Before Microsoft launched Windows Phone 7 in 2010, they had a smartphone operating system called Windows Mobile which was based on a version of Windows called Windows Compact Edition. It was extremely flexible and feature rich. More so than Android and iOS at the time and in some ways even more than those operating systems today. People hated it because it was too complicated and too difficult to use even though ironically it was much easier to understand than today’s Android and iOS user-interfaces that are so popular. A decade ago, Windows Mobile was basically the king of mobile device functionality. With Windows Phone 7, Microsoft changed directions and went with something very simple and beautifully designed, which is what so many iPhone users thought we as consumers wanted. It turns out actually we wanted lots of flexibility and functionality instead, so Android picked up that slack and became king of smartphones. So today, whenever we see some great new feature from Android or iOS or even Microsoft, it was often already possible in Windows Mobile around the turn of the century.


Continuum is one of the big Windows 10 Mobile features that allows you to plug your phone into a bigger screen along with a full-sized keyboard and mouse in order to use the apps on your phone in a more-PC-like environment (rather than having to suffer through the touch screen keyboard.) Classic Windows Mobile had something like this in 2008. The Redfly Mobile Companion was a 3rd party piece of hardware that did essentially the same kind of thing that Microsoft’s new Continuum feature is going to do except with a more-portable laptop-like piece of hardware.

SMS and Phone Dialing from the PC

JeyoMobileCompanion_Inbox-21Back in the days of the Windows CE version of Windows Mobile pre-2010, one of my favorite features was being able to type text messages and initiate phone calls while my phone was plugged into my PC and charging. Software like Jeyo Mobile Companion and SOTI Pocket Controller made this very easy. Now there are plenty of indications that this capability will be coming back to Windows Mobile 10. That’s good news because 10 years ago, being able to use a real full-sized keyboard to type out SMS messages was so excellent. With Jeyo Mobile Companion we could also save and back-up SMS conversations as XML files and reference them on the desktop. Hopefully we’ll see something like that return in Windows 10 Mobile, too.

Digital Inking support

Before Steve Jobs came along and said, “If you see a stylus, they blew it.” the whole handwriting recognition on smartphones was pretty advanced. After the iPhone came along, these stylus interfaces became extinct for quite a while. Although, now we’re seeing a resurgence beginning with the Samsung Galaxy S Note. Anyway, Classic Windows Mobile had digital inking support throughout the operating system. In the early “Pocket PC” versions, the digital ink was even more pervasive. You could use a stylus to draw or write whatever you wanted in ANY notes field. Even email messages supported the digital ink. The drawings would sync right into Outlook on your desktop too no matter if you were drawing in an appointment’s notes field, a contacts note field, or the actual Outlook notes. In fields or apps that didn’t support digital ink directly, you could easily switch to the handwriting recognition or character recognition software input panels to write out words with ease and speed.

Today we hear rumors that Microsoft is working on bringing stylus and handwriting recognition support back to Windows 10 Mobile. It makes a lot of sense since the Surface Pro stylus has been becoming pretty popular and has grown some excellent new functionality with the Surface Pro 4. Unfortunately since Microsoft has had to start-over a few times between Windows Phone versions, all the progress made with the classic Windows Mobile has been lost. The system-wide type of digital inking support we saw with Pocket PC 200x may not return in the same form, but hopefully we’ll see a good implementation in the future.

Keyboard shortcuts

If you know about working efficiently, you know about keyboard shortcuts. Windows Mobile classic and Windows CE always had support for this if you connected an external keyboard or had one built in. Yes, they’re coming back in Windows 10 Mobile! Even Ctrl + Z will work for “Undo”, and the support for wireless Bluetooth keyboards was already added back in a recent version of Windows Phone 8.1. Hopefully someday we’ll also see the same keyboard mnemonics that have been standard in Windows on the desktop for decades (and also used to be in Windows Mobile classic). Unfortunately, currently Windows 10 Mobile and even Windows 10 universal apps do not have keyboard mnemonics that would have made keyboard navigation much easier.

Instant switching between input panels

Back in the late 90’s, the PDAs that would eventually evolve into smartphones often had difficult-to-learn text input methods. The popular Palm Pilots had a hardware panel where you would write gestures to create letters, but you had to learn this completely new language of writing letters called “Graffiti”. Windows CE, Pocket PC, and Windows Mobile (classic) had screen-based input panels at the bottom of the touch screen just like all smartphones do these days, but what was extremely awesome about this was that you could install 3rd party input panels and switch between them with a little pop-up menu at the bottom even in the middle of typing.

With devices like the HTC Touch Diamond which had sensors for the stylus silo, I even had my input panel automatically change from finger-friendly T9 style keyboard to a stylus-friendly digital ink character recognition panel as soon as I removed the stylus from the phone! That was extremely convenient!

Today, Apple’s iOS and Google’s Android now support installing third party input panels and software keyboards, but in order to switch between them, you have to go dig into the settings section and choose it there. There’s no on-the-fly swapping anymore, and of course Windows Phone removed this capability in order to make things more-simple like all the iPhone users thought they wanted back in 2010.

System-wide themes


One of my favorite things in Windows desktop operating systems of old was the system wide theme customizations. If you decided everything should have purple accent colors, that was very easy to do and all of your programs would pick up the colors you chose. It made everything feel cohesive and consistent even if some of your programs were made by third parties. Windows Mobile classic implemented the same type of thing. No matter what program you installed, your chosen colors were going to be part of the title bars, menu bars, etc. (Although the media player and phone dialer required different themes to be built separately.) Pocket PC themes were so popular, we actually had a huge primary section at dedicated to sharing custom made themes many years ago.

Windows Phone and Windows 10 Mobile still have that system wide theme option, but app developers tend to ignore it. Everyone wants their bit of software to have its own goofy “branding” that clashes with the rest of the system. Microsoft itself fails spectacularly when it comes to this global cohesive design among its own apps. In the Windows 10 Mobile start screen, ideally all of my live tiles would have transparent backgrounds that showed my chosen image and colors so that my layout would look really great. Unfortunately, apps like Skype, OneNote, Word, PowerPoint, Excel, Microsoft Health, Xbox, Xbox SmartGlass, MSN Weather, MSN News, Lumia Camera, etc. all give themselves different colors that look terrible on the start screen. They take their own color schemes into the apps too, which again looks horrible and inconsistent.

It’s like having every wall inside your house designed by a different person. Maybe this wall is all purple, but this wall is black with orange accents, and this wall is white with light blue cloud shapes on it. Horrible! At least Outlook Mail & Calendar on Windows 10 Mobile have implemented their own color options which allows you to choose the system theme as the apps’ theme.

Real Personal Information Management

Windows Mobile had really useful PIM management software at the turn of the century.
Windows Mobile had really useful PIM management software at the turn of the century.

These days everything generally follows the lead of the old Exchange email servers where, in addition to your email, you’d get your contacts, calendars, and tasks syncing with the server over the internet. 15 years ago, our PDAs and Smartphones were made to sync with your personal information management software located on your PC (usually Microsoft Outlook). Maybe that software also synced with an Exchange server, but maybe it didn’t. At any rate, somewhere along the way the smartphone mobile versions of Outlook lost a lot of functionality. That trend continues with Windows 10 as it no longer supports syncing task lists from Exchange. That means if you are assigned a task in Office 365 or you’ve created your own, you won’t be reminded when they’re due. Windows 10 mobile doesn’t even sync email drafts on the server, nor does it sync reply/forward status indicators with any kind of email server. Meanwhile, Exchange/Office 365 have added new features over the years and the mobile clients have not kept up at all (especially on Microsoft’s Windows 10 platforms). Mobile clients don’t even support PIM features that have been around for decades. You still can’t edit server side rules or even access shared/public Exchange folders.

Data syncing with Outlook and Exchange was far more powerful back in the classic days of Windows Mobile. Exchange Notes used to synchronize too, and with a third party app called JournalSync, even Journal entries could sync to your phone. There was even a “new note” button in the phone dialer that would automatically populate the note with your phone call’s info giving you instant access to writing info down while speaking to someone. If you’re a pro at efficiently organizing your stuff in Outlook, you’re probably using categories and rules for everything. Windows Mobile used to be able to actually sort your contacts by assigned categories making it easy to find a whole group of people you want to contact, but that feature is nowhere to be found ever since Windows Phone 7 hit the reset button. It could also sort contacts by company and even display contacts that were not assigned a category yet. Organizing and managing personal information has since become much less robust not only on Windows 10 Mobile, but on all smartphone platforms.

Dual Booting

Back in the early days of Android, Windows Mobile was the king of customizable smartphone operating systems. Some of the UI replacements on Windows Mobile were far more comprehensive and unique than anything we’ve seen on Android. Still, one of the coolest things about having a Windows Mobile device like the old HTC HD2 was the ability to dual boot. That device was hacked to run just about any ARM compatible operating system of the time. Feel like using Android? Just select the option and reboot. We’ve heard this kind of thing might be coming to some Windows 10 Mobile devices, too.

A useful speech interface

My phone actually spoke useful information out loud in 2005.
My phone used to speak useful information out loud.

In 2003, Microsoft had the best speech interface on a smartphone. Microsoft Voice Command enabled a whole slew of things you could do without touching your phone or looking at the screen. That’s the whole point of a speech interface; hands & eyes free usability. I could have incoming text messages automatically read out loud and reply to them using whatever microphone was connected. I could hear the name of whomever was calling read out loud. I could ask about my schedule or tell it to play certain types of music. I could even ask it for help by saying “What can I say?” and have a whole conversation about learning the commands that it recognizes. I could ask about the battery level, the time, I could tell it to shut off Bluetooth or go into airplane mode. All of this at a time when Apple was making portable hard drives with headphones that played MP3s and displayed the song title on a tiny black & white screen. The best feature was being able to read aloud appointment reminders. If my phone was on the charger or in my jacket while riding the motorcycle, it would speak into my ear, “Appointment in 15 minutes, Drive to Dinner” and I would instantly know what I was supposed to do next. No need to look at my phone’s screen, pick up the device, or even look at my wrist.

Then with Windows Phone 7, all of that was lost, but we saw some hope of it coming back in 7.5 when in addition to the hands-free text-messaging speech interface, Windows Phone could also instantly read aloud Windows Messenger and Facebook Messenger instant messages! You could actually have full Facebook chat conversations while driving without looking at or touching your phone. All of that was again lost in later versions of Windows Phone and now we’re stuck with something that is only capable of communicating with unintelligible sound effects that make zero sense.

One handed-usability

OldPhone_WP_20140806_09_13_53Smartphones originally evolved from combining PDAs and cell phones in order to create a single tool for getting things done on the go. That was great. You could reply to an email, check your text messages, load up the weather, and edit a Word document while carrying your luggage at the airport. Windows Mobile Smartphone Edition put all functions within reach of tactile hardware buttons that you could feel and activate without looking. Since the iPhone showed up, smartphones have evolved into large touch screen toys who’s primary functions are no longer mobile productivity, but rather entertainment and generating “likes” on social networks.

Those operating systems that have implemented a one-handed-usability mode, have done so in a way that’s pretty insulting to a mobile power user’s intelligence. Instead of simply designing the entire interface to have buttons that are within reach of the user’s fingers, iOS, Android, and Windows 10 Mobile require you to activate some silly shortcut mode that moves the top part of the screen towards the bottom so that you can reach the buttons. This makes half the screen unusable and requires extra effort that slows you down significantly and is almost as frustrating as having to use two hands.

Compare this to classic Windows Mobile devices who had hardware buttons at the bottom (or on the sides with scroll wheels) that let you control the entire device with minimal finger movement. Many devices even had customizable hardware buttons. This was essential to increasing your mobile efficiency. I could set one button to switch to the GPS navigation program, another to switch to the MP3 player, another to activate voice command listening, others to control the music. It was much easier, faster, and safer to use.


As mentioned in the beginning, Microsoft trashed all of the great stuff they had done with their mobile operating systems for the previous decade in 2010 and started over with Windows Phone 7, which actually introduced a lot of really great features. The hubs and panoramic designs were gorgeous and innovative ways of reorganizing the mobile operating system interface into something that made a lot of sense. Most of that was rebuilt when they started over again with Windows Phone 8 built on the Windows 8 kernel, and then just about all of that was trashed again when they started over with Windows 10 Mobile which is meant to unify the mobile operating system with Windows 10.

The problem with trying again and starting over every couple of years is that you never really go anywhere. Now that Windows Mobile is almost the same as desktop Windows, please Microsoft, can we bring back all the old really-useful features that we once knew?

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