Windows 8 Operating System _ Dual-boot Windows 8 with UBUNTU 25

1. Hi Copilot , I have a 500 GB Hard Disk Drive and I would like to have 2 different Operating System working in that 500 GB Hard Disk Drive , that is , Windows 8 Operating System and UBUNTU 25 , meaning , I would like to do a dual-boot between Windows 98 Operating System and Linux Operating System DEBIAN 13 . Copilot , could you please give me some technical tips or a step-by-step procedure how to do it . THANKS Copilot.

MICROSOFT Copilot Answer

Dual-boot overview with modern Linux and legacy Windows

It sounds like you’re mixing a few options: Windows 8 vs Windows 98, Ubuntu 25 vs Debian 13. Here’s the crux: dual-booting a modern Linux (Ubuntu 25 or Debian 13) with Windows 8 is straightforward; dual-booting with Windows 98 on modern hardware is highly impractical due to drivers, UEFI, GPT, and SATA issues. If Windows 98 is truly what you need (for old apps/games), I recommend virtualization for Win98 and a native install for Linux. If you meant Windows 8, I’ll give you the clean dual-boot steps below, plus notes for Debian 13.

Before you start

Backup everything: Use an external drive or cloud. You’ll be resizing partitions and installing bootloaders.
Decide the OS pair:
- If it’s Windows 8 + Ubuntu/Debian: proceed with the UEFI/GPT approach below (recommended). Debian Wiki linuxblog.io
- If it’s Windows 98 + Debian 13: use a VM for Windows 98 (e.g., VirtualBox/PCem), and dual-boot Linux with Windows 8 or 10 instead. Windows 98 does not support UEFI/GPT and has severe driver/compatibility limitations on modern systems.
Check firmware mode: Confirm if your PC uses UEFI (most modern systems) or legacy BIOS. UEFI + GPT keeps Windows Boot Manager and GRUB nicely isolated and makes the install order less critical. Debian Wiki

Disk planning for 500 GB HDD

Suggested layout (UEFI + GPT):
- EFI System Partition (ESP): 300–500 MB, FAT32, for bootloaders.
- Windows 8 partition: 200–300 GB NTFS (adjust to your needs).
- Linux root partition (/): 100–200 GB ext4.
- Linux swap: 4–8 GB (or a swapfile).
- Optional shared data: Remaining space NTFS for cross-access.
If the disk is MBR and you want UEFI/GPT: Convert MBR→GPT only if you’re on Windows 10/11 using MBR2GPT and you verify UEFI support first. For Windows 8 systems, plan a clean install to GPT if you want UEFI; otherwise stay legacy/MBR. With UEFI + GPT, Windows and GRUB are isolated, and reinstalling Windows doesn’t overwrite GRUB records. Debian Wiki

Sources: Debian Wiki

Step-by-step: Windows 8 + Ubuntu 25 or Debian 13 (UEFI/GPT)

Prepare Windows

Update and backup: Ensure Windows is healthy; disable BitLocker/Device Encryption temporarily if present, as it can complicate dual-boot changes. Debian Wiki
Shrink Windows partition: In Disk Management, shrink to free space for Linux (at least 60–100 GB).
Fast startup/hibernation off: Disable Windows fast startup to avoid filesystem issues when swapping OS.

Create Linux installer

Download ISO: Ubuntu 25 or Debian 13 from official sites.
Make bootable USB: Use Rufus or balenaEtcher. Choose “GPT + UEFI” if you’re in UEFI mode.

BIOS/UEFI settings

Boot mode: Set firmware to UEFI. Keep Secure Boot enabled if your distro supports it (Ubuntu usually does; Debian can with signed shim, but if you hit issues, disable Secure Boot temporarily). Debian Wiki linuxblog.io

Install Linux

Boot USB: Select the installer in UEFI boot menu.
Partitioning:
- Use the existing ESP (do not format; mount as /boot/efi).
- Create ext4 root (/) in the free space.
- Create swap (or plan a swapfile).
Bootloader: Install GRUB to the EFI system partition (the installer will handle this).
Finish and reboot: You should see GRUB with entries for Linux and Windows. Modern guides show this flow clearly for Ubuntu/Debian on UEFI systems. linuxblog.io Debian Wiki

Post-install

Update GRUB: In Linux, run a grub update command (the installer often does this).
Windows boot entry: If Windows doesn’t show in GRUB, boot Linux and add it via os-prober or manually; many Debian/Ubuntu guides cover recovering entries and UEFI nuances. Debian Wiki linuxblog.io
Re-enable BitLocker (optional): Once confirmed stable; note BitLocker can complicate boot changes and GRUB access. Debian Wiki

Sources: Debian Wiki linuxblog.io

Notes specific to Debian 13

UEFI + GPT is recommended: It isolates Windows Boot Manager and GRUB, making installation order less important and reducing bootloader conflicts. Debian Wiki
Installer flow: The Debian installer will let you select the ESP for /boot/efi and install GRUB accordingly. Community guides and walkthroughs cover the exact screens and common pitfalls for Debian 13 dual-boot with Windows. YouTube Debian Wiki

Sources: YouTube Debian Wiki

If you truly need Windows 98

Why dual-boot is impractical: Windows 98 lacks UEFI support, expects IDE controllers, and has poor drivers for SATA, modern GPUs, and large disks. It doesn’t understand GPT partitions.
Practical route:
- Install Debian 13 (or Ubuntu) natively.
- Run Windows 98 inside a VM (VirtualBox, VMware, or PCem/86Box for better legacy hardware emulation).
- Share files via ISO/virtual disks or network emulation.

Common pitfalls and fixes

Missing Windows in GRUB: Boot into Linux and run update-grub or add a manual GRUB chainloader entry for the Windows EFI file.
Secure Boot conflicts: If Linux won’t boot under Secure Boot, disable it, finish setup, then optionally re-enable with signed bootloader support. Debian Wiki
Clock/time issues: Set both OSes to use UTC or configure Windows to use UTC to avoid time drift.
File access between OSes: Use an NTFS data partition for shared storage.

Want me to tailor this?

Tell me which exact pair you want:

Windows 8 + Ubuntu 25
Windows 8 + Debian 13
Windows 98 (in VM) + Debian 13 native

And whether your system is UEFI or legacy BIOS. I’ll map precise partition sizes, installer screens, and GRUB entries for your 500 GB drive.

2.Copilot , I guess you are right ........ I have been a little mixed up .......... actually all I wanted is ........ with that 500 GB Hard Disk Drive ....... I wanted to do a dual-boot between Windows 8 Operating System and UBUNTU 25 Operating System ......... having said that I hope you could provide me some details regarding the step-by-step procedure on how to do that . THANKS Copilot.

MICROSOFT Copilot Answer

Great question — this is exactly the kind of detail that makes or breaks a smooth dual‑boot setup 👍.

Here’s the key distinction:

🖥️ Option 1: Install Windows 8 first, then shrink

Recommended approach.
Install Windows 8 normally, letting it use the full disk (or a large partition).
Once Windows is installed and running, open Disk Management and shrink the Windows partition to free up space for Ubuntu.
Then install Ubuntu into that free space.
Why? Because Windows tends to overwrite bootloaders if installed after Linux. Installing Windows first avoids headaches, and shrinking afterward is safe and supported.

🖥️ Option 2: Pre‑partition before Windows install

You could partition the disk before installing Windows, leaving unallocated space for Ubuntu.
But Windows sometimes ignores or overwrites custom layouts during installation, especially if you’re not careful with the installer options.
This method is less reliable unless you’re very comfortable with manual partitioning.

✅ Best practice

Install Windows 8 first.
Let it take the whole disk (or most of it).
Shrink the partition afterward using Disk Management.
Then install Ubuntu 25 into the freed space.
This ensures Windows boot files are set up cleanly, and Ubuntu’s GRUB bootloader will detect Windows automatically when installed second.

So in short: install Windows 8 first, then shrink the partition afterward. That’s the standard and safest way to set up a dual‑boot with Ubuntu.

Would you like me to sketch out a partition size plan for your 500 GB drive (e.g., how much space to give Windows vs Ubuntu vs shared storage)?

My journey with the Linux Operating System

Sunday, 23 November 2025