When it comes to e-mail, there’s no such thing as a one-size-fits-all solution. I’ve learned that lesson emphatically over the last year as I’ve tested a variety of different e-mail solutions for myself and for various friends and clients.

The top-secret Technology Reviewers Handbook says that after all that evaluating I’m supposed to pick a winner. But there is no clear winner. Instead, I’m happily using three different e-mail systems:


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    My business e-mail i running on a hosted Exchange account at Intermedia. My wife’s business account is hosted on the same server. (I’ve written previously about my reasons for choosing Exchange 2010; I switched to Intermedia earlier this year because they offered Exchange 2010 when other hosted Exchange providers were still offering Exchange 2007.)
I have a single user account at Office 365 for several upcoming projects, where features other than e-mail were the deciding factor.
I’m playing Google Apps administrator for an out-of-state client who needed a free, easy e-mail solution that would work well with his new Android phone.

Why three different solutions? Because each client (including myself) had different needs. I sorted them out by asking a series of questions and thought it might be useful to share my decision tree here.

A note: If you live in the United States, your options should be the same as the ones I write about in this post. In other countries, some services might not be available, and others might be offered at different prices. In addition, I do not cover the many educational offerings available for students and others associated with an educational institution.

1. Do you want a store-and-forward server or one that syncs your messages in the cloud?

Most Internet service providers offer POP3 mailboxes. They’re usually a standard feature with cheap web-hosting plans, too. These accounts use store-and-forward servers that assume you’re downloading your messages to a local store and deleting them off the server immediately. The server isn’t designed to keep an archive. Your master copy of any message is local.

By contrast, cloud-based mail products store your messages on a server so that you can access your e-mail—all of it, new and old—via a web browser. You can usually sync the server’s message store with a local PC or device, using Exchange ActiveSync or IMAP.

For this question, I think there’s only one correct answer. If you work in a big corporation, a central server that stores every user’s messages is a key part of a legally acceptable archiving policy. But a cloud-based server is also a good idea even if you’re a one-person organization. If you have more than one device (smartphone and PC, maybe a notebook, maybe a tablet), keeping everything in sync with a POP3 account is impossible. I still have a few POP3 accounts associated with some domains I own, but I forward all incoming messages from those accounts to a cloud-based account.

2. Do you need a custom domain?

I’m a firm believer in owning your own domain—especially for business mail. You might be perfectly happy to use a generic webmail address as your calling card to the rest of the world. (Just don’t adopt an address from your ISP as your primary e-mail account. If you move or change service providers, that address will become useless.)

The free Google Apps offering allows you to assign your custom domain to Google Apps. Hotmail offers this feature, too, but the domain management tools in Windows Live Admin Center made me want to scream in frustration. For my out-of-state clients, it took a few hours to get their custom domain working with Google Apps, but after those initial hiccups were out of the way it’s been problem-free.

Naturally, all of the paid services—hosted Exchange, Office 365, and Google Apps—offer excellent integration with custom domains. For Office 365 and Intermedia, I had a choice of turning an entire domain over or just defining mail exchange (MX) records. If you know your way around DNS configuration, this is a straightforward task. If you don’t, be prepared to ask for help (or take a crash course in DNS management).

Here’s the DNS manager for an Office 365 P plan. Note that you must set up the MX records with an external DNS service and can’t edit them here:

And here’s the custom DNS manager that Intermedia customers find in the HostPilot control panel:

3. Do you plan to use Microsoft Outlook?

If you live in Outlook, then your primary account should be on an Exchange 2010 server. Period. Full stop.

The combination of Outlook and Exchange offers great online and offline support. That’s true whether you’re using Microsoft’s Office 365 or a hosted Exchange option like Intermedia’s. Hotmail accounts work well after you install the Microsoft Outlook Hotmail Connector.

My experience with accessing Gmail and Google Apps accounts via Microsoft Outlook has been consistently bad—so bad that I won’t use the two products together. I won’t recommend that combination for anyone else, either. If you have a Gmail account and you want offline access, you can use the Offline settings in Google’s Chrome browser or try a third-party client program other than Outlook.