How to Run .exe Files on Ubuntu: Complete Guide to Wine, Virtual Machines, and WSL

1. Introduction — Why There Is a Need to Run .exe Files on Ubuntu and the Purpose of This Article

When migrating from Windows to Ubuntu, it is not uncommon to encounter situations where you still depend on indispensable business software, small utilities, or games that rely on .exe files (Windows executable files). However, because Ubuntu (Linux) uses a different execution format and system architecture from Windows, you cannot simply double-click a .exe file and run it directly.
The purpose of this article is to organize practical options for answering the real-world question of “How can .exe files be handled on Ubuntu?”, and to help readers choose the most suitable method based on their environment and objectives.

Key Points of This Article

• .exe files are Windows-specific executables (PE format) and are not compatible with Ubuntu’s standard executable format (ELF).
• Based on that premise, the main approaches for handling .exe files on Ubuntu can be broadly categorized into the following three methods:
  • Using Wine: Running .exe files by recreating and translating Windows APIs on Ubuntu
  • Virtualization or emulation: Running Windows itself as a guest OS using tools such as VirtualBox, then executing .exe files inside it
  • Using WSL (Windows-based environments): A special case where .exe files are handled from Ubuntu running on Windows
• Each approach has its strengths and weaknesses. In practice, Wine works well for lightweight utilities, virtual machines are best for maximum compatibility, and WSL-based workflows are effective when a Windows host is available.

Goals of This Article

• Enable readers to understand the recommended order to try solutions and alternative approaches, based on their requirements (target software, performance and stability priorities, setup effort, licensing, and cost).
• Allow readers to reproduce actual execution procedures (especially using Wine) and handle common troubleshooting points when applications do not work as expected.
• Help readers recognize Linux-native alternatives as a viable “different solution” when sticking to .exe files is unnecessary.

Intended Audience

• Beginner to intermediate Ubuntu users who want to run specific Windows applications on Ubuntu
• Users who want to choose the most appropriate method depending on their needs, from “just trying it out” to “stable operation for business use”
• Those who have already tried Wine or virtualization but are struggling with errors or instability

Suggested Reading Flow

1. Basic understanding (Differences between .exe files and Ubuntu)
2. Overview of available methods (Comparison of Wine, virtualization, and WSL)
3. Practical steps (Installing and running Wine, key configuration points)
4. Troubleshooting (Common issues and checklists)
5. Alternatives (Linux-native and cross-platform applications)
6. Final decision guidance (Which method to choose and what to try next)

Important Notes Before You Begin

• Not all .exe files behave the same way. Behavior varies depending on application-specific implementations, required DLLs, 32-bit vs 64-bit architecture, and graphics or driver dependencies.
• Although this article presents generally applicable and reproducible steps, it does not guarantee full compatibility for every application. Alternative solutions are also provided for cases where things do not work.
• When using these methods in corporate or organizational environments, be sure to check software licenses and security policies.

2. What Is an .exe File? — Fundamentals of Windows Executable Formats

Before diving into how .exe files can be handled on Ubuntu (Linux), it is important to understand what .exe files (and Windows executable formats in general) actually are, and why they differ from Linux executables.

2.1 What Are .exe Files and the PE Format?

Overview of the PE (Portable Executable) Format

• On Windows, executable files (.exe), libraries (.dll), and device drivers all use the PE (Portable Executable) format.
• The PE format is an extension of the older COFF (Common Object File Format) and contains all the information required by the Windows loader, such as imports and exports, section layouts, and header data.
• A typical .exe file consists of an MS-DOS header, a DOS stub, a PE header, and multiple sections. The DOS stub exists for backward compatibility and displays messages like “This program cannot be run in DOS mode.”

Main Structural Components (Simplified)

As shown above, the PE format includes not only the program itself, but also extensive metadata and linkage information required for execution on Windows.

2.2 Linux (Ubuntu) Executable Format: Characteristics of ELF

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

The ELF format is widely used across UNIX-like systems and is designed with portability and flexibility in mind. Its main characteristics include the following:

• Supports multiple use cases such as executable binaries, shared libraries, and object files
• Consists of headers, segments and sections, symbol tables, and relocation information
• Uses a dynamic linker (such as ld.so) to resolve libraries at runtime
• The Linux kernel and loader mechanisms are fundamentally designed around the ELF format

ELF works naturally with Linux execution environments, and standard tools such as readelf, objdump, and ldd can be used to inspect and analyze ELF binaries.

2.3 Differences Between PE and ELF — Why .exe Files Cannot Run Natively on Ubuntu

The Windows PE format and the Linux ELF format differ at a fundamental design level. These differences are the core reason why .exe files cannot be executed directly on Ubuntu.

Key Differences and Compatibility Barriers

Discussions within developer communities consistently emphasize that PE and ELF are “formats designed for the same purpose but not mutually readable.” Attempts to convert ELF binaries into PE executables have shown that non-trivial native applications cannot be made binary-compatible, primarily due to differences in system calls and runtime environments.

2.4 Why the System Reports “Cannot Execute” Errors

• Double-clicking a .exe file on Ubuntu often results in errors such as “not an ELF executable” or “invalid executable format”
• Running the file command on a .exe file typically outputs something like “PE32 executable,” explicitly indicating it is not a Linux executable
• .exe files are designed exclusively for Windows environments and do not meet Linux loader requirements

3. Why .exe Files Cannot Be Executed Directly on Ubuntu

In the previous section, we confirmed that .exe files are Windows-specific executables based on the PE format.
This section explains how those structural differences translate into practical limitations that prevent .exe files from running directly on Ubuntu.

3.1 “Execution” on Ubuntu and Windows Are Fundamentally Different

On Linux-based systems such as Ubuntu, the program execution mechanism (execution loader) is fundamentally different from that of Windows.
Even though the action of “double-clicking a file to run it” appears similar, the underlying processes are entirely different.

How Execution Works on Windows

• The OS kernel analyzes the PE header and loads required DLLs (dynamic libraries).
• Applications operate through layered Windows APIs such as ntdll.dll, kernel32.dll, and user32.dll.
• GUI applications render via the Windows window manager and handle user interactions like mouse clicks and keyboard input.

How Execution Works on Ubuntu (Linux)

• Executable files must be in ELF format, which the Linux kernel can parse and load.
• Shared libraries (.so) are dynamically linked, and applications rely on POSIX-compliant system calls such as open, read, fork, and execve.
• Because file formats and APIs differ, PE-format .exe files cannot be recognized and are rejected as non-executable.

As a result, when Ubuntu encounters a .exe file, it treats it as an unknown structure and refuses to execute it.

3.2 Example Error Messages

If you attempt to double-click a .exe file or run it from the terminal using ./program.exe, you may see an error like the following:

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

This error does not indicate a corrupted file. Instead, it means that Ubuntu does not know how to execute this file format.

3.3 The Absence of Windows APIs

The most fundamental reason .exe files cannot run on Ubuntu is that Windows APIs do not exist in Linux environments.

.exe files internally call Windows-specific functions such as:

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

These functions belong to Windows-specific libraries like kernel32.dll and user32.dll.
Because Ubuntu does not provide these APIs, even if the file format were readable, there would be no target implementation to execute the calls.

3.4 Differences in Filesystems and Environment Variables

Windows and Ubuntu differ significantly in filesystem structures and environment variable conventions.

Windows applications often assume the existence of drive letters such as C:\. Because Ubuntu does not use this model, file paths referenced internally by Windows programs frequently fail.

3.5 DLL Dependencies and Compatibility Issues

Many .exe files appear to be standalone, but in reality they depend on multiple DLLs (dynamic-link libraries).
Examples include d3d9.dll for graphics, dsound.dll for audio, and ws2_32.dll for networking.

Ubuntu does not provide these DLLs or the Windows API implementations behind them.
As a result, execution fails when the application attempts to load or call these libraries.

3.6 CPU Instruction Sets Are Similar, but OS Architecture Still Matters

Modern Ubuntu and Windows systems often run on the same x86_64 (AMD64) architecture, meaning CPU instruction sets are largely compatible.
However, differences in OS-level execution environments—such as system calls and memory management—prevent applications from running across platforms.

This is especially relevant when attempting to run 32-bit Windows executables on 64-bit Ubuntu systems without a compatibility layer like Wine.

3.7 Summary: The Issue Is Not a Technical Limitation but a Design Difference

The inability to run .exe files natively on Ubuntu is not due to a lack of capability, but rather to fundamentally different OS design philosophies.

• Different file formats (PE vs ELF)
• Different APIs (Windows API vs POSIX/Linux system calls)
• Different dynamic library systems (DLL vs .so)
• Different path, permission, and environment models
• Different loader mechanisms

Therefore, running .exe files on Ubuntu requires introducing an intermediate compatibility layer that bridges these differences.
This role is fulfilled by tools such as Wine and virtualization software, which are explained in the next section.

4. Three Ways to Run .exe Files on Ubuntu

So far, we have explained why Ubuntu cannot execute Windows .exe files natively.
However, running them is not impossible.
By using appropriate compatibility layers or virtual environments, many Windows applications can be executed on Ubuntu.

This section introduces the three most common methods for running .exe files on Ubuntu.
By comparing their characteristics, advantages, and disadvantages, you can determine which approach best fits your use case.

4.1 Using Wine (The Most Lightweight Compatibility Layer)

What Is Wine?

Wine (Wine Is Not an Emulator) is, as its name suggests, not an emulator but a compatibility layer that re-implements Windows APIs on Linux.
Instead of running a full Windows OS, Wine translates Windows API calls into Linux system calls.

Because Wine does not rely on virtualization or CPU emulation, it is generally lighter and faster than running Windows in a virtual machine.

Wine has been under active development for over 20 years and can be easily installed via Ubuntu’s official repositories or WineHQ’s PPA.
For users who prefer a graphical interface, tools such as PlayOnLinux or Bottles provide user-friendly frontends.

Installation Steps (Ubuntu 22.04 / 24.04)

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

If you want the latest stable version, you can 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

Alternatively, you can right-click a .exe file in the file manager and select “Open with Wine.”
On first launch, Wine creates the ~/.wine directory, which contains a virtual Windows-like C drive structure.

Advantages

• Lightweight and fast (significantly less resource usage than virtual machines)
• Many Windows applications, especially older ones, work well
• Easy file sharing between Ubuntu and Windows applications

Disadvantages

• Not all applications are supported (compatibility varies by application)
• Games and 3D applications may be unstable
• 32-bit and 64-bit mixed environments can cause issues

Practical Tip

You can check application compatibility in the official WineHQ AppDB.
Applications are rated as Platinum, Gold, Silver, Bronze, or Garbage based on reported compatibility.

4.2 Using Virtual Machines or Emulators (Maximum Stability)

If Wine does not work well or you need guaranteed stability for business use, virtual machines are the most reliable option.
Common solutions include VirtualBox, VMware Workstation, and QEMU/KVM.

How It Works

A virtual machine creates a virtual hardware environment on Ubuntu and runs a full Windows OS as a guest system.
In other words, you are running an entire Windows PC inside Ubuntu.

High-Level Setup Steps

1. Install VirtualBox or a similar tool
   sudo apt install virtualbox
2. Download a Windows ISO image from Microsoft
3. Create a virtual machine and install Windows from the ISO
4. Run .exe files normally inside the Windows guest OS

Advantages

• Extremely high compatibility (almost everything that runs on Windows will work)
• Stable and predictable behavior
• Easy management of networking, file sharing, and snapshots

Disadvantages

• High resource usage (CPU, memory, and storage)
• Requires a valid Windows license
• Slower startup time compared to Wine

Recommended Use Cases

• Business or accounting software that must run reliably
• 3D applications or software requiring specialized drivers
• Windows development or testing environments

4.3 Using WSL (Windows Subsystem for Linux): A Reverse Approach

The final method takes a different perspective.
If you are running Ubuntu inside Windows, you can use WSL (Windows Subsystem for Linux) to work with .exe files.

How WSL Works

Ubuntu running under WSL is actually a Linux environment hosted on Windows.
As a result, you can directly invoke Windows executables from the Ubuntu terminal.

notepad.exe

This command launches Windows Notepad directly from Ubuntu.
Because WSL shares the Windows kernel, Windows executables can be called natively.

Advantages

• Run Windows .exe files without additional setup
• Seamless file sharing between Linux and Windows environments
• Excellent integration with development tools such as VS Code and Docker

Disadvantages

• Only works when Ubuntu is running on Windows (WSL environment)
• Some GUI applications and hardware interactions are limited
• Not applicable to standalone Ubuntu systems

4.4 Which Method Should You Choose? (Comparison Table)

4.5 Summary

The best way to run .exe files on Ubuntu depends on how much compatibility and performance you require.

• Ease of use and speed → Wine
• Stability and full compatibility → Virtual Machines
• Windows-centric workflows → WSL

Understanding these options allows you to select the most suitable approach for your environment and goals.

5. Step-by-Step Guide to Running .exe Files with Wine (Ubuntu-Compatible)

This section provides a detailed, practical guide to using Wine, the most accessible way to run .exe files on Ubuntu.
To ensure clarity for first-time users, the steps are explained from installation and initial setup to execution and troubleshooting.

5.1 What Wine Is — A “Translation Layer” for Windows Applications

Wine stands for “Wine Is Not an Emulator.” It is a compatibility layer that re-implements Windows APIs on Linux.
Rather than emulating Windows itself, Wine translates Windows API calls into Linux-compatible system calls.

The key advantage is that Wine runs directly on the Linux kernel, rather than simulating an entire operating system.
This allows for significantly lower resource usage and faster execution compared to virtual machines.

5.2 Installing Wine (Ubuntu 22.04 / 24.04)

First, install Wine to prepare the execution environment.
While Wine is available in the default Ubuntu repositories, using the official WineHQ repository ensures access to the latest stable version.

① Enable 32-bit Architecture Support

sudo dpkg --add-architecture i386

Many Windows applications are still 32-bit, so enabling 32-bit support is recommended even on 64-bit systems.

② 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

③ Install Wine

sudo apt install --install-recommends winehq-stable

④ Verify the Installation

wine --version

If a version such as wine-9.x is displayed, the installation is complete.

5.3 Initial Configuration (First Launch)

When using Wine for the first time, run the configuration tool:

winecfg

This creates the ~/.wine directory and sets up a virtual Windows-style drive structure.

The directory layout typically looks like this:

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

Wine recreates a Windows-like filesystem inside this directory and installs applications there.

5.4 Running an .exe File

Method 1: From the Command Line

wine ~/Downloads/setup.exe

Method 2: From the File Manager

Right-click the .exe file and select “Open with Wine.”
Both methods work identically.

If the file is an installer, a familiar Windows-style setup wizard will appear.
Once installed (typically under C:\Program Files), the application can be launched as follows:

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

5.5 Fixing Japanese Text Rendering Issues

English applications usually work without issues, but Japanese applications may display garbled text.
To resolve this, install Japanese fonts on Ubuntu.

sudo apt install fonts-noto-cjk

Alternatively, you can copy font files such as msgothic.ttc or meiryo.ttc from a Windows system into:

~/.wine/drive_c/windows/Fonts

This often resolves character rendering problems.

5.6 Using Winetricks (Helpful Auxiliary Tool)

winetricks is a helper script that makes it easy to install additional components such as DLLs, fonts, and runtime libraries.

Install Winetricks

sudo apt install winetricks

Example: Installing Visual C++ Runtime

winetricks vcrun2015

This resolves many common “DLL not found” errors.

5.7 Checking Compatibility with WineHQ AppDB

Wine provides an official compatibility database called WineHQ AppDB.
Each application is assigned a rating based on real-world test results:

Searching for your application name often reveals recommended settings and workarounds.

5.8 Common Errors and Solutions

5.9 Examples of Applications That Run Well with Wine

5.10 Summary

Wine is one of the most practical ways to run .exe files on Ubuntu.
It strikes a good balance between lightweight performance, compatibility, and ease of setup.

Because compatibility varies by application, it is recommended to check AppDB in advance and use Winetricks when needed.

6. Using Virtual Machines, Emulators, and Containers

While Wine can run many Windows applications, it does not guarantee perfect compatibility in all cases.
In particular, business software, accounting applications, games with 3D rendering, and applications that rely on device drivers often behave unstably or fail to start under Wine.
In such situations, using virtual machines, emulators, or containers becomes an effective solution.

This section explains how each approach works and how they can be used in practice to run .exe files on Ubuntu.

6.1 What Is a Virtual Machine? — “Running a Full Windows System Inside Ubuntu”

A virtual machine (VM) recreates virtual PC hardware on Ubuntu and runs Windows as a complete guest operating system.
Representative solutions include the following:

• VirtualBox (free and open source)
• VMware Workstation Player (free for non-commercial use)
• QEMU / KVM (high-performance, Linux-native virtualization)

Conceptual Overview

[Ubuntu Host OS]
 ├── Virtual Machine Software
 │     ├── Virtual CPU / Memory / Disk
 │     └── [Windows Guest OS]
 │            └── .exe Execution

This approach installs and runs a real Windows OS inside Ubuntu.
Because no API translation is required, it offers near-complete compatibility.

6.2 Running Windows with VirtualBox

① Install VirtualBox

sudo apt update
sudo apt install virtualbox

② Prepare a Windows ISO Image

Download a Windows 10 or Windows 11 ISO image from Microsoft’s official website.
Activation can be completed later, as Windows will still run during the evaluation period.

③ Create a Virtual Machine

1. Launch VirtualBox and click “New”
2. Set a name (for example, Windows11)
3. Type: Windows / Version: Windows 11 (64-bit)
4. Allocate at least 2 GB of memory and 40 GB of disk space

④ Mount the ISO and Install Windows

Select the created VM, then open:
[Settings] → [Storage] → [Optical Drive], and attach the downloaded ISO file.

Start the VM and follow the standard Windows installation process.

⑤ Running .exe Files

Once Windows is running, .exe files can be executed normally.
To exchange files between Ubuntu and Windows, configure shared folders in VirtualBox.

6.3 Using VMware Workstation Player

VMware is often faster and more stable than VirtualBox, making it popular for professional use.
On Ubuntu, it can be installed by downloading a .bundle installer from the official website.

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

The GUI installer launches and guides you through the setup.

Advantages

• Strong GPU virtualization support, suitable for 3D applications
• Robust support for networking and USB devices

Disadvantages

• High system resource consumption
• Commercial use requires a paid license

6.4 Using QEMU / KVM (Advanced Users)

QEMU and KVM are virtualization technologies built directly into Linux.
They are well-suited for automation, development, and testing environments.

Installation

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

GUI Management

Launching virt-manager provides a graphical interface similar to VirtualBox.

Key Characteristics

• Near-native performance
• Powerful command-line tools such as virsh and qemu-system-x86_64
• Flexible virtual networking and snapshot management

6.5 Using Containers as a Lightweight Alternative

As a lighter alternative to full virtual machines, containers can be used.
One example is running Wine inside a Docker container.

Although this does not provide full virtualization, containerized Wine environments improve reproducibility and isolation.

Example: Running Wine in a Docker Container

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

Inside the container, you can run:

wine /data/app.exe

Advantages

• No impact on the host system
• Easy to share configurations with other users
• Suitable for automation and CI/CD workflows

Disadvantages

• GUI configuration can be complex (X11 forwarding required)
• Limited audio and 3D acceleration support

6.6 Comparison of Methods

6.7 Which Option Should You Choose?

Recommendations by purpose:

6.8 Summary

Virtual machines and emulators consume more system resources than Wine, but they offer far superior compatibility and stability.
For business-critical software or driver-dependent applications, running a full Windows environment is the most reliable approach.

By combining tools such as Docker and QEMU/KVM, advanced workflows and automated environments can also be built.

7. Using WSL (Windows Subsystem for Linux)

Up to this point, we have focused on running Windows applications on Ubuntu.
However, there is also an opposite approach: running Ubuntu inside Windows.
This is made possible by WSL (Windows Subsystem for Linux).

With WSL, Ubuntu can run almost natively on Windows, and Windows .exe files can be executed directly from the Ubuntu environment.
This section explains how WSL works, how to set it up, and how to run .exe files through it.

7.1 What Is WSL? — “Ubuntu Inside Windows”

WSL (Windows Subsystem for Linux) is a technology developed by Microsoft that allows Linux environments to run directly on Windows.
Unlike traditional virtual machines, WSL integrates closely with the Windows kernel, providing lightweight and high-performance Linux execution.

WSL 2, which is now the standard, uses a real Linux kernel and offers significantly improved compatibility and performance.

7.2 Installing Ubuntu on WSL 2

① Enable WSL

Open PowerShell as an administrator and run the following command:

wsl --install

This command installs WSL 2 and Ubuntu automatically.
If WSL 1 is already installed, upgrade it with:

wsl --set-default-version 2

② Launch Ubuntu

After installation, “Ubuntu” will appear in the Start menu.
On first launch, you will be prompted to create a username and password.

7.3 Running Windows .exe Files from Ubuntu (WSL)

A key advantage of WSL is the ability to launch Windows applications directly from the Ubuntu terminal.

notepad.exe

This command launches Windows Notepad.
Any Windows executable can be invoked by appending .exe.

explorer.exe .
calc.exe
cmd.exe

This allows Ubuntu commands and Windows applications to be combined seamlessly.

Seamless File Sharing

From Ubuntu running under WSL, Windows filesystems are accessible under paths such as:

/mnt/c/

Example:

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

This makes it easy to download files in Ubuntu and open them using Windows applications.

7.4 Running Ubuntu Commands from Windows

The integration also works in the opposite direction.
From PowerShell or the Command Prompt, you can run Ubuntu commands directly:

wsl ls -la
wsl python3 script.py

This makes WSL particularly useful for integrated development and testing workflows.

7.5 Limitations of WSL

7.6 Practical Development Use Cases

Example 1: VS Code + Ubuntu

With the “Remote – WSL” extension, Visual Studio Code can edit and run files directly inside Ubuntu.

Example 2: Docker on WSL 2

Docker Desktop integrates natively with WSL 2, enabling Linux containers to run efficiently on Windows.

Example 3: Combining Linux Tools and Windows Applications

Linux utilities such as ffmpeg, grep, and awk can be combined with Windows applications for flexible workflows.

7.7 Summary of WSL Pros and Cons

7.8 Summary

WSL is the easiest way for Windows users to start using Ubuntu.
Its ability to run Windows .exe files directly from Ubuntu makes it ideal for hybrid Windows–Linux environments.

However, WSL is fundamentally different from running Windows applications on a standalone Ubuntu system.
Choose this approach based on whether your primary environment is Windows or Ubuntu.

8. Real-World Examples: Results of Running .exe Files on Ubuntu

This section summarizes the results of testing real Windows applications on Ubuntu using different methods.
Both successful and unsuccessful cases are presented to provide realistic expectations.

8.1 Test Environment

• OS: Ubuntu 22.04 LTS (64-bit)
• CPU: Intel Core i7
• Memory: 16 GB
• Graphics: NVIDIA GTX series (proprietary driver installed)
• Wine: WineHQ Stable 9.x
• Virtualization: VirtualBox 7.x (Windows 10 Pro 64-bit guest)
• WSL: Windows 11 Pro + Ubuntu 22.04 (WSL 2)

8.2 Successful Cases

① Notepad++

• Method: Wine
• Result: Fully functional with no character issues
• Comment: Lightweight applications work extremely well with Wine

wine notepad++.exe

Startup time: approximately 3 seconds
Settings and plugins function normally.

② 7-Zip

• Method: Wine and Virtual Machine
• Result: Stable operation in both environments

Practical Rating: ★★★★★

③ Paint.NET

• Method: Wine + winetricks (dotnet40)
• Result: Usable for light image editing

Practical Rating: ★★★★☆

8.3 Conditionally Successful Cases

① Excel Viewer

• Method: Wine + winetricks (vcrun2015, msxml6)
• Result: Files open correctly, printing unstable

Practical Rating: ★★★☆☆

② RPG Maker Games

• Method: Wine
• Result: Title screen loads, some audio and image issues

Practical Rating: ★★☆☆☆

③ LINE (Windows Version)

• Method: Wine + winetricks
• Result: Login screen loads, notifications unsupported

Practical Rating: ★★★☆☆

9. Final Conclusion — Choosing the Right Method

Running .exe files on Ubuntu is entirely possible, but the optimal approach depends on your priorities.

• For lightweight tools and quick tests → Wine
• For maximum compatibility and business use → Virtual Machines
• For Windows-centered development workflows → WSL

Understanding the technical background and trade-offs allows you to choose the most efficient and reliable solution for your environment.