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Managing Your Life in the Clouds: A Guide for Windows Users, Part 3: The Yahoo! Experience

Part 3: The Yahoo! Experience

Like its younger but faster moving competitor Google, Yahoo! has always been a Web-oriented company, in this case one with humble roots, an auspicious boom era, and now what appears to be a long and steady decline. But Yahoo!'s been around for a long time, relatively speaking, and its experience and success on the Web shows: The company has purchased a number of hot online properties over the years and has done a reasonable job of integrating them into its stable of solutions. That said, Yahoo!'s offerings aren't as broad or deep as those of Microsoft or Google, and they're certainly not as well integrated. Yahoo!, is particularly lacking in the PC integration space compared to its competition. What Yahoo! has, of course, is a user base of hundreds of millions of customers. It's instant messaging (IM) platform runs neck and neck with Microsoft's, as does its online email system, and Yahoo!'s search engine, though a distant second to Google, routinely outperforms Microsoft's by a wide margin.

Put simply, Yahoo! may be running into a rough patch right now, but the company is popular enough to warrant consideration and powerful enough to weather the bad times if they execute correctly. Whether Yahoo!--independently or perhaps combined with other services like AOL--continues to be a player remains to be seen. But for now, they're just too big to ignore. Let's see what they've got.

Web solutions

Yahoo! offers a bewildering lineup of Web services, a fact that is hard to discover on its overly-busy Web portal. Most of them, of course, fall outside the boundaries of this discussion. But with only one exception, the relevant Web solutions listed here are woefully inadequate.

Email: Yahoo! Mail (free) and Yahoo! Mail Plus (,,

Contacts: Yahoo! Address Book

Calendar: Yahoo! Calendar

Photo management and sharing: Flickr (free), Flickr Pro

Online storage: n/a

Notes: Yahoo!' online services are deep but surprisingly poor once you examine them in any detail. Yahoo! Mail is a typical example: The service is in the midst of a long and painful upgrade to a new version, though the Yahoo! Mail Classic interface is still available for the Luddites. Skip that and look at the new version: It's by far the prettiest and most desktop-like of the Web-based email solutions. It's also the least mature: As you click around the interface, you'll see numerous apologies from Yahoo! as you're redirected to an older version of the site. And though Yahoo! Mail is free, it comes with serious limitations, especially if you're interested in accessing email from a PC or mobile device: There is no POP3 or IMAP support at all and no email forwarding. Yahoo! offers a paid Yahoo! Plus account for $19.99 a year, but even that is horribly limited: It provides POP3 access and email forwarding, and removes other limitations of the free version, but does not offer any IMAP access at all; I feel that IMAP is the baseline these days for email interoperability, because you can leave your mail in the cloud and then access the same database from anywhere, keeping things automatically synced up. Yahoo! Address Book is equally bad: Yahoo! currently offers two versions of the service, one that's integrated into the new Yahoo! Mail and one that isn't; the latter looks like the old Yahoo! services but displays the same data. Stupidly, different features are provided by each: In Yahoo! Mail Classic, you gain access to a free sync tool called Yahoo! Autosync (previously Intellisync for Yahoo!) that helps you sync your Yahoo!-based contacts between the Web and Microsoft Outlook Contacts and Outlook Express/Windows Address Book (and the Palm Desktop, increasingly useless), but it only works properly in Windows XP. (If you run it on Windows Vista, it will sync only to Outlook.) Yahoo! Calendar, likewise, is a mess. It's available only in the "Classic" UI style and can only be shared with other users, via the Web, who also have Yahoo! accounts. It's not compliant with Web calendaring standards, cannot be published to iCal, and cannot subscribe to iCal calendars. It is, in other words, almost completely worthless from an interoperability standpoint.

The one standout in this rogue's gallery of online garbage is Flickr, arguably the best online photo service currently available. Flickr is excellent for a number of reasons, but the best is interoperability: Thanks to its popularity online and a readily-accessible API, Flickr is supported by virtually every image application and online service on earth, and it is far more compatible with these applications and services than the photo management services from Microsoft and Google. The free version of Flickr provides up to 100 MB of photo uploads per month and a few other reasonable limits. Upgrade to Flickr Pro for $24.95 a year and you get unlimited storage, uploads, sets, and collections, no advertisements, and video uploads. Flickr is amazing.

Verdict: Yahoo! Mail would be attractive and usable if it was complete, but Yahoo! Address Book and Calendar look like they were last revamped in the 1990's. Flickr is the lone standout, and is a stunning example of what a successful Web service can and should be. That it originated outside of Yahoo! is, I'm sure, coincidental.

Desktop solutions

As a Web company, Yahoo!'s desktop offerings are predictably weak. The company is best known for its Yahoo! browser toolbar (which I find absolutely worthless, though it does provide Yahoo! Mail alerts) and IM client. Its Yahoo! Widgets utility is interesting if you're not already running Windows Vista, or have bought into the Yahoo! ecosystem and would like some integration pieces. (Yahoo! offers widgets for Contacts, Mail, Calendar, and Flickr.) Beyond that, there isn't much.

Email: n/a; unless you pay for Yahoo! Mail Plus, in which case you only get POP3 access; Yahoo! Toolbar provides Yahoo! Mail alerts

Contacts: n/a; can sync with Outlook and Outlook Express (XP only) if you know where to look

Calendar: n/a; can sync with Microsoft Outlook

Photo management and sharing: Flickr Uploader; integration with various third party applications including Microsoft's free Windows Live Photo Gallery

Notes: Yahoo! Mail desktop integration is notably weak: You can only access Yahoo! Mail from a standard email client if you purchase Yahoo! Mail Plus at about $20 a year. Or, you can use the Web interface and rely on Yahoo! utilities like its browser toolbar or Yahoo! Widgets to get email notifications. Yahoo! Address Book offers limited sync functionality via the aforementioned Yahoo! Autosync, which is badly in need of an update. Yahoo! Calendar is as non-interoperable as is Apple's MobileMe Calendar, and it's much uglier. (It is, however, free.) Flickr desktop integration occurs through a handy Flickr Uploadr tool, which works well. You can also use third-party applications to upload photos to Flickr; Windows Live Photo Gallery is an excellent choice. There are no photo editing facilities available to Flickr users, however, so you'll have to work with offline photos or utilize a growing collection of online editors that offer Flickr compatibility. My favorite is Picnik.

It's still in beta, but one other avenue of exploration for Yahoo! users on the desktop is Zimbra Desktop. This is essentially the Yahoo! Mail Web application bundled in a local Windows application frame and offering both IMAP and POP3 support to Yahoo! Mail, offline capabilities, and iCal support for Yahoo! Calendar. In other words, it offers pretty much everything that's normally missing from Yahoo!'s email and PIM services. Honestly, it's sort of a mess right now, so my advice here is that Zimbra could be of interest to those already using Yahoo!'s stuff, but it's not a good reason to jump ship to Yahoo!.

Verdict: Yahoo!'s desktop offering are uninspired, and until the company offers IMAP support to all Yahoo! Mail customers, I can't recommend using these products.

Mobile solutions

While Yahoo!'s desktop solutions are almost uniformly bad at the moment, its mobile solutions are surprisingly strong. Yahoo!'s mobile lineup includes native support for Yahoo! Mail on the iPhone and Blackberry, a growing suite of native mobile applications--the attractive Yahoo! Go 3.0 client (see a list of supported phones) and Yahoo! oneSearch currently, but more are on the way--and decent mobile versions of many of its online services, including Mail and Flickr.

Email: Native support on iPhone and Blackberry, via Yahoo! oneSearch on compatible devices, mobile Web access

Contacts: Native support on iPhone and Blackberry, via Yahoo! oneSearch on compatible devices, mobile Web access

Calendar: Yahoo! oneSearch on compatible devices, mobile Web access

Photo management and sharing: Native Yahoo! Flickr on compatible devices, Flickr for Blackberry, mobile Web access

Notes: While your results will vary wildly depending on which mobile device you're using, Yahoo! offers fairly comprehensive access to its Web services via a growing army of devices. Its native Yahoo! oneSearch and other applications look excellent, and the company is quickly developing new mobile applications as well. Native support for Yahoo! Mail on iPhone and Blackberry is excellent.

Verdict: Yahoo's mobile support is as good as it can be, given the wide range of devices the company is trying to support.

Final thoughts

Yahoo! represents an interesting dilemma to potential users, as its Web services seem to be falling a bit behind the curve, while most of its desktop solutions are almost laughably bad. Where the company shines, confusingly, is in the mobile space, though of course your results could vary depending on your device type. At this time, Yahoo! doesn't appear to offer the same seamless experience that both Microsoft and Google do, but I will say this: If you're interested in a true cloud computing experience, where all of your desktop interaction with the system will actually occur via the browser, Yahoo!'s solutions aren't so horrible. The key here is interoperability: No, Yahoo!'s calendar solution doesn't offer industry standard iCal support (outside of Zimbra) but it does work fine via the Web and integrate with the company's native mobile applications and mobile Web apps. If getting this data onto the desktop isn't a huge concern, Yahoo! could fit the bill. But I still feel that this is something that only existing Yahoo! users should investigate. Those looking in from the outside would be better off with other solutions for the most part. The sole exception, of course, is Flickr. But then, that's where the next part of this overview comes in. The nice thing about these solutions, of course, is that you don't have to stick within one environment. Instead, you can mix and match, and pick the services that make the most sense for your particular needs. And that's exactly where this whole thing is going to wrap up.

Next: Putting it all together ...

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