Roads not taken 1985 → 2006 Lost to lock-in

OS/2

The Better Windows Than Windows

IBM and Microsoft, later IBM alone

How does an operating system backed by IBM, technically ahead of its rival and once co-developed by Microsoft, lose to that rival?

The world it was born into

By 1985 the IBM PC and its clones ran DOS, a simple operating system Microsoft licensed to IBM and, crucially, to everyone else. DOS ran one program at a time, could use only a small amount of memory directly and offered no protection: a misbehaving program could crash the whole machine. Everyone agreed the PC needed something better. Apple had shown a graphical interface with the Macintosh in 1984. Microsoft was working on Windows, a graphical layer on top of DOS, whose first version in 1985 made little impression.

IBM and Microsoft were bound together. IBM had created the PC standard; Microsoft supplied its software. In August 1985 they signed an agreement to develop the next operating system together. It became OS/2.

The bet

OS/2 was ambitious for a personal computer: multitasking, protected memory so programs could not crash each other, and later a graphical interface called Presentation Manager. It was meant to be the professional successor to DOS, especially for the corporations that were IBM’s core customers. When IBM announced its new PS/2 computers in April 1987, OS/2 was announced alongside them.

The bet was that the combined weight of IBM and Microsoft would define the next platform, as it had defined the first.

Why it made sense

Few people in 1987 would have bet against IBM and Microsoft together. IBM was the largest computer company in the world, with unmatched relationships with corporate buyers. Microsoft controlled the operating system on most PCs. OS/2’s technical design was sound and in several respects more advanced than anything else available for PCs. Corporate customers wanted stability and multitasking.

How it lost

The first problem was the processor. OS/2 was designed for the Intel 80286, which IBM had used in the PC/AT and in some PS/2 models. The 286 had a protected mode, but it ran old DOS programs poorly while in it. The 386, which arrived in PCs in 1986, could run several DOS programs at once in protected mode. Building for the 286 meant OS/2 ran existing DOS software badly, and existing software was what users had. OS/2 1.0, released in December 1987 without a graphical interface, also needed more memory than most PCs had, and memory was expensive.

The second problem was applications. Few were written for OS/2, so few people bought it, so few were written. This is path dependence in its most familiar form.

The third problem was Windows. In May 1990 Microsoft released Windows 3.0. It ran on top of DOS, on machines people already owned, and it made good use of the 386. It sold very well. Microsoft now had a successful product it controlled outright, and its interest in sharing a platform with IBM declined. The partnership broke up over 1990–91. Microsoft’s next-generation work, originally intended as OS/2 3.0, became Windows NT, released in 1993.

IBM continued alone, and did good work. OS/2 2.0, in 1992, and OS/2 Warp, in 1994, were stable, capable systems that could run DOS and Windows programs, often better than Windows itself. IBM marketed it as “a better DOS than DOS and a better Windows than Windows”. The slogan captured the strategy’s weakness: if Windows programs ran fine on OS/2, why would anyone write an OS/2 program? When Windows 95 arrived in August 1995 with a huge launch, broad manufacturer support and a new generation of applications, the contest was over. IBM stopped marketing OS/2 in 2005 and ended support at the end of 2006.

Explaining both the same way

The usual story credits Microsoft’s strategic skill and blames IBM’s bureaucracy. A symmetrical account looks at what each side optimised for.

IBM optimised for its own business: selling PS/2 hardware and serving corporate customers who valued stability and IBM support. Those priorities shaped the 286 decision and the emphasis on corporate features. Microsoft optimised for being on every PC from every manufacturer, which meant running on hardware people already owned and keeping the platform under its own control. When the market rewarded running on existing machines with existing software, Microsoft’s priorities matched the market and IBM’s did not. Technical quality was not the deciding factor; fit with users’ installed base was.

The partnership itself is a lesson in transaction costs. Two companies with diverging interests, jointly building a product whose value each wanted to capture, faced constant negotiation. Once Windows gave Microsoft a better option, the incentive to keep negotiating disappeared.

What the loss teaches

OS/2 shows that in platform markets the deciding question is rarely “which system is better?” It is “which system runs what I already have, and what will developers write for next?” OS/2 answered the first question badly in 1987 and answered it too well in 1992, by running Windows programs so well that it strengthened Windows.

It also shows the fragility of partnerships between companies whose long-term interests diverge. The agreement made sense for both in 1985. It stopped making sense for one of them in 1990.

Sources and limitations

This page relies on published histories of IBM and Microsoft and on Gordon Letwin’s technical account of OS/2’s design. Reasons for the 286 decision and for the partnership’s collapse are described differently by participants from each company; this page describes the decisions and their consequences rather than adjudicating motives. Sales figures are not given because reliable comparable figures were not verified for this page.

The minds involved

The forces at work

  1. Lock-in through applications

    Users bought operating systems to run applications, and developers wrote applications for the platform with the most users. DOS and then Windows had the users. Each year that OS/2 lacked native applications made the gap harder to close.

  2. The compatibility paradox

    OS/2 2.0's ability to run Windows programs well was a strength in reviews and a weakness in strategy. If Windows programs ran on OS/2, developers had little reason to write OS/2 programs, and users had little reason to switch. The winner's ecosystem grew inside the rival's product.

  3. A partnership of unequal interests

    IBM wanted an operating system that sold its PS/2 hardware and fitted its corporate customers. Microsoft wanted a platform it controlled across every manufacturer's machines. Joint development across those interests carried high coordination costs and invited a split once one partner had a better option.

  4. Organisations ship their shape

    Two companies with very different cultures, processes and goals jointly designing one system produced a product shaped by negotiation, with design choices that reflected each partner's priorities more than a single vision.

For people who build products

Decisions worth studying

3 decisions from this history, each with the situation, the alternatives, what happened and a verdict. Open one for the full case. The verdict says how a decision turned out, which is not the same as whether it was wise; see moral luck.

  1. 1985–1987 · IBM and Microsoft Weak process Backfired Jointly develop OS/2 as the successor to DOS, initially targeting the Intel 80286 processor. A new platform must make the old software run well before it can make new software worth writing.
    Situation
    IBM's PC/AT used the 286, and IBM's forthcoming PS/2 line included 286 machines. The 386, with far better support for running DOS programs in protected mode, was arriving; Compaq shipped a 386 PC in 1986.
    Alternatives
    Target the 386 from the start; extend DOS incrementally; let Microsoft lead with Windows.
    What happened
    OS/2 1.0 shipped in December 1987, without a graphical interface, and 1.1 added Presentation Manager in 1988. It was costly, demanding of memory and limited in running DOS programs, and adoption was slow.
    Verdict
    Tying the design to the 286, partly to protect installed hardware, limited the system's ability to run existing DOS software, the one thing most users needed.

    Pattern Compatibility becomes gravity

  2. 1990 · Microsoft Strong process Paid off After the success of Windows 3.0, shift strategic priority to Windows and away from joint OS/2 development. When customers adopt the option you control, partnership commitments can become a cost rather than an asset.
    Situation
    Windows 3.0, released in May 1990, sold strongly on existing DOS machines. Microsoft controlled Windows outright.
    Alternatives
    Continue committing to OS/2 with IBM; merge the two efforts.
    What happened
    The partnership ended. Microsoft's next-generation work became Windows NT; IBM continued OS/2 alone. Windows became the dominant PC operating system.
    Verdict
    Measured by Microsoft's interests, a clear-eyed reading of where users and developers were going.

    Pattern Users decide what the product is forDistribution beats elegance

  3. 1992–1994 · IBM Sound process Backfired Position OS/2 2.0 and Warp as "a better DOS than DOS and a better Windows than Windows", emphasising their ability to run DOS and Windows programs. Compatibility with a rival's platform buys users at the price of strengthening that platform.
    Situation
    OS/2 lacked native applications. Running existing software was the fastest way to attract users.
    Alternatives
    Concentrate on native OS/2 applications and a distinct identity; focus on corporate and server markets.
    What happened
    OS/2 earned respect and a loyal following, especially in business, but Windows 95 in 1995 drew consumers and developers. IBM ended marketing in 2005 and support at the end of 2006.
    Verdict
    A reasonable answer to the application gap that also removed developers' reasons to write native software. There may have been no winning move by then.

    Pattern Compatibility becomes gravityIncumbents absorb the challenger’s best idea

Nothing quite dies

What survived

  • Long service in banking, automated teller machines and other embedded and back-office systems, where stability mattered more than applications.
  • Third-party continuations such as eComStation and ArcaOS kept OS/2 running on modern hardware.
  • Microsoft's work on "OS/2 3.0" became the foundation of Windows NT, the core of every modern version of Windows.
  • The case remains a standard lesson in how application compatibility, not technical quality, decides platform contests.

Rise and fall

Timeline

  1. 1985 IBM and Microsoft sign a joint development agreement.
  2. 1986 Compaq ships a PC based on the Intel 386.
  3. 1987 OS/2 is announced with IBM's PS/2 line in April and ships in December.
  4. 1988 OS/2 1.1 adds the Presentation Manager graphical interface.
  5. 1990 Windows 3.0 ships in May and sells strongly; the partnership begins to break up.
  6. 1992 IBM releases OS/2 2.0, able to run DOS and Windows programs.
  7. 1993 Microsoft releases Windows NT.
  8. 1994 IBM releases OS/2 Warp 3.
  9. 1995 Windows 95 ships.
  10. 2006 IBM ends support for OS/2.

Take it to your team

Questions to ask

  • Does our platform run the software our customers already depend on, well?
  • In our partnerships, whose interests diverge first if one partner finds a better option?
  • Is compatibility with a competitor helping us, or growing their ecosystem inside our product?

Follow the thread

Connections

Where this comes from

Sources

  1. Paul Carroll, Big Blues. The Unmaking of IBM (Crown, 1993).
  2. Gordon Letwin, Inside OS/2 (Microsoft Press, 1988).
  3. Michael A. Cusumano and Richard W. Selby, Microsoft Secrets (Free Press, 1995).
  4. IBM, OS/2 Warp end of service announcement (2005).

How to cite

Shrikant Kumar. “OS/2: The Better Windows Than Windows.” Road not taken, Telos. https://shrikantk.com/roads-not-taken/os2/

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