Running .exe on Ubuntu: Wine vs Virtualization vs WSL

1. Introduction – The Need to Run .exe on Ubuntu and the Purpose of This Article

When migrating from Windows to Ubuntu, it’s not uncommon to have cases where you rely on essential business software, small utilities, or games that depend on “.exe (Windows executable file)”. However, because Ubuntu (Linux) differs from Windows in executable formats and system architecture, you cannot simply double‑click .exe to run it.
This article aims to organize practical options for the real‑world question “How to handle .exe on Ubuntu”, so readers can choose the method best suited to their environment and goals.

What We Want to Convey

• .exeWindows-only executable format (PE format)
• In addition, it shows that the main approaches for handling on Ubuntu can be broadly divided into the following three categories.
• Each has , , and if you can use a Windows host, tend to become realistic solutions easily, presenting such axes of judgment.

Goal of This Article

• Based on the reader’s requirements (the intended software, emphasis on performance and stability, setup effort, license and cost), they should be able to understand and .
• The actual can be reproduced locally, and can be handled.
• If it’s okay not to stick to , you can also notice the “alternative solution” called .

Intended Audience

• Ubuntu beginners to intermediate users who want to use a specific Windows app on Ubuntu
• “From ‘I just want to try it out for now’ to ‘I want to run it stably in business operations’,”
• I have already tried Wine and virtualization a bit, but I am troubled by .

Suggested Reading Approach

1. Basic Understanding
2. Overview of the Method
3. Detailed steps
4. Troubleshooting
5. Alternative
6. Decision Summary

Cautions (Before You Start Reading)

• All do not all run the same way. , , cause behavior changes.
• This article demonstrates a general and highly reproducible procedure, but it does not guarantee full compatibility with specific apps.and explain them.
• If you are operating in a corporate or organizational environment, be sure to check the .

2. What is an .exe file – Windows executable format basics

Before we get into handling .exe on Ubuntu (Linux), let’s clarify what .exe (and the Windows executable formats that include it) are, and why they differ from the Linux side.

2.1 What is the .exe/PE format

Overview of PE (Portable Executable) format

• On Windows, executable files (), libraries (), device drivers, etc., use the .
• The PE format is an extended version of the former COFF (Common Object File Format) and is a structure that includes the information required by the Windows OS loader (imports / exports, section structure, header information, etc.).
• A typical .exe file first has a structure consisting of ‘MS-DOS header’, ‘DOS stub’, ‘PE header’, ‘section group’. The DOS stub is a remnant of compatibility left to display ‘This program cannot be run’ in old DOS environments.

Key structures and functional elements (simplified version)

Thus, the PE format contains not only the core program code but also extensive header structures and reference/link information needed for execution on Windows.

2.2 Linux (Ubuntu) executable format: Characteristics of the ELF format

On Linux-based OSes (including Ubuntu), executable files primarily use the ELF (Executable and Linkable Format) format. Wikipedia

The ELF format is widely used on UNIX-like OSes and is designed with portability and flexibility in mind. Its main features are as follows.

• Supports various uses such as executable binaries, shared libraries, object files, etc.
• Header → Segment Section → Symbol Table, Reallocation Information, etc. Configuration
• The dynamic linker (ld.so, etc.) resolves libraries at runtime.
• The Linux kernel and loader mechanism are designed assuming the ELF format.

ELF works well with Linux execution, and standard tools such as readelf, objdump, and ldd support its analysis.

2.3 Differences between PE and ELF (why .exe does not run directly on Ubuntu)

The Windows PE format and the Linux ELF format have fundamentally different specifications from the ground up. These differences explain why a .exe cannot run directly on Ubuntu.

Key differences and the barrier to execution compatibility

In a StackOverflow discussion, PE and ELF are described as “different formats that serve the same purpose but are not mutually readable.” Stack Overflow Additionally, resources comparing PE and ELF focus on the structural and functional differences each supports. Wikipedia

In practice, a user attempted to convert an ELF to a PE, but concluded that “non-trivial native applications cannot be binary compatible” and that “Linux and Windows have different system calls,” making direct conversion impractical. Super User

2.4 Note: Why it is said that it “cannot run”

• On Ubuntu, double-clicking often results in errors such as ‘Not an ELF file with execute permissions’ or ‘Invalid file format’.
• Even when you look at with the terminal’s command, it displays “PE32 executable” etc., indicating that it is not a Linux executable format.
• .exe

3. Reasons .exe Cannot Run Directly on Ubuntu

In the previous section, we confirmed that .exe is a Windows‑specific executable format (PE format).
Here we will examine how those structural differences actually impact things and organize, from a more practical viewpoint, the reasons why .exe cannot be run directly on the Ubuntu (Linux) side.

3.1 Ubuntu’s “execution” and Windows’ “execution” are completely different

On Linux‑based OSes, including Ubuntu, the mechanism that launches programs (execution loader) is fundamentally different from Windows.
In other words, even though the operation “double‑click a file to run it” looks the same, the processing happening behind the scenes is completely different.

Windows Case

• The OS kernel parses the PE header of and loads the required DLLs (dynamic libraries).
• ntdll.dllkernel32.dlluser32.dll
• If it’s a GUI app, it is rendered through a window manager and processes user actions (clicks and key inputs).

Ubuntu (Linux) Case

• Executable files must be in , and the Linux kernel parses its header to load it.
• Dynamically link the shared library () and operate using the POSIX-compliant system call set (, , , , etc.).
• Because the file format and API structure are different, the PE format cannot be read and is rejected as “not an executable format”.

Therefore, even if you pass .exe directly to Ubuntu’s standard environment, the kernel recognizes it as a file with an unknown structure and refuses to execute it.

3.2 Example error when executing a command

In practice, if you double‑click .exe on Ubuntu or execute it in a terminal as ./program.exe, the following error is returned.

$ ./example.exe
bash: ./example.exe: cannot execute binary file: Exec format error

This is because Ubuntu’s execution loader cannot recognize the PE format.
This error does not indicate that the file itself is corrupted; it indicates that the OS does not know how to execute it.

3.3 Fundamental problem: the Windows API does not exist

The biggest reason .exe cannot run on Ubuntu is that the Windows API (Application Programming Interface) does not exist.

.exe files call Windows‑specific functions internally.
For example

CreateFileA();
MessageBoxW();
RegOpenKeyExW();

Functions such as these are Windows‑specific APIs contained in kernel32.dll and user32.dll.
Since Ubuntu lacks these, even if the file format could be read, there would be no target to call.

3.4 Differences in file system and environment variables

The file system structure and environment variable system differ greatly between Windows and Ubuntu.

Windows programs operate assuming a drive structure such as C: internally.
Since Ubuntu lacks this, many cases occur where the file path specification itself fails.

3.5 DLL dependencies and compatibility issues

Many .exe files appear to run on their own, but actually depend on multiple DLLs (dynamic link libraries).
For example, graphics might require d3d9.dll, audio dsound.dll, networking ws2_32.dll, and so on.

Ubuntu lacks these DLLs, and the Windows API itself is not implemented.
As a result, when a .exe file attempts to call these functions, errors like ‘function not found’ or ‘cannot load library’ occur.

3.6 CPU instruction set differences are minor, but architecture matters

Modern Ubuntu and Windows both run on the x86_64 (AMD64) architecture, so the CPU‑level instruction set is compatible.
However, because the execution environment at the OS level (system calls and address space handling) differs, software may not run even on the same hardware.

In particular, attempting to run a 32‑bit Windows .exe on 64‑bit Ubuntu is not supported without a compatibility layer such as Wine.

3.7 Summary: The inability to run .exe on Ubuntu is not a “technical barrier” but a “difference in design philosophy”

In short, the reason .exe does not run as‑is on Ubuntu is not a matter of capability, but because it was designed as a different OS.

• File formats differ (PE vs ELF)
• APIs differ (Windows API vs POSIX/Linux system calls)
• The structure of dynamic libraries is different (DLL vs .so)
• Paths, permissions, and environment variables differ
• The OS’s loading mechanism itself is different.

Therefore, if you want to run .exe on Ubuntu, you need to introduce an intermediate layer that absorbs these differences.
The tools that serve this purpose are described in the next section, such as ‘Wine’ and virtualization software.

4. Three Ways to Run .exe on Ubuntu

By now, you have understood why Ubuntu cannot run Windows .exe directly.
However, running them is not impossible.
By using appropriate “compatibility layers” or “virtual environments,” many Windows apps can run on Ubuntu.

Here we introduce three representative ways to run .exe on Ubuntu.
Compare each method’s features, pros, and cons to decide which one best suits your needs.

4.1 Using Wine (the most convenient compatibility layer)

What is Wine

Wine (Wine Is Not an Emulator) is, as its name implies, not an emulator but a compatibility layer that re-implements the Windows API on Linux.
In other words, it translates Windows instructions into Linux system calls, making it lighter and faster than virtualization or emulation.

Wine has been under development for over 20 years and can be easily installed from Ubuntu’s official repositories or a PPA.
Furthermore, using GUI front‑ends like PlayOnLinux or Bottles allows beginners to set up easily.

Installation steps (compatible with Ubuntu 22.04 / 24.04)

sudo dpkg --add-architecture i386
sudo apt update
sudo apt install wine64 wine32

Alternatively, if you want the latest version, add the official WineHQ repository.

sudo mkdir -pm755 /etc/apt/keyrings
sudo wget -O /etc/apt/keyrings/winehq-archive.key https://dl.winehq.org/wine-builds/winehq.key
sudo wget -NP /etc/apt/sources.list.d/ https://dl.winehq.org/wine-builds/ubuntu/dists/$(lsb_release -cs)/winehq-$(lsb_release -cs).sources
sudo apt update
sudo apt install --install-recommends winehq-stable

Basic usage

wine setup.exe

Or, right‑click the .exe on the desktop and choose “Open with Wine”.
On first launch, the ~/.wine directory is created, setting up a virtual C: drive structure.

Pros

Cons

Tip

Wine’s compatibility can be verified on the official database WineHQ AppDB.
Searching by application name shows compatibility levels such as “Gold” (works well) or “Bronze” (unstable).

4.2 Running via Virtual Machine / Emulator (stability‑focused)

If Wine doesn’t work well, or you need reliable operation for business use, using a virtual machine is realistic.
Typical examples are VirtualBox, VMware Workstation, and QEMU/KVM, among others.

How it works

Create a virtual hardware environment on Ubuntu and install a genuine Windows OS inside it.
In other words, it’s like running an additional Windows PC within Ubuntu.

Overview of steps

1. Install VirtualBox and otherssudo apt install virtualbox
2. Download Windows ISO image from Microsoft official website
3. Create a virtual machine and install from ISO
4. When Windows starts up, you can normally run

Pros

• Compatibility is the highest (almost all that run on Windows work)
• Can be stably operated as a dedicated environment
• Network, file sharing, snapshots, etc. are easy to manage

Cons

• High resource consumption (CPU, memory, storage)
• OS license required (Windows genuine version)
• It takes time to start up

Suitable Cases

• Business software and accounting software, etc., applications that require reliable operation.
• Software that requires 3D apps or special drivers
• If you want to develop and test Windows on Ubuntu

4.3 Using WSL (Windows Subsystem for Linux) (reverse approach)

The final method takes a slightly reverse approach.
If you are running Ubuntu inside Windows, you can run .exe through WSL (Windows Subsystem for Linux).

How it works

Ubuntu on WSL is actually a virtual Linux environment on Windows.
Thus, you can invoke .exe directly from the Ubuntu terminal.

notepad.exe

Typing this launches Windows “Notepad”.
Since WSL shares Windows kernel functionality, calls to .exe are passed through natively.

Pros

• You can call on Windows without any additional settings.
• File sharing between Linux and Windows is smooth
• Compatible with development environments (VSCode, Docker, etc.)

Cons

• It is limited to the environment of “using Ubuntu on Windows” (conversely, “running Windows on Ubuntu” is not possible)
• Some GUI apps and driver operations have restrictions.
• Not available in a pure Linux environment.

4.4 Which method to choose — Comparison table

4.5 Summary

To run .exe on Ubuntu, the best solution depends on how much compatibility and performance you need.

• Emphasis on convenience →
• Focus on stability and reproducibility →
• Windows dual-use faction →

By understanding these, you can make the optimal choice that fits your work environment and objectives.

5. Steps to Run .exe Using Wine (Ubuntu-compatible version)

From here, we will provide a detailed guide on the practical use of Wine, the simplest method to run .exe files on Ubuntu.
We will explain step by step, from installation to configuration, execution, and troubleshooting, so even first‑time users won’t get lost.

5.1 What is Wine — “a translation layer that reproduces Windows”

Wine stands for “Wine Is Not an Emulator” and is a compatibility layer that reproduces the Windows API on Linux.
In other words, it translates Windows instructions into “language that Linux can understand” and runs them.

The point is, it does not recreate the OS like a virtual machine, but runs directly on the Linux kernel.
This allows you to keep resource consumption low while achieving fast performance.

5.2 How to Install Wine (Ubuntu 22.04 / 24.04 supported)

First, install Wine to set up the runtime environment.
It is included in the standard repository, but if you want a newer stable version, use the official WineHQ repository.

① Enable 32‑bit support

sudo dpkg --add-architecture i386

Wine handles many 32‑bit applications, so enable the 32‑bit architecture even on a 64‑bit system.

② Add the official repository

sudo mkdir -pm755 /etc/apt/keyrings
sudo wget -O /etc/apt/keyrings/winehq-archive.key https://dl.winehq.org/wine-builds/winehq.key
sudo wget -NP /etc/apt/sources.list.d/ https://dl.winehq.org/wine-builds/ubuntu/dists/$(lsb_release -cs)/winehq-$(lsb_release -cs).sources
sudo apt update

③ Install the Wine package

sudo apt install --install-recommends winehq-stable

④ Verify installation

wine --version

If the above command shows a version such as wine-9.x, the installation is complete.

5.3 Initial configuration (first launch)

If you are using Wine for the first time, start the configuration wizard.

winecfg

As a result, the ~/.wine directory is created, and a Windows‑style virtual drive (C: drive) is automatically generated.

The structure looks like this:

~/.wine/
 ├─ drive_c/
 │   ├─ Program Files/
 │   ├─ windows/
 │   └─ users/
 └─ system.reg / user.reg etc.

Wine reproduces the Windows file structure here and installs and runs applications.

5.4 Running an .exe file

Method 1: Run from the command line

wine ~/Downloads/setup.exe

Method 2: Run from the file manager

.exe file, right‑click → choose “Open with Wine”.
It works the same way from the GUI.

For installers, a setup screen similar to Windows appears.
When the app is installed to C:Program Files, you can run it later as follows.

wine "C:\Program Files\AppName\app.exe"

5.5 Japanese fonts and garbled text mitigation

English apps run without issues, but Japanese apps may display garbled characters.
In that case, add Japanese fonts to Wine.

sudo apt install fonts-noto-cjk

Alternatively, copy msgothic.ttc or meiryo.ttc from Windows C:WindowsFonts to ~/.wine/drive_c/windows/Fonts to improve the situation.

5.6 Winetricks (Using handy tools)

winetricks is a helper tool for Wine that can easily install DLLs, fonts, and runtimes.

Installation

sudo apt install winetricks

Example: Install Visual C++ runtime

winetricks vcrun2015

This avoids “DLL not found” errors that occur in many applications.

5.7 Checking compatibility and using AppDB

Wine has an official database WineHQ AppDB where you can look up the status of each application.
Each app receives a rating rank such as:

By searching for the application name, you can view actual performance reports and recommended settings.

5.8 Common errors and solutions

5.9 Representative applications that can run with Wine

5.10 Summary

Wine is the most practical way to run .exe on Ubuntu, providing a balanced mix of
lightness, compatibility, and ease of installation.

However, some applications may work, so the trick is to check on AppDB beforehand and combine with winetricks as needed.

6. How to Use Virtual Machines, Emulators, and Containers

Wine runs many Windows applications, but not all of them work perfectly.
Especially, business software, accounting apps, games with 3D rendering, and apps that use drivers often have unstable behavior or fail to start under Wine.
In such cases, using Virtual Machine, Emulator, or Container is effective.

Here we introduce each mechanism and practical methods to execute .exe on Ubuntu.

6.1 What is a Virtual Machine — “Putting another Windows inside Ubuntu”

A Virtual Machine is a technology that recreates virtual PC hardware on Ubuntu and runs a full Windows on top of it.
Typical software includes the following:

• VirtualBox
• VMware Workstation Player
• QEMU / KVM

Architecture Overview

[Ubuntu Host OS]
 ├── VirtualBox (virtual hardware)
 │     ├── virtual CPU, memory, HDD
 │     └── [Windows Guest OS]
 │            └── .exe file execution

In other words, this is a form where you install a genuine Windows inside Ubuntu.
Thus, unlike Wine, there is no need for API translation, and it runs with nearly 100% compatibility.

6.2 Steps to Run Windows Using VirtualBox

① Install VirtualBox

sudo apt update
sudo apt install virtualbox

② Prepare Windows ISO file

Download the Windows 10 / 11 ISO image from the official Microsoft website.
License activation can be performed later (it works in the evaluation period).

③ Create a virtual machine

1. Start VirtualBox → Click the “New” button
2. Set name (Example: )
3. Type: Windows, Version: Windows 11 (64-bit)
4. Set memory to 2GB or more, disk size to 40GB or more.

④ Mount ISO and install

Select the created virtual machine, then
[Settings] → [Storage] → [Optical Drive] to specify the downloaded ISO.

When you start it, the Windows installer launches, and
you can perform the setup using the same steps as on a regular PC.

⑤ Run .exe

If Windows boots, you can run .exe files as usual.
When transferring files between the Ubuntu host, setting up a “Shared Folder” from the VirtualBox menu is convenient.

6.3 When Using VMware Workstation Player

VMware is faster than VirtualBox and is commonly used for business purposes.
On Ubuntu, you can easily install it by downloading the .bundle file from the official website.

chmod +x VMware-Player.bundle
sudo ./VMware-Player.bundle

The GUI installer launches, and you can set up Windows in the same way.

Advantages

• GPU virtualization support is good, and 3D apps also run relatively stably.
• Strong support for network, USB devices, etc.

Disadvantages

• Consumes many system resources
• Commercial use requires a paid license.

6.4 When Using QEMU/KVM (Advanced Users)

QEMU (pronounced “Keh-mu”) and KVM (Kernel-based Virtual Machine) are virtualization technologies that come standard with Ubuntu.
They are well suited for command-line management and automation, and are valuable in development and testing environments.

Installation

sudo apt install qemu-kvm libvirt-daemon-system virt-manager

Using the GUI

virt-manager can be launched to create and start virtual machines with a GUI similar to VirtualBox.

Features

• Very fast with native Linux virtualization
• Also supports CLI operations (including and )
• Virtual network and snapshot management is easy

6.5 Using Containers (Lightweight Alternative)

As a lighter-weight alternative to virtual machines, you can use containers (e.g., Docker + Wine).
It is not full virtualization, but containerizing a Wine environment increases reproducibility, and
allows the same configuration to be shared across multiple environments.

Example: Launch a Docker Container with Wine

docker run -it --rm 
  --name wine-env 
  -v ~/Downloads:/data 
  scottyhardy/docker-wine

You can execute the following inside the container:

wine /data/app.exe

Advantages

• Can be used without damaging the environment (does not affect the host)
• Easy to share settings with other developers
• Can also be integrated into automation (CI/CD)

Disadvantages

• The display settings for the GUI app are somewhat complicated (X11 forwarding is required)
• Audio, 3D acceleration, etc., have restrictions

6.6 Comparison of Methods

6.7 Which Method Should You Choose?

The recommended approaches by purpose are summarized as follows:

6.8 Summary

Virtual machines and emulators consume more resources than Wine, but they are characterized by overwhelmingly higher compatibility and stability.
Especially when handling business applications or driver-dependent software, a virtual environment running a real Windows is the most reliable approach.

By using Docker, QEMU/KVM, and similar tools, you can support more advanced operations and development.
In other words, this can be called the “final option” and “universal solution” for running .exe on Ubuntu.

7. How to Use WSL (Windows Subsystem for Linux)

What we have looked at so far is “Method to Run Windows Apps on Ubuntu”.
However, the opposite approach, i.e., Running Ubuntu inside Windows also exists.
That is WSL (Windows Subsystem for Linux).

If you use WSL, you can run Ubuntu on Windows almost natively,
furthermore, you can directly invoke Windows .exe files from Ubuntu.
In this chapter, we will examine the workings and configuration of WSL, and the execution steps for .exe in detail.

7.1 What is WSL? — “Ubuntu Inside Windows”

WSL (Windows Subsystem for Linux) is a mechanism to run Linux on Windows developed by Microsoft.
Unlike traditional virtual machines, a portion of the Windows kernel provides Linux kernel compatibility features, and
lightweight, high‑performance execution of Linux commands and applications is its hallmark.

Currently, WSL 2 is the mainstream version, and because it operates using a real Linux kernel,
performance and compatibility have significantly improved.

7.2 Installing Ubuntu and Initial Setup (WSL 2)

① Enable WSL

Run PowerShell as “Run as administrator” and enter the following command.

wsl --install

This will automatically install WSL 2 and Ubuntu.
If you already have WSL 1 installed, upgrade with the following command.

wsl --set-default-version 2

② Launch Ubuntu

After installation, “Ubuntu” will appear in the Start menu.
When you set a username and password on first launch, you’re all set.

7.3 Running Windows .exe from Ubuntu

A major advantage of the WSL environment is that you can directly invoke Windows apps from Ubuntu.
For example, entering the following launches Windows “Notepad”.

notepad.exe

Similarly, Windows apps can be invoked simply by adding .exe.

explorer.exe .
calc.exe
cmd.exe

As shown above, you can open File Explorer, Calculator, and other native Windows apps from the Ubuntu terminal.

File sharing is also seamless

From Ubuntu in WSL, the Windows file system can be accessed via paths such as /mnt/c/.

cd /mnt/c/Users/YourName/Downloads wine.exe app.exe

It is also possible to combine Ubuntu commands with Windows apps.
For example, you can open a file downloaded in Ubuntu with a Windows application,
taking advantage of both environments at once.

7.4 Operating Ubuntu from the Windows Side

The reverse direction is also possible.
You can call Ubuntu commands from Windows PowerShell or Command Prompt.

wsl ls -la wsl python3 script.py

This enables you to call Linux commands directly from a Windows development environment, making
integration of development and testing environments very smooth.

7.5 Limitations in the WSL Environment

7.6 Examples of Use in Development

WSL is not just a plain Ubuntu environment; it is also an excellent
development environment that moves between Windows and Linux.

Example 1: VS Code + Ubuntu

If you use Visual Studio Code’s “Remote – WSL” extension,
you can edit and run files inside Ubuntu from VS Code on Windows.

Example 2: Docker on WSL 2

In WSL 2, Docker Desktop is natively integrated.
This enables Linux containers to run directly on Windows.

Example 3: Integration of Linux tools + Windows apps

ffmpeg, grep, awk while leveraging Linux commands,
you can also flexibly perform the final processing with Windows applications.

7.7 Summary of WSL Benefits and Drawbacks

7.8 Summary

WSL is the easiest way for Windows users to “install Ubuntu”.
And the ability to directly execute .exe from Ubuntu makes a
“cross‑platform” hybrid development environment that bridges Windows and Linux possible.

However, this is a method for running Ubuntu on Windows, not for running .exe directly on Ubuntu itself.
It is important to consider which workflow aligns with your style when choosing.

8. Example: Results of Actually Running .exe on Ubuntu

So far, we have introduced methods for running .exe on Ubuntu.
Here, we organize the results of actually running several representative Windows applications in an Ubuntu environment.
From a practical perspective such as “Which method works?” and “What errors appear?”, we will look at both successful and failed cases.

8.1 Overview of Test Environment

• OS：Ubuntu 22.04 LTS（64bit）
• CPU：Intel Core i7
• Memory
• Graphics
• Wine：WineHQ Stable 9.x
• Virtual environment
• WSL environment

8.2 Successful Cases (Smooth Operation)

① Notepad++ (Text Editor)

• Method
• Result
• Supplement
• Comment

wine notepad++.exe

✅ Startup time: about 3 seconds
✅ No issues with saving settings or plugin operation.

② 7-Zip (Compression/Decompression Tool)

• Method
• Result
• Supplement

Practical rating: ★★★★★ (Stable operation)

③ Paint.NET (Image Editing Software)

• Methoddotnet40
• Result
• Points to note

Practical rating: ★★★★☆ (Requires configuration but runs stably)

8.3 Cases that Worked Under Conditions (Stable Depending on Settings)

① Excel Viewer (Microsoft-made)

• Methodvcrun2015msxml6
• Result
• Cause

Practical rating: ★★★☆☆

② RPG Tsukūru-made game

• Method
• Result
• Causewinetricks d3dx9
• Notes

Practical rating: ★★☆☆☆ (Acceptable for lightweight 2D)

③ LINE (Windows version)

• Methodcorefontsvcrun6
• Result
• Noteshttps://line.me/

Practical rating: ★★★☆☆ (Suitable for experimental use)

8.4 Cases That Did Not Work (Difficult with Wine)

① Adobe Photoshop / Illustrator (CS and later)

• Method
• Result
• Cause
• Alternative solution

Practical rating: ★☆☆☆☆ (Unrealistic with Wine)

② Ichitarō / Fudemame and other Japanese-specialized software

• Method
• Result
• Reason
• Alternative solution

Practical rating: ★☆☆☆☆

③ 3D games and CAD-type apps (e.g., AutoCAD, Skyrim)

• Method
• Result
• Reason
• Alternative solution

Practical rating: ★☆☆☆☆ (Requires virtualization)

8.5 Summary: Practical Decision Criteria

8.6 Lessons Learned from the Field

• Choosing an app that has been verified to work is more realistic than running it with Wine.
• Apps that won’t run can be switched immediately with 「virtualization or WSL」.
• Just resolving runtime dependencies (.NET, VC++) significantly improves performance.
• Japanese fonts and input systems have the most trouble in Wine.

8.7 Summary

Running .exe on Ubuntu is not universal but sufficiently practical.
Especially lightweight apps and development support tools run without issues, and
the “scope of work that can be done without Windows” is expanding year by year.

On the other hand, for business software and GPU-dependent apps,
using a virtual machine or a Windows environment in conjunction is the optimal solution.
In other words, choosing between “Wine”, “virtualization”, and “WSL” according to the purpose leads to the most efficient and stable operation.

9. Troubleshooting and Common Error Solutions

When you try to run a .exe on Ubuntu, you will almost always encounter some error at first.
Issues such as “won’t start”, “garbled text”, or “installer stops midway” are not uncommon, especially troubles specific to Wine or virtualization environments.

In this section, we systematically organize the causes and solutions for common troubles.
We have compiled remedies by symptom, so please check the ones that apply to your environment in order.

9.1 “Cannot execute binary file” is displayed

Symptoms

bash: ./program.exe: cannot execute binary file: Exec format error

Cause

You are running the .exe directly without going through Wine, or Wine is not installed.

Solution

sudo apt install wine64 wine32
wine program.exe

Or, right-click the .exe file and select “Open with Wine”.

Note: If you type file program.exe, information such as PE32 executable will be displayed.
If this appears, it is evidence that the file format cannot be executed directly on Ubuntu.

9.2 “Missing DLL” error

Symptoms

When launching the app, the following message appears:

“msvcr100.dll is missing”
“d3dx9_43.dll not found”

Cause

Dependent libraries such as Windows runtimes or DirectX are missing.

Solution

winetricks to install the missing libraries.

sudo apt install winetricks
winetricks vcrun2015
winetricks d3dx9
winetricks dotnet40

If you want to reset the Wine environment, you can rebuild it as follows:

rm -rf ~/.wine
winecfg

9.3 Garbled text / Font issues

Cause

Wine is configured primarily with English fonts, so fonts needed for Japanese display are missing.

Solution

1. Add Japanese font:
2. Or copy Windows fonts:

Notes

winetricks allfonts can be run to install all fonts at once.

9.4 Japanese input (IME) not working

Cause

The Wine environment does not support Japanese IME by default.

Solution

• fcitxibus
• Alternatively, temporarily input text using an Ubuntu native app (e.g., gedit), and paste it on the Wine side.

Alternative

If the software requires input functionality, using a virtual machine environment is more reliable.

9.5 Screen stays black / freezes even after launch

Cause

DirectX or OpenGL drivers are not properly configured, or the GPU driver is unsupported.

Solution

• Reinstall NVIDIA/AMD drivers from official repository:
• Enable ‘Graphics Driver Emulation’ in Wine settings:
• For 3D apps, should be installed.

9.6 Application stops during installation

Cause

The installer requires specific Windows APIs (e.g., MSXML, IE runtime, etc.).

Solution

Recreate a clean Wine virtual environment or install dependent DLLs individually:

winetricks msxml6 corefonts ie8

Alternatively, trying the installation on a virtual machine is also effective.

9.7 “File path not found” or “Access denied”

Cause

Ubuntu cannot interpret Windows-style paths (e.g., C:Program Files...), or there is insufficient permission.

Solution

• Enclose the path in :
• Grant execution permission:

Caution

sudo can corrupt the Wine environment. Always run it with regular user privileges.

9.8 “Sound device not available” (no sound)

Cause

PulseAudio settings conflict with Wine.

Solution

Open the Wine configuration tool and re-select “PulseAudio” or “ALSA” on the [Audio] tab.

winecfg → [Audio] → Re-detect devices

If playback is unstable, install pavucontrol and explicitly set the output device.

9.9 Unable to use USB devices or printing in VirtualBox

Cause

The extension pack is not installed, or the user is not a member of the vboxusers group.

Solution

sudo apt install virtualbox-ext-pack
sudo usermod -aG vboxusers $USER

After that, log out and log back in, then try again.

9.10 When you want to reset the entire Wine setup

If the environment is broken or the settings are a mess, you can reset it as follows.

rm -rf ~/.wine
winecfg

This will generate a new virtual C: drive and return you to a clean environment.

9.11 Troubleshooting checklist (summary)

9.12 Summary

Many of the problems you encounter when running a .exe on Ubuntu are caused by insufficient Wine environment configuration or missing dependent libraries.
The basic approach is to calmly address them step by step using the following procedures.

1. First (which DLL or API is the cause?)
2. Supplement missing libraries with winetricks
3. If you don’t improve,

If you understand these, running a .exe on Ubuntu becomes much more stable, and even beginners will be able to resolve troubles on their own.

10. Alternative: Replacing Windows software with Linux-native apps

There are many ways to run .exe on Ubuntu, and there are also many cases where
“using an equivalent Linux-compatible app is more stable and comfortable than the effort to make it run”

In this section, we introduce practical alternatives for replacing Windows apps with Linux-native apps.
We provide a list of apps selectable by purpose and also explain migration tips and cautions.

10.1 “Replacement” is a standard strategy for Ubuntu users

Running .exe with Wine or a virtual machine is possible, but

• Bugs (fonts and input-related) are likely to occur
• It takes effort to maintain updates and compatibility
• It may compromise system stability

There are disadvantages such as that.

On the other hand, Linux-oriented open-source and cross-platform apps are
feature and usability roughly equivalent to or better than the Windows version, and
switching is a realistic option in many areas.

10.2 Commonly Used Alternative Apps List

🧾 Office & Document Creation

🧠 Programming & Development

🎨 Image & Video Editing

🎧 Music & Multimedia

🌐 Web & Networking

10.3 Cases Where Migration Is Relatively Easy in Practice

The following categories transition to Ubuntu relatively smoothly.

On the other hand, many CAD, accounting, and custom business software such as industry-specific applications are Windows-based, and
using them in conjunction with virtual machine operation is realistic.

10.4 Tips for Introducing Linux-native Apps

1. Using Snap and FlatpakIn Ubuntu, in addition to the conventional APT, you can easily obtain the latest apps with “Snap” or “Flatpak”. sudo snap install krita sudo flatpak install flathub org.libreoffice.LibreOffice
2. Customize Settings and ShortcutsMany Linux apps allow changing keyboard shortcuts and themes, so it’s possible to make the operation feel like Windows.
3. Check data format compatibilityExample: Office documents are , verify compatibility. GIMP can open but recognize that it is not a full recreation.

10.5 Benefits of Going Linux-native

10.6 Summary: Shifting Mindset for Comfortable Work on Ubuntu

.exe is certainly convenient, but if you plan to use Ubuntu long-term,
“Optimizing for Linux rather than recreating Windows” is the ideal direction.

• First
• If it doesn’t work properly,
• In the long term, will be advanced.

By thinking in this three-step way, you can build a stable environment without strain.
Ubuntu’s software ecosystem is extremely rich, and once you get accustomed, you will often find that the need to run
“.exe” becomes almost unnecessary.

11. Summary: Optimal Choices and Decision Criteria for Handling .exe on Ubuntu

So far, we have covered every method for running .exe files on Ubuntu.
Wine, virtual machines, WSL, and even migration to Linux native applications each have their own strengths and limitations.

In this section, we summarize them and organize “which method to choose” by purpose and environment.
Finally, we compile a way of thinking for Ubuntu users to work smoothly with .exe.

11.1 Reorganizing the Four Options for Running .exe on Ubuntu

11.2 Recommended Approaches by Use Case

11.3 Common Misconceptions and Cautions

❌ “If you install Wine, everything works”

→ More precisely, “only some applications work”. Wine is not a cure‑all, and
checking compatibility reports on AppDB (the official WineHQ database) is essential.

❌ “Virtual machines are fast”

→ Virtualization is stable, but it incurs higher CPU and memory load than native.
Adequate specs are required for long‑running or heavy workloads.

❌ “Linux Office suites are perfectly compatible”

→ LibreOffice and similar suites are highly compatible, but macros or certain layouts may break.
Always test business documents.

✅ “Once you get used to native apps, you won’t want to go back”

→ Once you build a workflow optimized for the Linux environment,
it becomes overwhelmingly comfortable in terms of updates, security, and performance.

11.4 Three‑Step Strategy to Reduce Troubles

1. First, try with Wine　→ If it’s a lightweight app or a standalone executable, this is sufficient.　If it fails, move on to the next step.
2. If it doesn’t run, switch to a virtual machine　→ 100% operation is required for business applications or driver-dependent software, this is the place.
3. In the long term, transition to a Linux native app　→ It is the most realistic in terms of maintainability, stability, and security.

By being aware of these three stages,
you can minimize troubles like “doesn’t run” or “settings broken”.

11.5 How Ubuntu Users Should Relate to .exe

Ubuntu is not merely a “Windows replacement”;
it is a powerful OS with its own ecosystem.

.exe chasing is a “transitional option”, and
ultimately the ideal is to aim for a configuration that can be completed in a native Ubuntu environment.

In short:

• Wine and virtualization are and not permanent dependencies.
• The purpose is not “to reproduce Windows”, but “to make the most of Ubuntu”.
• Rather than just being able to run , the essence is

11.6 For Those Starting Work on Ubuntu

1. Try without fear
2. Build Simply
3. Record troubles
4. Review regularly
5. Learn Linux Native

11.7 Conclusion: Ubuntu × exe = “Choice and Differentiated Use”

The optimal way to handle .exe on Ubuntu is, varies according to purpose and use case.

• If you want to try it simply →
• If stability is important →
• If you want to have both development environments →
• If you are thinking about long-term operation →

The important thing is the flexibility to not cling to a single solution but to choose the optimal answer for each purpose. That is the smartest way to leverage Ubuntu.

12. FAQ (Frequently Asked Questions)

When you try to run .exe on Ubuntu, many beginners encounter the same questions and troubles.
In this section, we have compiled frequently asked questions from real users,
and provided clear answers for each.
Use this as the final touch to deepen your understanding of the whole article.

Q1. Why can’t I open .exe files directly on Ubuntu?

.exe is Windows-only executable format (PE format), and Ubuntu (Linux) uses ELF format.
In other words, because the file structure and internal APIs are completely different, Ubuntu’s kernel cannot recognize .exe as an executable program.

→ Solution: You need to execute it via Wine, e.g., wine your_app.exe.

Q2. Does every .exe run when using Wine?

No. Wine is not all‑powerful.
While Wine reproduces Windows APIs, it is not a complete emulation, so some apps may be unstable or fail to launch.

→ Workaround:

• WineHQ AppDB
• winetricksvcrun2015dotnet40
• If it still doesn’t work, running the entire Windows on a is the sure way.

Q3. Nothing happens when I double‑click .exe. What should I do?

Ubuntu determines programs by execution permission rather than file extension.
Also, if Wine is not associated, it will not run.

→ Workaround:

chmod +x setup.exe
wine setup.exe

Or right‑click in the file manager → select “Open with Wine”.

Q4. Japanese text is garbled in Wine. How can I fix it?

Wine uses English fonts by default, so Japanese fonts are missing.

→ Workaround:

sudo apt install fonts-noto-cjk

Alternatively, copy meiryo.ttc or msgothic.ttc from Windows C:WindowsFonts to ~/.wine/drive_c/windows/Fonts/.
This make Japanese apps display correctly.

Q5. When I try to open .exe, I get “Cannot execute binary file”.

This is an error because Ubuntu does not treat .exe as an executable format.
Wine may not be installed, or 32‑bit support may be disabled.

→ Workaround:

sudo dpkg --add-architecture i386
sudo apt update
sudo apt install wine64 wine32

After that, try wine your_app.exe again.

Q6. Can I run .exe from Ubuntu on WSL?

Yes, it is possible.
Because WSL (Windows Subsystem for Linux) integrates with the Windows kernel,
you can launch Windows apps directly from Ubuntu.

notepad.exe
explorer.exe .

In this way, calling .exe from the Ubuntu terminal launches the corresponding Windows application.
However, it is impossible on pure Ubuntu alone.

Q7. Can games run on Wine?

Lightweight 2D games and older titles may work.
However, 3D games that heavily use DirectX or recent titles are unstable.

→ Countermeasure:

• winetricks d3dx9vulkan
• Use the compatibility layer “Proton (Steam compatibility version of Wine)”

In Steam’s Proton environment, many Windows games can run on Ubuntu.

Q8. An app crashes in Wine. Is reinstalling the only option?

In many cases, resetting Wine’s virtual environment resolves the issue.

rm -rf ~/.wine
winecfg

This returns you to a clean environment, allowing reconfiguration without reinstalling.
However, application data will also be deleted, so back up any needed files beforehand.

Q9. Should I use Wine or a virtual machine?

Conclusion:
If you want a quick test, use Wine; if you need guaranteed operation, use a virtual machine is the principle.

Q10. I want to switch to Linux‑compatible apps, where can I find them?

The following methods are recommended:

• Ubuntu Software Center (GUI)
• Command line:
• Website:

In particular, LibreOffice, GIMP, VS Code, Kdenlive, Inkscape are standard options, and
they are representative examples that are easy to migrate from Windows apps.

Q11. Is it secure to run Windows apps on Ubuntu?

When running .exe with Wine, there is a possibility of launching Windows malware.
Ubuntu itself is less prone to virus impact, but the Wine environment, as a Windows compatibility layer, carries infection risk.

→ Security measures:

• Obtain only from trusted sites
• ~/.wine
• Store important data separately from the Wine environment.

Q12. In the end, which method is most recommended?

It depends on the use case.
However, the following priority order is the most efficient:

1. Wine
2. If it doesn’t work properly, migrate to
3. If you prioritize long-term operation and stability, replace with

If you follow this flow, you can minimize the stress of using .exe on Ubuntu.

Q13. Is handling .exe on Ubuntu difficult?

It takes a little getting used to at first, but once you understand the basic operations (install, run, delete) it isn’t difficult.
In fact, it’s a great chance to learn how Linux works through Ubuntu.
Once you grasp the mechanism, you can build a more flexible and stable work environment than Windows.

Q14. Will Wine and virtualization become unnecessary in the future?

They won’t disappear completely, but
many software are moving toward cross‑platform (Windows/Linux) support.
Especially with the shift to web apps and cloud, “.exe‑independent” environments are definitely expanding.

Q15. What is the recommended first step for Ubuntu beginners?

• wine notepad.exe
• LibreOffice and GIMP, etc.,
• And determine what only runs on Windows.

The best approach is to try small things and gradually get accustomed to Ubuntu.
Take it step by step without rushing.

Summary

There are many ways to run .exe on Ubuntu, but the important point is that there is no single “right” answer.
Wine, virtualization, WSL, and native migration—by using these appropriately,
you develop an engineering mindset that can flexibly handle any environment.

“Not just ‘run’ but ‘understand and choose’”
That is the first step toward true freedom for Ubuntu users.