Coping with Windows Live Hotmail Wave 4

Woody leonhard By Woody Leonhard

Microsoft’s new version of Windows Live Hotmail brings several new features to the online-mail table.

Some of you have written me with tales of woe, cursing the new version and the Windows Live horse it rode in on and begging to get your old Hotmail back. Sorry, you can’t.

All is not doom and gloom. As you’ll see, the new Wave 4 Hotmail does have its redeeming social values. And if you’re still suffering through the changes, there are a few tricks that might make dealing with the newer, shinier version easier.

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Hotmail has had a long and bumpy history. Fifteen years ago, Sabeer Bhatia and Jack Smith left Apple Computer and started a free e-mail service known as HoTMaiL. A year later, with more than a million customers in tow, Microsoft bought the company and renamed the product MSN Hotmail. Hotmail went through a dozen significant changes in the course of several years, with each incarnation promoted as making it “just like Outlook.” Of course, Hotmail isn’t anything like Outlook — not then, not now.

MSN Hotmail also suffered a couple of short-lived name changes, confusing everybody, but ultimately emerged as Windows Live Hotmail in 2009. Wave 4 might be a catchy moniker for Version 4, but it raises the embarrassing question of what happened to versions 1 through 3. I figure Hotmail’s up to version 100+. The various Windows Live components aren’t quite as long in the tooth, but some of them have been through dozens of changes, too. When I ask developers what they think Wave 4 means, the invariable response is, “Go ask marketing.”

Microsoft’s fighting for online eyeballs and a slick Hotmail helps. The numbers vary wildly, but a couple of months ago, one source put Hotmail’s share at around 20%. Yahoo’s Mail was north of 50% (counting visits to the Web site), Gmail came in at around 12%, and AOL Mail was at about 8%. However, a recent Wall Street Journal article (fee-based content) reports that Yahoo’s e-mail business just took a swan dive.

The stats don’t really matter. What’s important is that a huge number of Hotmail subscribers are facing potential problems as they are moved to Wave 4.

In my July 22 Top Story, “Windows Live shares your Messenger contacts,” I talked about privacy problems with beta versions of Hotmail and other recently updated Windows Live apps. Those problems still exist, but many of you will continue to use Hotmail anyway. I do — though I find myself using Gmail more, and better privacy is the reason why.

New features make attachments easier than ever

Wave 4 adds several useful new features to Hotmail. Many of them — such as the new built-in media viewers — don’t require any retraining on the part of Hotmail users. You can, for example, watch linked YouTube videos inside an e-mail message. Integrated Office Web apps support lets you work with Office documents within Hotmail — albeit in a limited Web-apps way.

SkyDrive integration works with little effort if you click on the correct button. (Michael Lasky’s June 24 Top Story steps you through the details on SkyDrive.) With SkyDrive, Hotmail lets you attach and send as many as an astounding 200 photos (each up to 50 MB) in a single message. You do so with these steps:

Create a new message, click Photos, and then click Create album on SkyDrive. Next, select the images you want to upload. Hotmail automatically uploads the files to SkyDrive (this can take some time, depending on the number and size of the photos) and creates thumbnails in your message. Status bars next to each thumbnail give its upload progress. (Note: you’ll have to install Microsoft’s Silverlight to upload the files to SkyDrive.)

The e-mail recipient has the options of admiring your thumbnails, clicking through to SkyDrive to view the originals as a slide show, or downloading the original files as a zip.

This new method has a couple of important advantages. It makes the size of e-mails containing photographs much smaller, and that saves time when the recipient opens the message. It also solves a Hotmail storage problem: in the old Hotmail, those monster image files lived forever in your Sent folder, soaking up storage space — unless you remembered to delete them. With Wave 4 Hotmail, image albums automatically disappear from SkyDrive after a month.

A warning: If you’ve ever e-mailed a bunch of pictures to yourself, expecting you could retrieve them some months later, you’re now out of luck. You can increase the expiration date on the album by clicking the link Edit album details, which appears in the upper-right corner of the Hotmail new message screen. SkyDrive lets you increase the expiration time to 90 days, or you can choose to store them permanently. There’s no way to change the default setting for all of your future albums — if you want your pictures to stick around for more than 30 days, you need to manually change the expiration date.

Take control of your inbox — carefully

If you’ve ever fussed with Outlook’s rules, you’ll immediately understand the appeal of Hotmail’s new Sweep function. You can automatically move all messages sent from a specific e-mail address into a special folder — one you created or the Junk folder. Here’s how:
  • Step 1. Start in your Inbox. If you want to move all the messages into a folder that you set up, hover your mouse over the Folders link on the left, click on the small wheel icon, choose Add a new folder, and give your new folder a name.

  • Step 2. Back in your Inbox, click on a message that comes from the e-mail address you wish to banish — er, sweep.

  • Step 3. In the toolbar at the top of the Hotmail screen, click Sweep and then Move all from. Choose the folder you want to move the messages to and click Move all. If you want to set up a permanent Sweep rule, check the box marked Also move future messages.
If you’re a more trusting soul than I am, you can use Hotmail to manage your Gmail, Yahoo Mail Plus, or other POP3-based e-mail accounts — up to a maximum of four accounts. (Yahoo Mail Plus is a paid account service.) When you send a new message, you can choose which account appears in the From account box, although it will appear in a format like “From on behalf of” — not exactly elegant.

(For information on managing multiple e-mail accounts in Outlook, see Lincoln Spector’s companion piece, “Managing multiple e-mail accounts in Outlook,” in the paid section of the newsletter.)

Hotmail now has a Conversation view — it groups messages by subject-line text instead of by chronological order. To flip into Conversation view, click on Inbox, Arrange by (upper-right corner of the Inbox), then Conversation.

Coping with the inevitable Hotmail gotchas

It would seem that Microsoft believes it has eliminated the major reported Hotmail Wave 4 problems. In a Hotmail forum, a moderator-locked Aug. 10 thread lists a few Hotmail issues and some workarounds.

If you look at the forum’s home page, a few hundred posters are still sounding out — some vehemently — about problems with Wave 4. Microsoft’s responses tend to follow a prescribed pattern. (I won’t say they have a bunch of canned responses, but many of them look, uh, amazingly similar.) If you’re experiencing a problem with the new Hotmail, check out the forum for any useful Microsoft advice and post a question if none of the answers fits your difficulties.

One final tip: After upgrading to Wave 4, some Hotmail users discover they can no longer get into their accounts (can’t log on, can’t read mail, or can’t send mail) by going to A few can get into Hotmail by using Windows Live Mail, the heir to Outlook Express in Windows XP and Windows Mail in Vista. If you’re at your wits’ end and can’t get Hotmail to budge, follow the steps posted by Technogran (yes, that’s a contraction of “Techno” and “granny”) on her blog. It’s easy, and some people say it even works!

Have more info on this subject? Post your tip in the WS Columns forum.

Woody Leonhard‘s latest books — Windows 7 All-In-One For Dummies and Green Home Computing For Dummies — deliver the straight story in a way that won’t put you to sleep.

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All Windows Secrets articles posted on 2010-09-16:

Woody Leonhard

About Woody Leonhard

Woody Leonhard is a Windows Secrets senior editor and a senior contributing editor at InfoWorld. His latest book, the comprehensive 1,080-page Windows 8 All-In-One For Dummies, delves into all the Win8 nooks and crannies. His many writings tell it like it is — whether Microsoft likes it or not.