Blast from the Past: Borland C++ on Windows 98

My first exposure to C and C++ was a little over 20 years ago. I remember it being some version of Borland C++, either 4.x or 5.x, running on Windows 95. I didn’t have a mentor, so I did the best I could slowly working through what was probably a poorly written beginner C++ book, typing out the examples and exercises with little understanding. Since I didn’t learn much from the experience, there was a 7 or 8 year gap before I’d revisit C and C++ in college.

I thought it would be interesting to revisit this software, to reevaluate it from a far more experienced perspective. Keep in mind that C++ wasn’t even standardized yet, and the most recent C standard was from 1989. Given this, what was it like to be a professional software developer using a Borland toolchain on Windows 20 years ago? Was it miserable, made bearable only by ignorance of how much better the tooling could be? Or maybe it actually wasn’t so bad, and these tools are better than I expect?

Ultimately my conclusion is that it’s a little bit of both. There are some significant capability gaps compared to today, but the core toolchain itself is actually quite reasonable, especially for the mid 1990s.

The setup

Before getting into the evaluation, let’s discuss how I got it all up and running. While it’s technically possible to run Windows 95 on a modern x86-64 machine thanks to the architecture’s extreme backwards compatibility, it’s more compatible, simpler, and safer to virtualize it. Most importantly, I can emulate older hardware that will have better driver support.

Despite that early start in Windows all those years ago, I’m primarily a Linux user. The premier virtualization solution on Linux these days is KVM, a kernel module that turns Linux into a hypervisor and makes efficient use of hardware virtualization extensions. Unfortunately pre-XP Windows doesn’t work well on KVM, so instead I’m using QEmu (with KVM disabled), a hardware emulator closely associated with KVM. Since it doesn’t take advantage of hardware virtualization extensions, it will be slower. This is fine since my goal is to emulate slow, 20+ year old hardware anyway.

There’s very little practical difference between Windows 95 and Windows 98. Since Windows 98 runs a lot smoother virtualized, I decided to go with that instead. This will be perfectly sufficient for my toolchain evaluation.


To get started, I’ll need an installer for Windows 98. I thought this would be difficult to find, but there’s a copy available on the Internet Archive. I don’t know how “legitimate” this is, but it works. Since it’s running in a virtual machine without network access, I also don’t really care if this copy is somehow infected with malware.

Internet Archive: Windows 98 Second Edition

Also on the Internet Archive is a complete copy of Borland C++ 5.02, with the same caveats of legitimacy. It works, which is good enough for my purposes.

Internet Archive: Borland C++ 5.02

Thank you Internet Archive!


I’ve got my software, now to set up the virtualized hardware. First I create a drive image:

$ qemu-image create -fqcow2 win98.img 8G

I gave it 8GB, which is actually a bit overkill. Giving Windows 98 a virtual hard drive with modern sizes would probably break the installer. This sort of issue is a common theme among old software, where there may be complaints about negative available disk space due to signed integer overflow.

I decided to give the machine 256MB of memory (-m 256). This is also a little excessive, but I wanted to be sure memory didn’t limit Borland’s capabilities. This amount of memory is close to the upper bound, and going much beyond will likely cause problems with Windows 98.

For the CPU I settled on a Pentium (-cpu pentium). My original goal was to go a little simpler with a 486 (-cpu 486), but the Windows 98 installer kept crashing when I tried this.

I experimented with different configurations for the network card, but I couldn’t get anything to work. So I’ve disabled networking (-net none). The only reason I’d want this is that it would be easier to move files in and out of the virtual machine.

Finally, here’s how I ran QEmu. The last two lines are only needed when installing.

$ qemu-system-x86_64 \
    -localtime \
    -cpu pentium \
    -no-acpi \
    -no-hpet \
    -m 256 \
    -hda win98.img \
    -soundhw sb16 \
    -vga cirrus \
    -net none \
    -cdrom "Windows 98 Second Edition.iso" \
    -boot d


Installation is just a matter of following the instructions. You’ll need that product key listed on the Internet Archive site.

That copy of Borland is just a big .zip file. This presents two problems.

  1. Without network access, I’ll need to figure out how to get this inside the virtual machine.

  2. This version of Windows doesn’t come with software to unzip this file. I’d need to find and install an unzip tool first.

Fortunately I can kill two birds with one stone by converting that .zip archive into a .iso and mounting it in the virtual machine.

unzip "BORLAND"
genisoimage -R -J -o borland.iso "BORLAND C++"

Then in the QEmu console (C-A-2) I attach it:

change ide1-cd0 borland.iso

This little trick of generating .iso files and mounting them is how I will be moving all the other files into the virtual machine.

Borland C++

The first thing I did was play around with with Borland IDE. This is what I would have been using 20 years ago.

Despite being Borland C++, I’m personally most interested in its ANSI C compiler. As I already pointed out, this software pre-dates C++’s standardization, and a lot has changed over the past two decades. On the other hand, C hasn’t really changed all that much. The 1999 update to the C standard (e.g. “C99”) was big and important, but otherwise little has changed. The biggest drawback is the lack of “declare anywhere” variables, including in for-loop initializers. Otherwise it’s the same as writing C today.

To test drive the IDE, I made a couple of test projects, built and ran them with different options, and poked around with the debugger. The debugger is actually pretty decent, especially for the 1990s. It can be operated via the IDE or standalone, so I could use it without firing up the IDE and making a project.

The toolchain includes an assembler, and I can inspect the compiler’s assembly output. To nobody’s surprise this is Intel-flavored assembly, which is very welcome. Imagining myself as a software developer in the mid 1990s, this means I can see exactly what the compiler’s doing as well as write some of the performance sensitive parts in assembly if necessary.

The built-in editor is the worst part of the IDE, which is unfortunate since it really spoils the whole experience. It’s easy to jump between warnings and errors, it has incremental search, and it has good syntax highlighting. But these are the only positive things I can say about it. If I had to work with this editor full-time, I’d spend my days pretty irritated.

Switch to command line tools

Like with the debugger, the Borland people did a good job modularizing their development tools. As part of the installation process, all of the Borland command line tools are added to the system PATH (reminder: this is a single-user system). This includes compiler, linker, assembler, debugger, and even an incomplete implementation of make.

With this, I can essentially pretend the IDE doesn’t exist and replace that crummy editor with something better: Vim.

The last version of Vim to support MS-DOS and Windows 95/98 is Vim 7.3, released in 2010. I download those binaries, trim a few things from my .vimrc, and smuggle it all into my virtual machine via a virtual CD. I’ve now got a powerful text editor in Windows 98 and my situation has drastically improved.

Since I hardly use features added since Vim 7.3, this feels right at home to me. I can invoke the build from Vim, and it can populate the quickfix list from Borland’s output, so I could actually be fairly productive in these circumstances! I’m honestly really impressed with how well this all works together.

At this point I only have two significant annoyances:

  1. Borland’s command line tools belong to that category of irritating programs that print their version banner on every invocation. There’s not even a command line switch to turn this off. All this noise is quickly tiresome. The Visual Studio toolchain does the same thing by default, though it can be turned off (-nologo). I dislike that some GNU tools also commit this sin, but at least GNU limits this to interactive programs.

  2. The Windows/DOS command shell and console is even worse than it is today. I didn’t think that was possible. This is back when it was still genuinely DOS and not just pretending to be (e.g. in NT). The worst part by far is the lack of command history. There’s no using the up-arrow to get previous commands. There’s no tab completion. Forward slash is not a substitute for backslash in paths. If I wanted to improve my productivity, replacing this console and shell would be the first priority.

Update: In an email, Aristotle Pagaltzis informed me that Windows 98 comes with DOSKEY.COM, which provides command history for COMMAND.EXE. Alternatively there’s Enhanced, an open source, alternative implementation that also provides tab completion for commands and filesnames. This makes the console a lot more usable (and, honestly, in some ways better than the modern defaults).

Building Enchive with Borland

Last year I wrote a backup encryption tool called Enchive, and I still use it regularly. One of my design goals was high portability since it may be needed to decrypt something important in the distant future. It should be as bit-rot-proof as possible. In software, the best way to future-proof is to past-proof.

If I had a time machine that could send source code back in time, and I sent Enchive to a competant developer 20 years ago, would they be able to compile it and run it? If the answer is yes, then that means Enchive already has 20 years of future-proofing built into it.

To accomplish this, Enchive is 3,300 lines of strict ANSI C, 1989-style, with no dependencies other than the C standard library and a handful of operating system functions — e.g. functionality not in the C standard library. In practice, any ANSI C compiler targeting either POSIX, or Windows 95 or later, should be able to compile it.

My Windows 98 virtual machine includes an ANSI C compiler, and can be used to simulate this time machine. I generated an “amalgamation” build (make amalgamation) — essentially a concatenation of all the source files — and sent this into the virtual machine. Before Borland was able to compile it, I needed to make three small changes.

First, Enchive includes stdint.h to get fixed-width integers needed for the encryption routines. This header comes from C99, and C89 has no equivalent. I anticipated this problem from the beginning and made it easy for the person performing the build to correct it. This header is included exactly once, in config.h, and this is placed at the top of the amalgamation build. The include only needs to be replaced with a handful of manual typedefs. For Borland that looks like this:

typedef unsigned char    uint8_t;
typedef unsigned short   uint16_t;
typedef unsigned long    uint32_t;
typedef unsigned __int64 uint64_t;

typedef long             int32_t;
typedef __int64          int64_t;

#define INT8_C(n)   (n)
#define INT16_C(n)  (n)
#define INT32_C(n)  (n##U)

Second, in more recent versions of Windows, GetFileAttributes() can return the value INVALID_FILE_ATTRIBUTES. Checking for an error that cannot happen is harmless, but this value isn’t defined in Borland’s SDK. I only had to eliminate that check.

Third, the CryptGenRandom() interface isn’t defined in Borland’s SDK. This is used by Enchive to generate keys. MSDN reports this function wasn’t available until Windows XP, but it’s definitely there in Windows 98, exported by ADVAPI32.dll. I’m able to call it, though it always reports an error. Perhaps it’s been disabled in this version due to cryptographic export restrictions?

Regardless of what’s wrong, I ripped this out and replaced it with a fatal error. This version of Enchive can’t generate new keys — unless derived from a passphrase — nor encrypt files, including the use of a protection key to encrypt the secret key. However, it can decrypt files, which is the important part that needs to be future-proofed.

With this three changes — which took me about 10 minutes to sort out — Enchive builds and runs, and it correctly decrypts files I encrypted on Linux. So Enchive has at least 20 years of past-proofing! The screenshot at the top of this article shows it running successfully in an MS-DOS console window.

What’s wrong? What’s missing?

I mentioned that there were some gaps. The most obvious is the lack of the standard POSIX utilities, especially a decent shell. I don’t know if any had been ported to Windows in the mid 1990s. But that could be solved one way or another without too much trouble, even if it meant doing some of that myself.

No, the biggest capability I’d miss, and which wouldn’t be easily obtained, is Git, or a least a decent source control system. I really don’t want to work without proper source control. Git’s support for Windows is second tier, and the port to modern Windows is already a bit of a hack. Getting it to run in Windows 98 would probably be a challenge, especially if I had to compile it with Borland.

The other major issue is the lack of stability. In this experiment, I’ve been seeing this screen a lot:

I remember Windows crashing a lot back in those days, and it certainly had a bad reputation for being unstable, but this is far worse than I remembered. While the hardware emulator may be somewhat at fault here, keep in mind that I never installed third party drivers. Most of these crashes are Windows’ fault. I found I can reliably bring the whole system down with a single GetProcAddress() call on a system DLL. The only way I can imagine this instability was so tolerated back then was general ignorance that computing could be so much better.

I was tempted to write this article in Vim on Windows 98, but all this crashing made me too nervous. I didn’t want some stupid filesystem corruption to wipe out my work. Too risky.

A better alternative

If I was stuck working in Windows 98 — or was at least targeting it as a platform — but had access to a modern tooling ecosystem, could I do better than Borland? Yes! Programs built by Mingw-w64 can be run even as far back as Windows 95.

Now, there’s a catch. I thought it would be this simple:

$ i686-w64-mingw32-gcc -Os hello.c

But when I brought the resulting binary into the virtual machine it crashed when ran it: illegal instruction. Turns out it contained a conditional move (cmov) which is an instruction not available until the Pentium Pro (686). The “pentium” emulation is just a 586.

I tried to disable cmov by picking the specific architecture:

$ i686-w64-mingw32-gcc -march=pentium -Os hello.c

This still didn’t work because the statically-linked part of the CRT contained the cmov. I’d have to recompile that as well.

I could have switched the QEmu options to “upgrade” to a Pentium Pro, but remember that my goal was really the 486. Fortunately this was easy to fix: compile my own Mingw-w64 cross-compiler. I’ve done this a number of times before, so I knew it wouldn’t be difficult.

I could go step by step, but it’s all fairly well documented in the Mingw-64 “howto-build” document. I used GCC 7.3 (the latest version), and for the target I picked “i486-w64-mingw32”. When it was done I could compile binaries on Linux to run in my Windows 98 virtual machine:

$ i486-w64-mingw32-gcc -Os hello.c

This should enable quite a bit of modern software to run inside my virtual machine if I so wanted. I didn’t actually try this (yet?), but, to take this concept all the way, I could use this cross-compiler to cross-compile Mingw-w64 itself to run inside the virtual machine, directly replacing Borland C++.

And the only thing I’d miss about Borland is its debugger.

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Chris Wellons