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I was hoping someone could chime in with some information or experiences with a email system.

I am working at a small business with about 25 users. We currently have a Windows Server 2008 R2 box acting as domain controller, and an email system that is simply a bunch of POP3 accounts. Everyone's computer runs Outlook (or Outlook Express, ugh) and downloads its email by itself.

My boss is doing a lot of travelling now and he's finding having to use remote desktop to view his email frustrating - he doesn't want his phone to download it from the POP3 server separately because then everything has to be organized twice.

I have a vague idea of how Exchange works and I know that it would centralize our email to our server. We could then use the Exchange web access and/or add an account to our smartphones to view our messages with the same folder structure/organization we see on our Outlook clients in the office (correct?).

The issue is that this costs time in setting up and mucking around with a complex piece of software on the server - Exchange. No one here has training for it.

Google Apps for Business seems like a good alternative, but then I also found out about Exchange Online (hosted Exchange), which has the same pricing as Google.

We're concerned about (1) getting our big blob of data to the server so there's no loss of archived email, and (2) we'd like to be able to back everything up every now and then in case the whole system just blows up. I'm also curious what happens when you lose your internet connection - does email just become inaccessible?

What are everyone's thoughts on this - what are the important points that I should use to decide?

If this is not an appropriate question for ServerFault, where should I ask? I'm not aware of any active discussion sites on the matter...

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closed as not constructive by mailq, Shane Madden, Zoredache, RobM, voretaq7 Dec 2 '11 at 3:44

As it currently stands, this question is not a good fit for our Q&A format. We expect answers to be supported by facts, references, or expertise, but this question will likely solicit debate, arguments, polling, or extended discussion. If you feel that this question can be improved and possibly reopened, visit the help center for guidance.If this question can be reworded to fit the rules in the help center, please edit the question.

    
If you can, then get out of the managing your own mail server. Running your own mail server is a PITA. The only reason to run it is if the security risk related to the cloud is important in your field because of regulator requirements, or some kind internal security requirements. –  Zoredache Dec 1 '11 at 21:39
    
Be sure to do extensive testing of whatever service you might want to migrate to. I have seen some very dissatisfied hosted Exchange customers. Some big-name hosted Exchange environments appear to be severely overloaded, to the point that e-mail messages sent to users within the same organization may take hours to be delivered. –  Skyhawk Dec 1 '11 at 21:53
    
Don't forget that Google Apps for Business can function as an Exchange server as far as Microsoft Outlook clients and ActiveSync mobile devices are concerned. If you are looking for a "hosted Exchange" option, it's worth evaluating Google Apps alongside actual hosted Exchange options. –  Skyhawk Dec 1 '11 at 21:56
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2 Answers 2

The key is this:

My boss is doing a lot of travelling now and he's finding having to use remote desktop to view his email frustrating - he doesn't want his phone to download it from the POP3 server separately because then everything has to be organized twice.

You really need to use IMAP for that use case. And if you don't have needs beyond email, then any mail server packages that or ISPthat supports IMAP will do just fine (Google Apps does support it, but you won't have to go with them for just that). Migrating the email could be simple as:

1) connect to the IMAP mailbox from the client. 2) copy files from the local folder to the IMAP folder.

It is when you need things beyond email (such as calendaring, tasks, etc) that the field narrows considerably. In that case, it would be appropriate to consider Hosted Exchange or Google Apps (provider supplied) or Exchange, Zimbra, Groupwise (if you are going internal).

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As a reseller of hosted Exchange, may I suggest hosted Exchange?

To address your questions:

1) That's going to be painful no matter what solution you use. Generally you'll setup Outlook (whether using IMAP for Google Apps or MAPI for Exchange), import your mail from PSTs, then wait for the exceedingly slow transfer process that will entail.

2) Users of Exchange with Outlook generally use what's called Cached Exchange Mode - basically your local computer has a complete copy of your mailbox that's on the server - so if the server were to die/go away/etc., you'd still have a copy of your mail. Note - IMAP does this as well. I just think Microsoft's implementation of it is a bit better.

As for differences between the two - generally Exchange's calendaring features are considered to be better than Google's, especially in terms of scheduling meetings with multiple users, allowing conference room booking, etc. Google is good, and getting better, but they're not there yet. I've also found Google's tech support for Google Apps to be worse than you tend to get from a good hosted Exchange provider. I know that as a provider we tend to do a lot of desktop Outlook support for our end users. Google only really supports the webmail interface. If you're heavy Outlook users, you will probably find Exchange to be better, at least in my experience.

In order to avoid the appearance of impropriety and shilling, I'm not listing my company here, and it's not in my profile, so I hope this doesn't look like a shameless attempt to grab money.

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