Chapter 4: Using Hotmail and Outlook.com

In This Chapter

Getting the scoop on Hotmail’s long and tortured history

Starting out with Outlook.com

Organizing Outlook.com

Finding out if Outlook.com went down

Getting some advanced Outlook.com tips

Two months before Microsoft shipped the original Windows 8, the folks in Redmond dropped a bomb on the online e-mail world. Hotmail — one of the best-recognized brands on the planet — would be put out to pasture, replaced by something completely different. Yes, Microsoft tossed out a brand as well known as “Coca-Cola” or “taxi” or “Visa” and replaced it with . . . Outlook.com.

If you think that the name Outlook.com was chosen because Microsoft’s new flagship online e-mail service-formerly-known-as-Hotmail looks or acts like Outlook in Office, or Outlook Express, or the Outlook Web App, or anything else that’s ever been called “Outlook,” you’d be wrong, of course. Outlook.com is just the old Hotmail, with a few internal changes and a new, Metro tiled-style boxy interface.

It’s all marketing, folks.

How thorough is the change? Well, right now, if you point your web browser to www.hotmail.com, you end up at login.live.com — the former Windows Live login location. (Windows Live IDs are now called Microsoft accounts, but whatever.) After you log in, you're directed to mail.live.com, which is the current home of what used to be Hotmail and is now Outlook.com — except it isn't really at Outlook.com. It's located at mail.live.com. And Microsoft is getting rid of the "Live" brand.

Doesn’t make any sense, does it?

In this chapter, I step you through Outlook.com, with a nod and a wink to Hotmail. If your old Hotmail account hasn’t been switched over to Outlook.com, log on to Hotmail, er, Outlook.com, uh, mail.live.com, and you’ll get to see the new interface.

Your mail hasn’t changed. Only the way Microsoft sells it has changed.

Getting Started with Outlook.com

If you don't yet have a @hotmail.com, @live.com, or @outlook.com e-mail address, getting one is easy. Follow these steps:

1. On the old-fashioned desktop, with your favorite web browser, go to www.outlook.com.

The main screen asks whether you have a Microsoft account.

2. To get a new Microsoft account, down at the bottom tap or click Sign Up Now.

The sign-up form appears, as shown in Figure 4-1.

3. Fill out the form creatively; type the CAPTCHA codes, if you can figure them out; deselect the Send Me Mail check box; and then tap or click I Accept.

Figure 4-1: Sign up for an @hotmail.com, @outlook.com, or @live.com e-mail address.

Part of the signup includes Microsoft’s two-factor authentication. In short, you are offered three ways to identify yourself: Provide a phone number where MS can send an SMS (text) message; provide an e-mail address where MS can send a verification email; and/or answer a security question of your choosing. Although the form doesn’t make it clear, you need to provide two of those three.

If you really don’t want to give Microsoft your phone number — I can think of about 100 million reasons why — skip the phone number question (yes, you can do that) and fill in an alternate e-mail address, and then answer a security question.

Microsoft doesn’t use any of those authentication routes right now, while you’re signing up. It’ll keep your answers and use them if you’re trying to retrieve your password.

In general, security questions can be hacked pretty easily. Having a phone number and/or alternate e-mail address on file with Microsoft makes it easier and more secure to reset your password if you lose it — Microsoft sends an SMS to your phone or an e-mail with a reset key. Only you can decide if the additional convenience (and greater security) of having a working SMS phone number or alternate e-mail address on file is worth the dent in your privacy.

Outlook.com whirrs for a minute or so and then shows you the Outlook.com welcome screen (see Figure 4-2).

That’s it.

Figure 4-2: Your new Outlook.com e-mail address is alive and working.

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You can now use your new Outlook.com account as a Windows logon ID. You can use it for e-mail, Xbox, just about anything. It’s just another Microsoft account.

Take a quick spin around Outlook.com, starting from the welcome screen, which you see when you log on to Outlook.com (www.outlook.com) using your favorite @hotmail.com, @live.com, or @outlook.com e-mail address (refer to Figure 4-2):

The default folders on the left are Inbox, Archive (which you may not be able to see, if you’re using an older account), Junk, Drafts, Sent, and Deleted. You click each folder to open it. Make sure you understand what each one is supposed to contain:

• Inbox gets all your mail as it comes in. If you don’t do anything with it, the message stays in your inbox.

• Archive is where you drag messages that you want to keep forever. Microsoft, uh, borrowed the idea of an archive from Google.

• Junk holds mail that was sent to you but that Outlook.com has identified as being junk. Outlook.com and Gmail have very effective junk identifiers, but occasionally a message will get tossed in here that really isn’t junk. If that happens, tap or click the box next to the “good” junk message, and at the top, choose Move To⇒Inbox.

You can also drag and drop the message into whatever folder you like.

If you get a piece of junk mail in your Inbox, don’t delete it. You can help the Hotmail filters and other Hotmail users by marking the message as Junk. Just check the box next to the message, and at the top, tap or click Junk.

• Drafts holds mail that you were working on but didn’t send.

• Sent contains copies of everything that’s gone out.

• Deleted is the place where messages go when you “delete” them.

You can create new folders. Just tap or click the New Folder link.

The search box in the upper left is the most important location on the Outlook.com main page. People go nuts trying to organize their mail. The Search function finds things amazingly quickly. But that’s the topic for the next section.

If you use the Windows Search charm while you’re in Outlook.com, the charm doesn’t search your mail: Search performs a Bing search on the entire Internet, not inside your mail. To look for mail, you have to use the Search box in the upper-left corner.

The Sweep feature enables you to move all the messages sent from a specific address into a folder. Select one message from the sender you want to move and choose Sweep⇒Move All From.

Outlook.com offers to move all the mail from the given address into a folder that you choose.

Similarly, you can delete all the messages from a specific sender.

Quick Views in the lower left enable you see only messages that meet specific criteria.

The Quick Views options are a little unusual. Here’s how they work:

• Documents: If you receive a message with a “document” attachment that Outlook.com recognizes — primarily Word, Excel, or PowerPoint documents — the message appears in the Documents Quick Views list until you delete it. Strangely, PDF files don’t qualify.

• Flagged: If you flag a message by clicking the flag icon, the message gets elevated to the top of your Inbox list, and it also appears in the Flagged quick view. There doesn’t appear to be any difference between looking at the list of flagged messages at the top of the Inbox and the list of flagged messages in the Flagged Quick Views category, and apparently you can’t assign different kinds of flags.

• Photos: If you receive a message with an attachment that Outlook.com recognizes as a photo, the message appears in the Photos Quick Views until you delete it.

• Shipping Updates: Arguably most bizarre of all, if an inbound message contains text that Outlook.com recognizes as a tracking number (UPS, FedEx, and so on), the message appears in the Shipping Updates Quick Views until you delete it.

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With the addition of a few obvious features that you see when you poke around — tapping or clicking a column heading, for example, sorts that column — that’s the extent of navigating in Outlook.com.

In the next section, I talk about organizing mail so you can use it effectively.

Bringing Some Sanity to Outlook.com Organization

Here’s my number-one tip for Outlook.com users:

If you have an Archive folder, don’t create any new folders.

That way lies madness.

Yes, you can create a folder hierarchy that mimics the filing cabinets in the Pentagon. You can fret for an hour over whether an e-mail about your trip to the beach should go in the Trips folder or the Beaches folder — or both. You can slice and dice and organize ’til you’re blue in the face, and all you’ll have in the end is a jumbled mess.

If you want to save that message about your trip to the beach, just drag it into the Save/Archive folder.

If you want to find all the messages about Trips, use the Search box. If you want to find all the messages about Beaches, use the Search box. And if you want to find all the messages about Trips and Beaches . . . wait for it . . . use the Search box!

People get caught up in flags (you can tap or click the silhouette of a flag next to a message to set it) as a way to organize and sort mail. If you work well that way, hey, knock yourself out. But note that there’s only one kind of flag; you can’t set up different flag colors as you can in many other e-mail programs. My general approach is to blast through e-mail as quickly as I can, responding to what needs responding and filing the rest immediately. De gustibus non est disputandum.

Handling Outlook.com Failures

Although any computer system in general — and any online system in particular — has failures, Outlook.com, and Hotmail before it, seems (at least to me) to be more susceptible than Gmail.

I recall one particular incident in January 2011, when Hotmail went down and took all the mail from 17,000 users with it. In the grand Hotmail scheme of things, 17,000 users is a very tiny drop in the 300-million-plus subscribers bucket. But if you’re one of the 17,000, your opinion may well vary. Ultimately, all those customers got their mail back, but it took up to three days to restore from tape backups (yes, tape!).

If Outlook.com starts acting up on you, here are two websites you should consult:

The Microsoft Hotmail, er, Outlook.com Service Status site (see Figure 4-3) gives you the latest information about Outlook.com's current health — from Microsoft's point of view. Unfortunately, in the past, the site has been criticized for being very slow to recognize reality. In the past few years, Microsoft's network going down has, at times, also taken the status reporting sites down, too (http://status.live.com/detail/hotmail).

downrightnow, which isn't aligned with Microsoft, gives you a crowd-sourced consensus view of what's really happening with Outlook.com/Hotmail. downrightnow (shown in Figure 4-4) not only actively solicits comments from people who visit the site but also has a Twitter monitoring program that finds some (not all) of the tweeted complaints in real time (www.downrightnow.com/hotmail).

Figure 4-3: Microsoft’s Outlook Service Status site gives a very broad overview of current Outlook.com status.

Figure 4-4: Compare the Microsoft Party Line with the crowd-sourced downright-now (which still calls Outlook.com “Windows Live Hotmail”).

Importing Outlook.com Messages into Gmail

If you find that you prefer Gmail to Outlook.com, you don't have to give up your @hotmail.com, @live.com, or @outlook.com e-mail address. Gmail gladly — I'm tempted to say "gleefully" — takes your Outlook.com mail, pulls it into Gmail and, if you reply to a message, tacks your @hotmail.com, @live.com, or @outlook.com address onto it. Your correspondents won't know that you've switched e-mail providers.

Assuming you have both a Gmail and an Outlook.com e-mail address, here’s how to set up Gmail so that you can read and respond to your Outlook.com mail via the Gmail interface:

1. Fire up Gmail and log in with your account.

2. In Gmail, tap or click the gear settings icon and choose Settings.

The Settings page appears, as shown in Figure 4-5.

3. At the top, tap or click Accounts and Import; then under the heading Check Mail from Other Accounts (Using POP3), tap or click Add a POP3 Mail Account You Own.

Gmail asks for the e-mail address.

Figure 4-5: The Gmail Settings page.

4. Type your @hotmail.com, @live.com, or @outlook.com e-mail address — the full address — and then tap or click Next Step.

Gmail fills in all the details for hooking into an Outlook.com (or Hotmail) account, as shown in Figure 4-6, and asks for your password.

Figure 4-6: Enter the details for your Outlook.com account here.

5. Type your password and then tap or click Add Account.

Gmail asks whether you want to be able to send e-mail using your @hotmail.com, @live.com, or @outlook.com address.

6. Choose Yes, I Want to Be Able to Send Mail and then tap or click Next Step.

7. Accept the rest of the default responses.

Gmail sends a message to your Outlook.com account to make sure you own it.

8. Tap or click the link in that e-mail message.

You’re all set up.

Gmail’s melding onto your Outlook.com account doesn’t change anything inside Outlook.com: You still get your mail in Outlook.com and can respond to it there, if you don’t want to use Gmail.

Questions about Outlook.com? Go to http://answers.microsoft.com.

Weighing the Alternatives

In Book IV, Chapter 2 I talk about choosing an e-mail program. Hotmail, er, Outlook.com is just one of many, many e-mail programs. At this moment, Microsoft offers about a dozen different e-mail programs:

The tiled, Windows 8.1 Metro Mail app (see Book IV, Chapter 2)

Outlook.com, formerly Hotmail (this chapter)

Outlook (many flavors in various versions of Office, some of them Exchange Server-based, some on Windows)

The Outlook Web App

The desktop program Windows Live Mail (see Book VI, Chapter 5)

The nearly identical twins Outlook Express (for Windows XP) and Windows Mail (for Vista and Windows 7)

With the exception of Outlook Express and Windows Mail, and to a lesser extent the various versions of Office Outlook, no two Microsoft e-mail programs look even vaguely similar. In particular, Outlook.com doesn’t look or act anything at all like Outlook.

Microsoft isn’t the only e-mail game in town, of course. Yahoo! Mail still has a lot of users, especially in the United States. Gmail’s in the same league, although its appeal reaches worldwide. Microsoft’s been trying to catch up with Gmail for years, and its latest switch to Outlook.com is widely viewed as an attempt to shore up Hotmail’s rapidly declining market share.

In Chapter 3 of this minibook, I cover Gmail in some depth and branch out to show you how Gmail, Google Drive, and Google Apps cooperate.

Outlook.com doesn’t tie in with the other Microsoft apps the same way Gmail ties in with Google Apps. Microsoft’s approach to an all-encompassing application solution, Office 365, uses Outlook and its variants for managing mail, not Outlook.com. (Confusing, yes, I know.) Although you can get your Outlook.com messages fed into Outlook, and you can coerce the Windows 8.1 tiled Metro Mail program to grab your Outlook.com messages, Outlook.com isn’t integrated into Microsoft’s Grand Scheme. Yet.