues like checking which mail boxes mail goes into and is sent from that can be painful.

I can't recommend any Exchange resources as I managed to escape Exchange management a while ago and haven't looked back, not to be too snarky but I think you really should have checked what you were getting yourself into before deciding to move to Exchange - it's a far more complex beast than straightforward POP3 or IMAP are - if used correctly across your organisation then some of the group working features can really be useful but you'll need to persuade your Thunderbird users onto Outlook to get the benefits of those features (or OWA may now support them well enough to make that a viable alternative).

Good luck.
posted by koshmar at 5:34 AM on December 29, 2006

Best answer: Exchange is considered to be more complex than your typical mail server, and there's very good reason for that: it's not a mail server. It's a collaboration platform that also includes e-mail. That being said, it's pretty straightforward for setup and maintenance. In every environment I've used it, including my current 13,000 user environment it's been "install and forget". The fact that they're doing all the backend stuff will make your life easier once you get used to it. I guess what I'm saying is to not panic, it's really not that difficult. :)

To address your specific questions: If they've set it up to give you the option, you can setup Tbird to use it as an IMAP server, which will give you some of the functionality of using Outlook as a client. As another poster mentioned, your ISP will need to provide you with an SMTP server that they provide (most likely the same machine Exchange is hosted). As koshmar mentioned, he might have problems if he's on the road and using a personal ISP to connect up. But, that's also a question for your Exchange host.

To get the users old mail, simply open them up in Outlook. File -> Open -> Outlook Data File and open the old PST. It'll be "connected" at the bottom of their folder list and show as Personal Folders. However, if their mail is that big, you should probably have a class with your users on how to properly use e-mail. I used to have a couple of multi-gig PSTs that contained my personal mail from numerous accounts going back 14 years. Yes, 14 years. I used a tool that went in and removed all attachments and I ended up with one 50M PST that contained all the mail. Show your users how to share files on a local file share and send links to each other and your mail usage will decrease dramatically. There's no reason a typical end user should have larger than a 100M mailbox unless they're using their mail wrong. Management and salespeople, however, are a whole different breed. They can't be taught, so just give 'em what they ask for. As long as the rest of the userbase isn't being pigish, you should be able to provide.

The best resources online for Exchange admins are SlipStick and msexchange.org. Spend enough time there, and you'll learn to love Exchange as I do and not become jaded like koshmar. j/k! :)
posted by Spoonman at 6:31 AM on December 29, 2006

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