The first independent version of Microsoft Windows, version 1.0, released on 20 November 1985, lacked a degree of functionality and achieved little popularity. It was originally going to be called Interface Manager, but Rowland Hanson, the head of marketing at Microsoft, convinced the company that the name Windows would be more appealing to consumers.

Windows 1.0 was not a complete operating system, but rather extended MS-DOS, and shared the latter's inherent flaws and problems. The first version of Microsoft Windows includes a simple graphics painting program called Windows Paint, Windows Write, a simple word processor, and also includes the MS-DOS Executive, an appointment calendar, a card filer, a notepad, a clock, a control panel, a terminal, Clipboard and RAM driver. It also includes a game called Reversi.

Microsoft Windows version 2 came out on 9 December 1987, and proved slightly more popular than its predecessor. Much of the popularity for Windows 2.0 came by way of its inclusion as a "run-time version" with Microsoft's new graphical applications, Excel and Word for Windows. They can be run from MS-DOS, executing Windows for the duration of their activity, and closing down Windows upon exit.

Microsoft Windows received a major boost around this time when Aldus PageMaker appeared in a Windows version, having previously run only on Macintosh. Some computer historians date this, the first appearance of a significant and non-Microsoft application for Windows, as the beginning of the success of Windows.

Microsoft Windows scored a significant success with Windows 3.0, released in 1990. In addition to improved capabilities given to native applications, Windows also allows a user to better multitask older MS-DOS based software compared to Windows/386, thanks to the introduction of virtual memory. It made PC compatibles serious competitors to the Apple Macintosh.

This benefited from the improved graphics available on PCs by this time (by means of VGA video cards), and the Protected/Enhanced mode which allowed Windows applications to use more memory in a more painless manner than their DOS counterparts could. Windows 3.0 can run in any of Real, Standard, or 386 Enhanced modes, and is compatible with any Intel processor from the 8086/8088 up to 80286 and 80386.

Windows 3.0 tries to auto detect which mode to run in, although it can be forced to run in a specific mode using the switches: /r (real mode), /s ("standard" 286 protected mode) and /3 (386 enhanced protected mode) respectively. This was the first version to run Windows programs in protected mode, although the 386 enhanced mode kernel was an enhanced version of the protected mode kernel in Windows/386.

Due to this backward compatibility, Windows 3.0 applications also must be compiled in a 16-bit environment, without ever using the full 32-bit capabilities of the 386 CPU.

A "multimedia" version, Windows 3.0 with Multimedia Extensions 1.0, was released several months later. This was bundled with "multimedia upgrade kits", comprising a CD-ROM drive and a sound card, such as the Creative Labs Sound Blaster Pro. This version was the precursor to the multimedia features available in Windows 3.1 and later, and was part of the specification for Microsoft's specification for the Multimedia PC.

The features listed above and growing market support from application software developers made Windows 3.0 wildly successful, selling around 10 million copies in the two years before the release of version 3.1. Windows 3.0 became a major source of income for Microsoft, and led the company to revise some of its earlier plans.