Windows 3.1 (WFW)on

vintage and modern hardware

Hackware v2.2 (7 Sept 2016) By: Yeo Kheng Meng (yeokm1@gmail.com)http://yeokhengmeng.com/2016/09/windows-for-workgroups-3-11-on-vintage-and-modern-hardware-in-2016/

1

So what is Windows 3.1x?

• Windows 3.1x is a series of 16-bit operating systems by Microsoft for use on PCs.

• Windows 3.1 was released on April 6, 1992

• Windows for Workgroups 3.11 was released on August 11, 1993

• WFW first to have inbuilt networking facilities

• All Windows 3.1x versions requires ≥MS-DOS 3.1 to be installed first

• https://en.wikipedia.org/wiki/Windows_3.1x

2

Quick demo• Win3.1 user interface• Clock is an external app Winclock

• Graphics and Network Configuration• Play music with sound recorder• Internet access with IE5

3

Challenge Motivation

4

Microsoft Timeline of DOS/Windows

5

• New Technology (NT) • DOS-based and Windows 9x• PC-DOS (IBM Personal Computer Disk Operating System)• MS-DOS (Microsoft Disk Operating System)• Source 1: https://en.wikipedia.org/wiki/Timeline_of_Microsoft_Windows• Source 2: https://en.wikipedia.org/wiki/Timeline_of_DOS_operating_systems

PC-DOS1.0

(1981)

PC-DOS1.1

(1982)

PC-DOS2.0

(1983)

PC-DOS2.1

(1983)

PC-DOS3.0

(1984)

PC-DOS3.1

(1985)

PC/MS-DOS 3.2(1986)

MS-DOS3.3

(1987)

MS-DOS5.0

(1991)

MS-DOS6.0-6.2(1993)

MS-DOS6.22

(1994)

MS-DOS4.0

(1988)MS-DOS3.0-3.1(1984)

Installation Goals

1. No Virtual Machines. That’s cheating!2. Video driver. No 640x4803. Sound4. Network, for web-surfing

6

WFW3.11 system requirements• MS-DOS 3.1 or later• Intel 80386 (12 – 40 Mhz)• 5.25-inch (high density) or 3.5-inch floppy drive• EGA, VGA, SVGA, XGA, 8514/A, or Hercules video card or 100%

compatible card, and monitor• 3 MiB RAM (4 MB is recommended)

• 640K Conventional memory• 2048K Extended memory

• 6.2 MiB disk space (14.5 MiB recommended)• Mouse recommended

• Source1: https://support.microsoft.com/en-us/kb/32905• Source2: https://support.microsoft.com/en-us/kb/89333

7

Understanding the Memory Layout

• Intel 8086/8088 CPUs have 20 address lines• Max 220 bytes = 1MiB memory

• Conventional memory (640KiB)• Executable code• Very precious

• Upper Memory Area (384KiB)• System device addresses• Additional Expanded Memory (EMS) via bank-switching

• Extended Memory (XMS) (Everything else)• Includes 64KiB High Memory Area (HMA) due to loophole• Can put DOS code here to conserve conventional memory

8Image Source: https://en.wikipedia.org/wiki/File:IBM_PC_Memory_areas.svg

IBM Thinkpad 390e• Released in 1999 with Windows 98

• Win3.1 drivers provided by IBM

• Specifications• Intel Mobile Pentium II 300Mhz• Intel 440BX chipset• NeoMagic Media256AV 2.5MB VRAM• 384MB SDRAM• ESS Solo-1 Audio• 13.1” 1024×768• PATA hard drive (I used an SD card with SD-PATA converter)• CDROM + Floppy combo• Serial, Parallel, PS/2, USB 1.0, IrDA• 2x Cardbus slots

• No Ethernet• 4.5cm thickness• 3.4kg weight

• US$2700 in 1999• US$3900 today• SG$5300 today

9

Preparing the install media

• 4x DOS 6.22 diskettes

• 8x WFW 3.11 diskettes

• Mac OS X El Capitan does not support USB Floppy drives

• Download links:

• https://winworldpc.com/product/ms-dos/622

• https://winworldpc.com/product/windows-3/wfw-311 10

Video and Audio drivers?

11

• Video and audio drivers provided by IBM works flawlessly

• http://thinkpads.com/support/Thinkpad-Drivers/download.lenovo.com/lenovo/content/ddfm/390e.html

Network?

12

• First attempt: PCMCIA/Cardbus network adapter• Xircom Realport Cardbus Ethernet 10/100• Intel hosts Xircom drivers till today• https://downloadcenter.intel.com/product/50588/Xircom-CardBus-Ethernet-

10-100-Adapter-CBE-10-100BTX-

• IBM’s Cardbus’s drivers DID NOT WORK!!!

• Second attempt: Parallel Port network adapter• Xircom Pocket Ethernet PE3-10BT• Powered by PS/2 passthrough cable• DOS drivers from Intel’s website• https://downloadcenter.intel.com/product/50622/Xircom-Pocket-Ethernet-

III-Adapter-PE3-10Bx-

But where is the challenge?

13

Modern Lenovo Thinkpad T400

14

• Released in 2009 with Windows 7• Specifications

• Intel® Core™2 Duo processor T9400, 2.53 Ghz• Intel GM45 chipset• Intel GMA 4500MHD• 8 GB DDR3 RAM• Conexant HD Audio• 14.1” LED matte display with 1440×900• 240GB Samsung 850 Evo • SATA DVD-RW Multi• 3 USB2.0 ports, 1 IEEE1394, Gigabit Ethernet• Intel Wireless-AC 7260 2×2 dual-band with

Bluetooth 4 via mini-PCIe• 1 Cardbus slot and 1 ExpressCard slot• Last to support Thinkpad Advanced Mini Dock

• Thinkpad Advanced Mini Dock• 4x USB• PS/2 keyboard/mouse• LAN• Native Serial and Parallel• VGA, DVI

Universal Video driver for VMs

• Patched driver for VMware• 1024 x 768 with 256 colours (XGA)• Source: https://sites.google.com/site/chitchatvmback/misc 15

My sound card• Designed and assembled by yours truly• Based on 1989 Covox Speech Thing, parallel port sound card• CPU-driven R-2R resistor-ladder

16https://github.com/yeokm1/pcb-covox-amp-v2

Network• Intel Gigabit Ethernet DOS drivers

17

CONFIG.SYS and AUTOEXEC.BAT• Important DOS configuration files

• CONFIG.SYS• Loads drivers on startup

• HIMEM.SYS/HIMEX.EXE: Extended Memory Manager• DOS=HIGH: Load DOS to HMA to save conventional memory• CDROMDRV.SYS: Toshiba CD driver• POWER.EXE: Sends x86 HALT instruction to save CPU power when idle

• AUTOEXEC.BAT• Stands for automatic execution• Batch files that starts at end of DOS boot process

• MSCDEX.EXE/SHCDX33F.COM: Assign CD drive letter to driver• DOSKEY.COM: Terminal history, auto-completion• CTMOUSE: Modern DOS mouse drive for PS/2 mouse

• devicehigh and loadhigh -> HMA

18

HTTPS support• Obsolete: SSLv1 – SSLv3• In use: TLSv1.0 – TLSv1.2

• Problems• IE5 only supports SSLv3• Expired certificates

• Solution1.Use a proxy to “upgrade” SSL connection2.Use SSLStrip to replace HTTPS links as HTTP URLs• Both are man-in-the-middle (MITM) attacks

19

HTTPS solution 1: SSL upgrade• Use Squid proxy’s SSL BUMP• Did not complete due to complications and lack of time

20

TLS 1.1

Typical

MITMSSLv3 TLS 1.1

Client Web Server (s)

HTTPS solution 2: SSLstrip

• Modern browsers use HTTP Strict Transport Security (HSTS)• A website tells client must use HTTPS

• Some servers enforce HTTPS-only connection21

Client Web Server (s)

MITMRaspberry Pi 3

Google “Wikipedia”

Reply from Google:https://en.wikipedia.org/https://www.wikipedia.org/https://www.facebook.com/wikipedia/Reply from Google:

http://en.wikipedia.org/http://www.wikipedia.org/http://www.facebook.com/wikipedia/

http://en.wikipedia.org/

Google “Wikipedia”

http://en.wikipedia.org/

Replaces HTTPS links as HTTP URLs

Bonus section: Windows 1.0• Oldest Windows version released in 1985• Used updated version 1.04 released in 1987• I could not run the programs, causes system hang

22

Conclusion• External comments• Massive waste of time• Money down the drain• Hugely impractical

• My takeaways• Greater appreciation for modern computing• Intel and Microsoft spent lots of effort to maintain

backward compatibility.

• Visit my blog post for more details• http://yeokhengmeng.com/2016/09/windows-for-workgroups-3-11-on-

vintage-and-modern-hardware-in-2016/

23