One welcome sign is an effort by companies trying to improve Microsoft Corp.’s (MSFT) Windows Mobile operating system, which has a reputation for confusing navigation and hasn’t had a major update recently. Kinoma Inc., for example, recently released an application called Kinoma Play that runs on Windows Mobile devices and gives users a markedly better way of handling photos, videos, music and Web browsing.

The HTC Touch Diamond, due out this month from Sprint, tries to hide Windows Mobile software.

This week, I tried yet another software program that is designed to run on top of Windows Mobile software. But this time, the software is at the heart of a device designed by the same company: HTC Inc. I tested the HTC Touch Diamond, due out from Sprint (S) sometime this month for $250 (after a $100 mail-in rebate) with a two-year contract.

Taiwan-based HTC started out in 1998 as a maker and designer of mobile devices for other companies. A year ago, HTC launched the first device under its own name in the U.S., and now, Sprint, AT&T (T) and T-Mobile (DT) sell HTC-branded devices. The Diamond incorporates HTC software, as well as software from Sprint, MobiTV, TeleNav and others. But it isn’t a stretch to imagine HTC trying to create a fully end-to-end model (hardware and all software) in the future.

The Diamond has a touch screen, but it’s smaller than Apple’s (AAPL) iPhone — 2.8 versus 3.5 inches. This screen lacks the iPhone’s multitouch functionality, and its smaller size robs space used for touch gestures like flicking or scrolling with a finger. Yet like the iPhone, it relies solely on an on-screen keyboard for all text entries. Even with the Diamond’s stylus, the keyboard felt small and cramped. Using just your fingertips was next to impossible.

After using the Diamond for a week, I can say that despite its handsome TouchFLO 3D software and animated icons like photos that flip from one to the next with a flick of finger, this device failed to disguise the frustrating interface of Windows Mobile often enough for my taste.

It reminded me of the brown paper bag book covers my Dad helped me make for schoolbooks when I was a kid: They looked great on the outside, felt sturdy and clean and created a blank canvas for homemade doodles that were often more interesting to me than the books they covered. But my book covers couldn’t change what was underneath; pages of frustrating algebra were just a flip away.

HTC’s sleek software tries to hide Windows Mobile, but menus from the Microsoft operating system are constantly popping up. HTC’s email program, for example, is represented by an animated envelope icon that, when selected, cleverly flips twice before sliding an email message half-way out and giving you a three-line peek at what’s inside. If only reading and responding to email were half as entertaining. Selecting the animated envelope opens the old, cumbersome Windows Mobile email program.

Also, the touch capabilities of the Diamond’s screen didn’t work as well as they should. Finger flicks that should have scrolled through lists instead seemed to select individual items in a list, as if they were sticky.

The Diamond isn’t all bad, of course. Plenty of people will like its smaller size because the iPhone and RIM’s (RIM) BlackBerrys seem too large and brick-like to hold up to an ear for phone calls. Next to my BlackBerry Curve, the Diamond was of comparable thickness but measured smaller in width and length.

Despite its size, the Diamond is packed with features. It has a 3.2-megapixel camera with autofocus that doubles as a camcorder, and comes with four gigabytes of internal memory and a removable battery. I taped short videos — something the iPhone can’t do — and found the sound and video footage to be adequate.

HTC touts the Diamond’s browser, which is based on the Opera browsing engine but is designed for HTC. It opens Web pages in views that fit the screen and text is automatically resized as users zoom in or out, though this resizing was sometimes slow.

Unlike the iPhone, Web sites that are opened on the Diamond’s browser don’t resemble the actual site as you would see it on your computer. I opened CNN.com (TWX) and WSJ.com (NWS), two sites that are packed with text and graphics on a regular browser. On the Diamond, they quickly were rendered in list format with mostly text-only. I easily touched the screen to follow links to full stories.

Like the iPhone, the Diamond has an accelerometer, though it’s called the “G-Sensor.” When it worked, this feature flipped the screen to match the horizontal or vertical direction in which the device was being held. Photos flipped instantly, but the Diamond’s G-Sensor took almost three full seconds to respond as I flipped from vertical to horizontal while using the browser. And some Web sites didn’t respond to the G-Sensor flips at all.

A special YouTube application developed by HTC was easy to find on the device and worked quickly. My videos were organized into categories for All, History, Bookmarks and Search, though this last category required using the finger-fumbling keyboard. In one step, I emailed a link from a YouTube video to a friend using the device, with a still shot from the video included in the message.

Overall navigation on the Diamond isn’t as intuitive as on the iPhone or iPod Touch, nor was it as easy as on a touch-screen Windows Mobile device running the Kinoma Play application. The iPhone and iPod Touch use quick double-taps on touch screens to zoom in or out, and multitouch capabilities resize images with pinching gestures; Kinoma Play uses a long touch to zoom in. The Diamond used double tapping on some screens, but not enough for me to grow comfortably reliant on it. A small, circular pad beneath the device’s touch screen provided a more dependable method for zooming in or out of screens: tracing the perimeter of this circle clockwise with a finger zoomed in; counterclockwise zoomed out.

The HTC’s software animation is put to good use on its Weather screen. Here, animated illustrations of each day’s weather appear on the screen: suns spin, clouds move in, rain appears to fall. Even moons appear on the device at night to accurately reflect the weather in a city at a specific time.

It is exciting to think about other mobile-phone companies giving better software a real try, especially those that attempt to improve Windows Mobile. But HTC’s Touch Diamond doesn’t hide the outdated operating system well enough or often enough for a user to want to buy a whole new mobile device.

Edited by Walter S. Mossberg

• Email us at mossbergsolution@wsj.com. Find this and other columns and videos online free at the All Things Digital Web site: http://walt.allthingsd.com

This week, I tested two free Web sites that don’t try to steal users away from their trusted travel Web sites. Instead, these sites attempt to make your already booked reservations more useful and accessible.

I tested two such sites: TripIt Inc.’s www.TripIt.com, which acts as a virtual assistant to generate schedules using your reservations; and Groopvine (http://Groopvine.Groople.com), a feature offered by Groople, Englewood, Colo., that brings social networking to group travel plans. Both travel aids became available in September, though Groopvine has been released only in its beta, or testing, stage.

As someone who makes travel arrangements for about 10 work-related or personal trips every month, I paid close attention to the simplicity and usefulness of these sites. TripIt’s straightforward approach makes it addictive: When I forwarded travel confirmation emails to plans@tripit.com, the information in each reservation was automatically assessed, compiled and organized into a schedule, which was emailed to me in seconds.

Groople (a mashing of the words “Groups” and “People”) started four years ago as a site that helped big groups book hotels, flights and other travel arrangements. Groople’s new Groopvine tool offers group booking, but it focuses on working as an online forum where trips can be discussed among those in the traveling group. Photos, polls, videos and Web feeds can be added to each group’s trip page, prompting everyone to participate in the trip planning — or at least get excited about it.

I found a few hiccups on both sites. TripIt duplicates plans on a schedule if you accidentally forward a confirmation email more than once, and it works with most but not all reservations. Groopvine’s trip pages are rough around the edges in some places, obscuring key features and making certain flight and hotel ideas impossible to share with the group. But each site is helpful in its own way.

TripIt is a refreshing switch from the Web sites that force people to create usernames and passwords before doing anything. I started using TripIt by forwarding an Expedia email reservation to plans@tripit.com. Less than a minute later, I received an email from TripIt that included a link to my itinerary of flights, local weather forecasts for the duration of my vacation and maps related to where I was going. This email also included an assigned account ID (the email address from which I forwarded the reservation) and a password that I easily changed from within the account’s Web settings.

Along with this first test from Expedia, I forwarded a variety of other reservations to TripIt including bookings for a hotel in Atlanta, a rental car in Washington, D.C., and a round-trip Amtrak train from D.C. to Wilmington. I forwarded the reservations from various email addresses (as long as they were listed in my account), and each reservation was added to the right itinerary according to date.

TripIt can also accept forwarded restaurant reservations made on OpenTable or TopTable and will sort these into the itinerary.

This Web site’s idea of asking users to do very little to get a fully organized schedule works well, though everything can be edited. I unknowingly forwarded the same car rental to plans@tripit.com twice and two car reservations appeared on my itinerary, making me think I booked two cars until I saw the confirmation number repeated and deleted one. Attractive pre-loaded icons or your own photos can be added to the top of each schedule, as well as other plans for while you’re traveling, including images and Web links.

A feature called TripIt To Me lets you retrieve anything loaded into TripIt by simply emailing a command to the site, such as “Get Flight Tomorrow.” This worked well on my BlackBerry.

I started using Groopvine by signing up and creating a trip page for an annual vacation. I walked through steps to create my page, which I titled and set to a certain color scheme. I chose pink hues and added various sections to my page for displaying polls (to get votes from invited travelers), photos, videos, RSS feeds (for news related to the trip destination, for instance), weather, group discussions and useful Web sites.

I invited a group of friends to join my trip, and everyone accessed the trip page without needing to first become a member of Groopvine. Instead, usernames and passwords are automatically created for return sign-ins. In a few short steps, I made one poll asking friends where they thought we should go and another to ask them how many days they preferred to spend on vacation.

My fellow travelers and I added photos to the page that showed up in handsome Web 2.0 fashion, popping out from the screen in a box overlaid on the page at the click of a button. But I was disappointed that more of the site didn’t take advantage of this technology, which saves users from jumping to new Web pages. While browsing hotels and flights — two important parts of travel arrangements — I was directed to sites away from my personalized trip page.

Users can share hotel suggestions with the group by selecting up to five at once and asking others which they prefer, including details like room rates and amenities. When starting a trip, you must choose from a list to tell Groopvine what the trip is for (i.e. class reunion, sports team travel, family vacations, etc.). From that information, Groopvine suggests certain hotels depending on your group. A school trip, for example, would automatically return results with hotels rather than motels because motels don’t keep kids as contained and safe.

But in a search for Arizona hotels, I couldn’t share any of my choices with the group without first booking rooms. Groople says 70% of its hotels are shareable before booking, so I guess I picked the wrong city. I looked at flights and fares from various airlines, but (again) couldn’t share my findings with the group unless I booked a trip first or knew specific details about flight options. Groople says sharing flight information before booking — as is done with hotels — isn’t possible yet, though the company is working on finding a way to do it.

I’d prefer to share flight options with my group as I came across them. But it’s understandable that flights are difficult to share because fares change so often and various seats and fares are offered to members with different airline statuses. Another challenge with airlines is that only six reservations can be booked online at a time. Groople Agents, reachable by phone, can assist with challenges like these at no charge.

On March 11, Groople plans improvements for Groopvine, including fixing the hotels so that all of them are searchable and sharable. A new opt-in feature will automatically notify each traveler via email of changes on the trip site.

If you wish you had a personal assistant to arrange your travel reservations into a neat itinerary, TripIt does a great job and requires minimal effort and time. Its itineraries look polished, combining reservations into one neat list per trip that can be retrieved at any time. Groople’s Groopvine will encourage groups to get excited about their coming trip, whether they booked it through another favorite travel Web site or through Groopvine, itself. Hopefully, the impending fixes due in March will make this site’s pages more user-friendly.

• Email mossbergsolution@wsj.com.

Owners of the $399 iPhone can get a free update, but those with the $299 (8 gigabyte) or $399 (16 gigabyte) iPod touch must pay $20 for their update because Apple tracks revenues differently for iPhones compared with its iPods.

Updates for the iPhone and iPod touch add Web bookmarks to the home screen and a redesigned Maps application that displays a user’s current location.

This week, I’ve been using an iPhone and iPod touch with these updates, and I must say that both devices are much more useful and fun with these improvements. Web clips, or browser bookmarks that take the form of icons on the home screen, give these gadgets a new sense of instant gratification because they direct users to specific Web pages seconds after the device turns on. These little icons can be labeled and moved around, letting you group favorite Web sites on one screen, games on another screen, saved Web research on a third screen and so on.

Getting Synched

Both devices can be updated by synching with iTunes; the iPhone does so automatically and the iPod touch updates only if the owner buys this upgrade through the iTunes Store. New iPod touches include the updated software free.

New to both devices is a redesigned Maps application that, at the touch of a button, displays a user’s current location in an on-screen map — without using Global Positioning Systems. Other non-GPS devices currently do this, but they depend solely on cellphone towers to determine your spot. The iPhone uses both cellphone towers and nearby Wi-Fi hot spots to find your location; the touch uses only the Wi-Fi method.

The iPod touch also now has the same stellar Mail program that is found in the iPhone, a real plus for owners who have been curious about mobile email but weren’t necessarily ready to plunge into a BlackBerry or iPhone, or don’t want to pay for a monthly data plan.

Both devices can store numerous Web clips on up to nine different home screens, each of which has room for 16 icons. A handful of permanent applications appear by default on the main home screen, but these can be shuffled around. Along with Maps and Mail, applications for Stocks, Weather and Notes were also added to the iPod touch.

Multi-touch technology only improves these new features. For example, home screens are easily navigated by flicking a finger horizontally to get from one to the next. Holding a finger on any Web clip causes all of them to jiggle like tiny pieces of digital Jell-O, waiting for you to either delete or drag them around wherever you would like them to stay. Pressing the Home key cements the icons in place.

Trouble Finding Home

But these updates left room for improvement. Maps had trouble on both my iPod touch and iPhone when I asked it to find me in my home in Washington, D.C., and in my office near the White House — the former test circled a 30-block radius while the latter marked me four blocks away. Tests in other locations worked well, and clever “Drop Pin” tools helped me mark and label specific places. But I wouldn’t rely on this feature if I was completely lost and hoping the iPhone or iPod would tell me where I was.

And though I was excited to have email on my iPod touch, this device lacks a speaker and vibrating capabilities, so it can’t chime or buzz to signal newly received email. Because of this, the touch wouldn’t work for me as a serious, everyday tool like the BlackBerry and iPhone.

The free update for the iPhone lets you text message multiple people simultaneously, something the most basic cellphones have been doing for years. But individual responses to these mass texts can’t be seen in the same thread of conversation as that which you started; instead, they generate new text message threads.

On the iPhone and iPod touch, the Maps application now shows hybrid views that combine satellite maps with labeled street names, which are helpful.

The iPod touch is a testament to what can be done on a mobile device without a cellphone carrier’s help. By tapping into Wi-Fi hot spots, which are almost everywhere, I easily checked email, stocks and weather. I had a little more trouble using the Maps application with Wi-Fi because I was more often checking my location while on-the-go in a car or walking.

Collecting Web Clips

I had fun populating the many screens of my iPod touch and iPhone with new Web clips. These are easily added by hitting a “+” symbol at the bottom of any Web page, naming the Web clip and watching it appear on a home screen, often with a colorful accompanying icon like that for AllThingsD.com.

Snapshots of a Web page can be captured and saved in a Web clip by zooming in on a certain section of a page and saving that specific view. This proved helpful when I needed to quickly glance at the Georgetown basketball schedule a few times in one day.

Web applications can be found at www.apple.com/webapps. A game called Ditto involves repeating a pattern on blue, yellow, red and green squares using the touch screen — a digital version of the Simon handheld game. Memory, the old card game, is updated with animated animals on cards. FlyTunes lets users listen to customizable channels from Internet radio, while an app called Floort presents an opinionated topic and asks people to vote on whether they agree or disagree. Even simple Web apps were useful, such as one that turns the screen into a virtual ruler with inches on one side and centimeters on the other.

But it’s good to keep in mind that these are Web applications, and are useless without the Web and/or an AT&T connection.

All in all, Apple’s software updates for the iPhone and iPod touch are exciting, especially because they make home screens much more useful and individualistic. These tiny devices continue to become truly mobile computers.

• Email mossbergsolution@wsj.com.