Windows 98 SE in DOSBox-X for macOS and Windows 10/11

A system for running Windows 98 SE in DOSBox-X under macOS and modern Windows

This page describes a system based on DOSBox-X that runs Windows 98 SE (Second Edition) under recent versions of macOS (and, when it is ready, under Windows 10 or 11. Because Windows 98 SE is copyrighted software, the system will not run until you drop on its icon an .iso file containing an image of the Windows 98 SE installation CD distributed by Microsoft. No doubt you made an archive copy of that CD and can use it for unlocking the system.

You may download the macOS installer here. The installer and app are notarized. The installer will copy the app to your desktop, but you may move it anywhere, including your Applications folder. On a multi-user system, each user will have a separate copy of the hard disk image, while will be installed in the user's Library.

You may download the Windows 10/11 installer here. It will install the system into your user folder in current Windows.

Under DOSBox-X, it is normally difficult or impossible to share files between a DOSBox-X-based Windows 9x setup and the host computer. The system described on this page, however, makes it easy to send files to the Windows 98 SE desktop from the host computer when the system starts up, and to send files back to the host computer from the Windows 98 SE system when the system shuts down.

It also makes it possible to print from Windows 98 SE applications to the default printer on the host system, or to select from a list of printers installed on the host, or to "print" to a PDF on the host system's desktop. You can also exchange text between text and host using the clipboard. With some additional setup, you can also exchange files between guest and host using FTP while the system is running.

The system is a standard Windows 98 SE installation, updated with the Microsoft Windows Security Update CD February 2004, and with other minimal changes as follows:

• TCP networking is provided using an emulated NE2000 ethernet card
• WinSCP is installed for FTP file transfer to the host or remote sites
• The Adobe PostScript 4.1.3 printer driver is used for printing
• The Windows Scripting Host and TweakUI are installed
• The command prompt uses DOSKEY (installed by autoexec.bat)
• The Windows 98 Plus! add-ons are installed (with the Maintenance Wizard and anti-virus disabled, and the original startup and shutdown logos restored in place of the Plus! logos)
• Old versions of the Firefox and Opera browsers are installed, but won't be useful in the modern internet
• A folder named C:\Installers contains installation files for the programs listed above, plus installers for some other programs (Acrobat Reader, FileZilla, 7Z, AutoIt, etc.) which you can install or delete
• The startup sound has been disabled to avoid distortion (the system starts up at the fastest possible speed, distorting the system sound

The only third-party applications fully installed in the system are WinSCP, Firefox, and Opera; all can be removed from the Control Panel. (A few other applications, not yet installed, are in the C:\Installers folder, as noted above.). The only third-party driver installed is the Adobe PostScript driver.

To run Windows 98 SE under macOS:

Double-click the Windows98SE application. You will be prompted to unlock the system by dropping on it an .iso file containing an image of the Windows 98 SE installation CD. The file can have any name, but must have an .iso extension. One possible name might be "Windows 98 Second Edition.iso" (verbum sap.), but any shorter name will work well also.

After the application tells you that it is unlocked, simply run it again. The first time that it runs, it will ask permissions; grant those permissions. However, if you see a message saying that the application needs permission to receive keystrokes from other applications, you can click "Deny," because the application does not in fact need this permission; I don't know how to disable that prompt.

Windows 98 SE may crash with a blue screen the first time it starts up. If this happens, simply run it again. At the menu that offers to boot in Safe Mode, boot either in Safe Mode and then shut it down and restart; or boot in Normal Mode, which will probably work correctly.

Before you can use the mouse to double-click on anything in the macOS version of the system, you must press a key (any key) and click in the Windows 98 SE window (it doesn't matter which you do first).

To mount a CD image or floppy-disk image in Windows 98 SE, and to set other available options: hold down the Option key when launching the application and select the relevant item from the Options menu. For further details on adding a CD-ROM or floppy-disk image to the system, see a separate section below.

To run Windows 98 SE under Windows 10/11:

Run the installer, and then launch Windows98SE.exe. You will be prompted to drop on to the application icon (not the message box) an .iso file containing an image of the Windows 98 SE installation CD. The file can have any name, but must have an .iso extension. One possible name might be "Windows 98 Second Edition.iso" (verbum sap.), but any shorter name will work well also.

After the application tells you that it is unlocked, simply run it again. You may or may not need to press a key (any key) before you can double-click on anything on the Windows 98 SE desktop.

To mount a CD image in Windows 98 SE, see a separate section below.

Windows 7 warning: The application will run under Windows 7, but DOSBox-X will probably crash on exit. This seems to be the effect of a bug in DOSBox-X, and there is nothing I can do about it.

Keyboard shortcuts

These keyboard shortcuts control DOSBox-X while Wndows98SE is running. Use Alt in Windows, Option in macOS:

• Ctrl-Alt/Option-Enter : Toggle window and full-screen mode
• Alt-Pause : Pause Windows98SE (Windows 10/11 only)
• Ctrl-Alt/Option-F1 : Toggle DOSBox-X menu line
• Ctrl-Alt/Option-F4 : Paste ASCII text from host clipboard
• Ctrl-Alt/Option-F5 : Stop clipboard paste in progress
• Ctrl-Alt/Option-F6 : Send Ctrl-Esc (open Start Menu)
• Ctrl-Alt/Option-F10 : Capture/release mouse
• Ctrl-Alt/Option-F11 : Slow down emulation
• Ctrl-Alt/Option-F12 : Speed up emulation
• Ctrl-Shift-Alt/Option-Home : Restart Windows98SE (Windows 10/11 only)

File exchange between guest and host

Because of the way DOSBox-X is written, you cannot directly access a physical drive while the application is running. You can use these workarounds to exchange files between Windows 98 SE and the host system:

To exchange files between the Windows 98 SE guest desktop and the host system desktop:

• To send files from the host to the Windows 98 SE guest: drop the files on the Windows98SE application icon in macOS or the Windows98SE application icon in Windows 10/11. If Windows 98 SE is not running, it will start up, and the dropped files will be copied to the Windows 98 SE desktop. If Windows 98 SE is already running, the files will be copied to the destkop the next time Windows 98 SE starts up after the current session is shut down.
• To send files from the Windows 98 SE guest to the host desktop, while Windows 98 SE is running, drop the files into the Windows 98 SE desktop icon labeled "Copy to Host" or "Copy to macOS Host," which is a shortcut to a drive image (typically Drive D:) that you should only use for this purpose. When Windows 98 SE shuts down, you will be prompted to move the files to the host desktop. (If they are still in the drive image the next time you shut down Windows 98 SE, you may be prompted again to move them to the host desktop.)

To access files already in a folder on the host system (Windows 10/11 only):

• On a Windows host only, you can access files on the host system (in read-only mode) by doing the following before you launch Windows 98 SE:
• In a Windows 10/11 command prompt, enter a SUBST command that assigns a drive letter to a folder, like this: subst y: c:\temp
• In the Windows98SE folder, go to the DOSBox folder and open win98.conf for editing.
• In the [autoexec] section, below the line @echo off add the line mount f y: and save the file.
• When you launch Windows98SE, the files in the folder that you chose will be available as a drive letter (possibly f:, but possibly another letter). You can read the files and copy them to the Windows system, but you cannot save them back to the drive.

To exchange files between guest and host using a WebDav server on an NAS device:

• If you use a Network Attached Storage device, set up a WebDav server on the device, and enable SMB2 access. Note the port number used for http and https access.
• On your Windows 98 SE system, in My Computer, click Web Folders and create a web folder. For the address, use http://123.456.8.9:8888 but replace the IP address with your NAT device and the last four number with the port number.
• Follow the prompts.
• You can access the NAS server from macOS or Windows by connecting the server. Any files you save to the server from the guest are immediately accessible from the host, and vice versa.

To exchange files between guest and host using FTP (requires additional setup):

Under macOS:

• The App Store, install the free QuickFTP Server and open it.
• In the General tab, in the Root Path field, navigate to a macOS folder that you want to access from Windows 98 SE. Change the port number to 2121 (this is essential!)
• In the Authentication tab, enter your macOS username and password and decide which level of access you want to grant to Windows 98 SE.
• Return to the General tab, click Start Server and note the IP address that appears in the Status line (this is the IP address of your macOS system on your local network).
• In Windows 98 SE, start WinSCP (it has an icon on the Taskbar).
• In the Session window, for the Host Name, use the IP address of your macOS system; change the Port Number to 2121; enter your macOS User name and Password; change the Protocol to FTP; and click Login. You may want to save the configuriation.

Under Windows 10/11:

• Find and install the latest version of FileZilla Server. Select whichever options you prefer for its normal operation, and launch the application.
• From the Server menu, open the Administrative interface.
• Run the Network configuration wizard. When prompted to setup the Passive Mode Port Range, leave it as Any; click Next; check Use local IP for local connections; click Next; then Finish.
• From the Server menu, choose Configure.
• Under Rights management, choose Use other system user, and enter your username and password.
• In Users, select User is enabled. In Authentication, choose Use system credentials to log in; and enable Use system creditials also for accessing files and directories.
• Under Add a Mount Point: Virtual path should be / and Native path should be the path of the host folcer that you want to share with Windows 98 SE. Set access mode to Read + Write (if you prefer); check Apply permissions to subdirectories. If you want to be able to create folders from the FTP client in Windows 98 SE, then check Writable directory structure.
• Start the FileZilla server.
• If you do not know the IP address of your Windows 10/11 system, use the ipconfig command from a command prompt.
• In Windows 98 SE, start WinSCP (it has an icon on the Taskbar).
• In the Session window, for the Host Name, use the IP address of your Windows 10/11 system; change the Port Number to 2121; enter your Windows 10/11 User name and Password; change the Protocol to FTP; and click Login. You may want to save the configuriation.

Alternatively, under Windows 10/11, you can use a command-line tool running in Windows 98 SE. Enable and launch the Open SSH Server in Windows 10/11 (search the web for details). Download PuTTY from this address and run it in Windows 98. The server address is the IP of your Windows 10/11 system, and use port 22 for SSH.

Access a CD-ROM image or a floppy-disk image into Windows 98 SE

You can add a CD-ROM image file (in .iso format) or a floppy-disk image file (in .img format ) into the system in order to install software or access files on the image file.

Under macOS:

• Drop either a CD-ROM image file (in .iso format) or a floppy-disk image (in .img format) on the application icon and follow the prompts. The file that you dropped will be copied (not moved) into the application and will be availabvle from the My Computer window in Windows 98 SE.
• To remove the CD-ROM or floppy-disk image from the system, hold down the Option key when launching the application and choose the relevant menu item.
• You can also add a CD-ROM or floppy-disk image file by holding down the Option key when launching the application and choosing the relevant option. You will be prompted to navigate to the image file that you want to copy into the system.

Under Windows 10/11:

• Drop either a CD-ROM image file (in .iso format) or a floppy-disk image file (in .img format) on the application icon in Explorer and follow the prompts.
• You can replace the current CD-ROM image or floppy-disk by closing down Wndowsm 98 SE, then dropping a different image file.
• To remove the current CD-ROM image or floppy-disk image, hold down the Shift key when starting the application and follow the prompts.