[13][14][15][16][17] Pocket PC 2000, originally codenamed "Rapier", was released on April 19, 2000, and was based on the Windows CE 3.0 kernel.

Newly added or updated programs include[23][24][25][26] Windows Media Player 8 with streaming capability; MSN Messenger, and Microsoft Reader 2, with Digital rights management support.

Connectivity was improved with file beaming on non-Microsoft devices such as Palm OS, the inclusion of Terminal Services and Virtual private networking support, and the ability to synchronize folders.

Other upgrades include an enhanced UI with theme support and savable downloads and WAP in Pocket Internet Explorer.

Multimedia improvements included MIDI file support as ringtones in Phone Edition and Windows Media Player 9.0 with streaming optimization.

This upgrade allows users to switch between portrait and landscape modes and introduces a single-column layout in Pocket Internet Explorer.

Among new hardware features were enhanced Bluetooth support, default QWERTY keyboard-support and a management interface for Global Positioning System (GPS).

Business customers benefited from a new error reporting facility similar to that present in desktop and server Windows systems.

Caller ID now supports photos so a user can apply an image to each contact to show when a call is received.

Developers and users also have access to Microsoft SQL Server 2005 Compact Edition for storage and retrieval of information.

Communication abilities were further enhanced with a new Microsoft Bluetooth Stack and VoIP (Internet calling) support with acoustic echo cancellation and MSRT audio codec.

[42] Among other improvements:[43] 320×320 and 800×480 (WVGA) screen resolution support (The S01SH or "Em One" by Sharp was the first and only device to have an 800×480 screen on WM5),[44] Improved Remote Desktop access[45] (available for only certain Pocket PCs),[46] Customer Feedback option,[47] Smartfilter for searching within programs and Unlicensed Mobile Access (UMA) support for select operators.

[48] Several other changes such as threaded SMS, full page zooming in Internet Explorer and 'Domain Enroll' were also added, along with a "mobile" version of the Microsoft OneNote program and an interactive "Getting Started" wizard.

[56] This update includes some significant new added features, such as a revamped GUI, a new Today screen resembling that of Microsoft's Zune player with vertically scrollable labels (called 'Titanium') in terms of functionality with a styling similar to that of Windows 7.

[58] Along with Windows Mobile 6.5, Microsoft announced several cloud computing services codenamed "SkyBox", "SkyLine", "SkyMarket".

[62] Some reviewers have noted interface inconsistencies, with some applications having small buttons making them harder to operate using only a finger.

As such no major upgrades were planned or released, although three minor updates; 6.5.1, 6.5.3 and 6.5.5; were made to satisfy consumers during the transition period.

[71] 6.5.3 continues the trend of attempting to provide a more finger-friendly user interface with several new usability features such as native support for multitouch; although device maker HTC Corporation created proprietary work-arounds to allow multi-touch to work on some applications it installed on its HD2 handset (However, Microsoft applications on this handset, such as the Internet Explorer web browser, did not support multi-touch.

"[73] Internet Explorer Mobile 6 has also received some major updates including decreased page load time, improved memory management and gesture smoothing.

[81] From a technical standpoint Microsoft also specified various hardware and software requirements such as the inclusion of a touchscreen and a directional pad or touchpad.

Microsoft's use of the term "Smartphone" includes only more specific hardware devices that differ from Pocket PC phones.

Such Smartphones were originally designed without touchscreens, intended to be operated more efficiently with only one hand, and typically had lower display resolution than Pocket PCs.

In Q1 2003, Windows Mobile was the third largest operating system in the smart handheld market, behind Symbian and Palm OS.

[98] The New York Times reported in 2009 that Windows Mobile "[was] foundering", as cellphone makers desert it in favor of Google's Android phone platform.

[99] It cited the difficulties in Microsoft's business model, which involves charging handset manufacturers up to $25 for each copy of Windows Mobile, while rival Google gives away Android for free.

Microsoft also distributed Visual Studio 2008 / 2005 Professional Editions, and server/database counterparts to students as downloads free of charge via its DreamSpark program.

[109] Third party integrated development environments could also be used to write software such as Lazarus, Resco MobileForms Toolkit,[110] Lexico, NS Basic and Basic4ppc.

Microsoft had tolerated this procedure for some time but decided in February 2007 to ask developers to take their OS images off the net, which in turn raised discussions.

[113] On July 5, 2009, Microsoft opened a third-party application distribution service called Windows Marketplace for Mobile.

[8] In the early years of Windows Mobile devices were able to be managed and synced from a remote computer using ActiveSync; a data synchronization technology and protocol developed by Microsoft, originally released in 1996.