Let me put my cards on the table, without saying too much beyond the obvious. When Gmail began in 2004 as a public beta, where you had to be invited to sign up, I decided to give it a try. Now the same was true with Hotmail, AOL and other services over the years. I always wanted to get in early and grab the best names, and I was mostly successful.

However, my uses for Gmail were pretty basic. I simply wanted to send and receive email without any red tape. When Google added IMAP support, it made it possible to use a regular email client, such as Apple Mail, without having to contend with the busy online interface and the targeted ads. Indeed, I seldom run any Webmail, unless I’m using someone else’s computer.

Even when Gmail exited the beta stage, there were loads of organizational and feature options, some beta, some release, which made it endlessly confusing. While power users may have cherished the features, most people didn’t need them.

One particularly irksome programming decision was to organize mail in a single category, All Mail, and use flags to separate messages that you wanted to put in other categories. In normal email systems, you’d deposit messages in a special folder. With Gmail, applying a flag or label simulates a folder, which means you can take a message and have it spill into multiple categories. You may compare this to the OS X Mavericks Finder, where you can use the new tagging feature to organize your stuff when a simple folder isn’t sufficient.

Now when Gmail began to support IMAP, which is when I began to use it more extensively, they had to force their unique interface to match the tried and true. So folders would be used to separate flagged messages, to make everything appear the same as other email systems.

I don’t want to confuse you any further. Let me just tell you that Gmail worked all right for the most part in Mail, except for being unable to undo a mistakenly deleted message, as you can with most other email systems. Instead, you go to the Trash, although, technically, Gmail doesn’t normally delete messages unless you specify that option.

In any case, there have been complaints that Mavericks Mail is not as Gmail friendly as earlier OS X versions. In recent days, I’ve read some articles from Gmail users who have opted to take their business elsewhere. I even saw one on how to switch from Gmail to Outlook. No, not the Outlook email client from Microsoft, but the Outlook.com free mail service that replaces Hotmail.

Now I never paid much attention to Hotmail/Outlook.com until Microsoft added IMAP and ActiveSync support. That’s when things changed. The new online interface is predictably minimalist, echoing the Metro or Modern UI look and feel that has polluted Windows 8. But it’s not so bad online. Targeted ads are presented on the right pane, although a $20 annual payment will dispatch them for good.

I oped to add my Outlook.com account to Mail. Apple has clearly worked with Microsoft, as the setup was nearly automatic.  On iOS7, you merely have to give your username and password, and it’ll be set up as an Exchange-style account, complete with genuine push email. That means that, when a message arrives, it’s dispatched to your iPhone or iPad likety split.

Typical of Microsoft’s minimalist approach to consumer services, there are no tricks about Outlook.com email. You have a straightforward online interface, so configuring it for your Mac, PC, iOS or Android device is a snap relatively speaking. Moving from Gmail is fairly simple. First set a forward from your Gmail account to your Outlook.com account, and you can also manually copy your messages from Gmail’s IMAP folders to the corresponding folders in your Outlook.com account; that is, if you want everything in the same place. Outlook.com even has a send-only feature, where you can actually send your messages through your Gmail account, simply by entering your username and password. Gmail’s two-factor authentication feature has to be switched off, though.

In terms of features, you can set up a multi-gigabyte account at Outlook.com, although Microsoft is a bit vague as to total capacity. I’ve heard 5GB and 10GB, and another version where your mailbox expands as needed, until it stops, after which you have to clean out older messages. Go figure.

Update: Although not widely advertised, it appears that Yahoo! Mail does have IMAP support, apparently in the business version. However, the documentation I’ve seen seems to confuse IMAP with ActiveSync. But since I only check my Yahoo! account on a rare occasion, it really doesn’t matter.

In any case, after nine years with Gmail, I’ve moved over, partly as a test, strictly for my second-level email. The rest still comes through my domains, as before. You also have to wonder whether you can depend on a free email service, and whether Microsoft will just up and give it up some day, or decide to charge you extra for IMAP support and other features. When you use an email client, you’re not seeing the ads, but maybe Microsoft wants you to feel warm and fuzzy about the products, and I can see where that’s a plus.

But I’m especially intrigued by the ability to send out email through another service from Microsoft’s interface. Imagine doing that with Gmail. Ah, the unkindest cut of all!

This article was posted on Friday, November 1st, 2013 at 12:00 AM and is filed under News and tagged with: Android, Aol, email systems, Gmail, Google, Hotmail, Imap, iOS, iPad, Iphone, Mac, Mac Os X, Mail, Microsoft, OS X Mavericks, PC..