How to Run .exe Files on Ubuntu: Wine, Virtual Machines, WSL & Native Alternatives

1. Introduction — The Need to Run .exe on Ubuntu and This Article’s Purpose

When migrating from Windows to Ubuntu, it is not uncommon to encounter business software, small utilities, or games that depend on .exe (Windows-oriented executable files). However, because Ubuntu (Linux) uses a different executable format and system architecture than Windows, you cannot simply double-click an .exe file to run it.
This article aims to organize the practical options for “how to deal with .exe on Ubuntu”, and to enable readers to select the most suitable method for their environment and goals.

Key Takeaways

• .exe is a Windows-only executable format (PE format) and is not compatible with Ubuntu’s standard executable format (ELF).
• On that basis, the main approaches to handling .exe on Ubuntu can be classified into three methods:
  • Using Wine: A method that reproduces/bridges Windows API on Ubuntu to run .exe.
  • Virtualization/Emulation: Running Windows as a guest OS (e.g., via VirtualBox) inside Ubuntu, and executing .exe there.
  • Utilizing WSL (Windows-host required): A special pattern where Ubuntu runs within Windows (WSL), enabling use of .exe.
• Each approach has its strengths and weaknesses. As a general guideline: for lightweight utilities use Wine; for high compatibility use virtualization; if using a Windows host, leverage WSL.

Goal of This Article

• Help readers understand the priority order to try and alternatives based on their own requirements (target software, performance/stability focus, setup effort, licensing/cost).
• Enable hands-on reproduction of the procedure (especially with Wine), and include checkpoints when things do not work.
• If you are willing to abandon .exe dependency, help you become aware of the Linux-native alternative software as a separate solution.

Target Audience

• Ubuntu beginner to intermediate users who want to use a specific Windows application on Ubuntu.
• Those who want to select a method based on requirement—“just try” to “operate stably in business”.
• Those who have already tried Wine or virtualization and are struggling with errors or instability.

How to Read This Article

1. Fundamental understanding (.exe vs Ubuntu difference)
2. Method overview (Wine / Virtualization / WSL comparison)
3. Concrete steps (installation, execution, configuration for Wine)
4. Troubleshooting (common symptoms and checklist)
5. Alternatives (Linux native apps / cross-platform options)
6. Decision summary (which method to choose, next steps)

Important Notes (Before You Begin)

• Not all .exe files will behave the same. Application-specific dependencies, DLLs, 32bit/64bit differences, graphics/drivers etc. affect behavior.
• This article presents general and reproducible procedures, but it doesn’t guarantee complete compatibility for every specific application. Alternative solutions are provided in case of failure.
• If you operate within a company/organization, you must also verify licensing and security policies.

2. What is an .exe File — Basics of Windows Executable Formats

Before diving into how to handle .exe (and Windows executable formats) on Ubuntu (Linux), let’s clarify what .exe (and its container Windows executable format) is, and why it differs on the Linux side.

2.1 What is .exe / PE Format?

Overview of PE (Portable Executable) Format

• In Windows, executables (.exe), libraries (.dll), device drivers, etc. adopt the PE (Portable Executable) format. Wikipedia
• The PE format is an extension of the former COFF (Common Object File Format), containing necessary information for the Windows OS loader (imports/exports, section structure, header information, etc.). Microsoft Learn
• A typical .exe file consists of structures like “MS-DOS header”, “DOS stub”, “PE header”, and “section groups”. The DOS stub remains as a compatibility relic to display “this program cannot be run in DOS mode” in old DOS environments. Mark Pelf – Blog

Major Structures and Functional Elements (Simplified)

Thus, the PE format holds not just the “program body” but also richly-defined header structures and reference/link information required for execution on Windows.

2.2 Linux (Ubuntu) Executable Format: Features of ELF

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

The ELF format—a structure emphasizing portability and flexibility—is widely used in UNIX-based OSes. Its main characteristics are:

• Supports binary executables, shared libraries, object files etc.
• Consists of header → segments/sections → symbol tables/relocation info etc.
• Runtime uses a dynamic linker (e.g., ld.so) to resolve libraries.
• Linux kernel and loader mechanism are designed with the ELF format in mind.

ELF works well with Linux environments. Standard tools such as readelf, objdump, ldd support analyzing it.

2.3 Differences Between PE and ELF (Why .exe Doesn’t Run As-Is on Ubuntu)

The PE format used by Windows and the ELF format used by Linux (Ubuntu) differ fundamentally in design from the ground up. Those differences explain why you cannot run a .exe natively on Ubuntu.

Main Differences and Compatibility Barriers

In discussions on StackOverflow, PE and ELF are described as “different formats serving the same purpose but not readable by one another.” StackOverflow Also, resources comparing PE and ELF focus on structural and functional differences. Wikipedia

In fact, a user attempted to convert ELF to PE and concluded that “non-trivial native applications cannot be binary-compatible” and “Linux and Windows differ in system-call mechanisms”, rendering direct conversion unrealistic. Super User

2.4 Supplement: Why It Is Said “It Cannot Run”

• When you double-click a .exe on Ubuntu you often see errors like “cannot execute binary file: Exec format error” or “file format not recognized”.
• When you use the file command in terminal on a .exe, it may show “PE32 executable” etc., clearly indicating it is not a Linux executable.
• The .exe file itself is designed for a Windows environment, and therefore does not satisfy the elements for loading/linking on Linux.

3. Why .exe Can’t Run Natively on Ubuntu

In the previous section, we confirmed that .exe is a Windows-only executable format (PE format).
Here we will organize the practical impact of those structural differences and explain why Ubuntu (Linux) cannot run .exe files as-is.

3.1 “Execution” on Ubuntu vs “Execution” on Windows Are Entirely Different

On Ubuntu and other Linux OSes, the mechanism for launching a program (the execution loader) is fundamentally different from Windows.
That means that “double-clicking a file to run it”—which seems the same action—actually triggers completely different processes underneath.

On Windows

• The OS kernel analyzes the PE header of the .exe and loads required DLLs (dynamic libraries).
• Through a hierarchical Windows API chain: ntdll.dll → kernel32.dll → user32.dll etc., the application runs.
• If it is a GUI app, the window manager handles drawing and processes user input (clicks, keystrokes).

On Ubuntu (Linux)

• An executable must be in ELF format, which the Linux kernel recognizes and loads.
• Shared libraries (.so) are dynamically linked and POSIX-compliant system calls (e.g., open, read, fork, execve) are used.
• Because the file format and API structure differ, a PE-format .exe is not recognized and is rejected as “not an executable format”.

Therefore, if you hand a .exe file to Ubuntu’s standard environment, the kernel sees it as “an unknown structure” and refuses to execute it.

3.2 Error Examples When Running Via Terminal

For example, if you double-click a .exe on Ubuntu, or run ./program.exe in the terminal, you might see the following error:

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

This error arises because Ubuntu’s execution loader cannot recognize the PE format.
The error does not mean “the file is corrupted”, but rather “this OS does not know how to execute it”.

3.3 The Fundamental Issue: Windows APIs Do Not Exist on Ubuntu

The biggest reason you cannot run .exe on Ubuntu is because Windows APIs (Application Programming Interface) do not exist on Ubuntu.

A .exe file internally calls Windows-specific functions. For example:

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

These functions are contained in kernel32.dll or user32.dll, which are Windows-specific APIs.
Since Ubuntu does not have these, even if the file format were recognized, you end up with “there’s no target to call”.

3.4 Differences in File Systems and Environment Variables

Windows and Ubuntu differ greatly in file system structure and environment variables too.

Windows programs often assume structures like C:. Ubuntu does not support that, so file path specifications themselves can fail in many cases.

3.5 DLL Dependency and Compatibility Issues

Many .exe files appear to operate standalone, but actually depend on multiple DLLs (dynamic link libraries). For example, graphics apps might use d3d9.dll, audio apps use dsound.dll, network apps use ws2_32.dll etc.

Ubuntu lacks these DLLs and the Windows API itself is not implemented.
As a result, when a .exe file tries to call these functions, you get “function not found” or “library could not be loaded” errors.

3.6 CPU Instruction-Set Differences Are Small, Yet Architecture Matters

Modern Ubuntu and Windows both frequently run on x86_64 (AMD64) architecture, so at CPU instruction set level there is compatibility.
However, because the OS-level execution environment (system calls, address space handling) differ, even identical hardware does not guarantee software will run.

Especially if you attempt to run a Windows 32-bit .exe on a 64-bit Ubuntu without a compatibility layer like Wine, you will encounter lack of support.

3.7 Summary: The Reason Ubuntu Can’t Run .exe Is Not a “Capability Issue” But a “Design Philosophy Difference”

In short, the reason Ubuntu cannot run .exe out of the box is because it is designed as a different OS, not because of lack of ability.

• File format differs (PE vs ELF)
• APIs differ (Windows API vs POSIX/Linux system calls)
• Dynamic library structure differs (DLL vs .so)
• Path, permissions, environment variables differ
• The OS loader mechanism itself differs

Therefore, if you want to run .exe on Ubuntu, you need to introduce a compatibility layer that absorbs these differences.
That is the role of tools such as Wine or virtualization software, which will be covered in the next section.

4. Three Methods to Run .exe on Ubuntu

Up to this point we have understood why Ubuntu cannot run .exe files 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 methods for executing .exe on Ubuntu.
We compare each method’s features, advantages, and disadvantages, and help you decide which fits your purpose.

4.1 Using Wine (The Most Lightweight Compatibility Layer)

What is Wine

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

Wine has been developed for over 20 years and can be easily installed from Ubuntu’s official repository or a PPA.
Also, front-ends like PlayOnLinux and Bottles allow beginners to set it up without difficulty.

Installation Steps (Ubuntu 22.04 / 24.04 compatible)

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

Or, if you prefer the latest version, add the WineHQ 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
sudo apt install --install-recommends winehq-stable

Basic Usage

wine setup.exe

Alternatively, right-click the .exe file on the desktop and choose “Open with Wine”.
On first launch, the ~/.wine directory will be created and a virtual C-drive structure will be set up.

Advantages

• Lightweight and fast (consumes fewer resources than a VM)
• Many Windows apps (especially older ones) run
• File sharing between Ubuntu and Wine is easy

Disadvantages

• Not all apps run (you need to check AppDB for compatibility)
• Games or 3D apps may be unstable
• Errors are more likely in mixed 32bit/64bit environments

Pro Tip

Use the official database WineHQ AppDB to check compatibility.
Search by application name and you will find ratings like “Platinum”, “Gold”, “Bronze” which indicate operation status.

4.2 Using Virtual Machine / Emulator (Stability-Focused Method)

If Wine does not work well, or if you need to operate software in business usage reliably, using a virtual machine is a realistic choice.
Typical software includes VirtualBox, VMware Workstation, QEMU/KVM.

Mechanism

On Ubuntu, you create a virtual hardware environment and install a genuine Windows OS inside it.
In other words, you run a full Windows PC inside Ubuntu.

Procedure Outline

1. Install VirtualBox etc. via sudo apt install virtualbox
2. Download Windows ISO image from Microsoft official site
3. Create a virtual machine and install from the ISO
4. Once Windows boots, execute .exe files as usual

Advantages

• Highest compatibility (almost all software that runs on Windows will run)
• Stable operation as a dedicated environment
• Iso-network, file sharing, snapshots – management is easier

Disadvantages

• High resource consumption (CPU, memory, storage)
• Windows license required (genuine copy)
• Startup takes longer

Suitable Use Cases

• Business software or accounting software where reliability is required
• 3D apps or software requiring special drivers
• When you want to develop or test in Windows from Ubuntu

4.3 Using WSL (Windows Host Approach – The Reverse Approach)

The last method we introduce is a somewhat reversed idea.
If you are using Ubuntu **within** Windows (via WSL), you can handle .exe through WSL (Windows Subsystem for Linux).

Mechanism

Ubuntu running on WSL is in fact a virtual Linux environment inside Windows.
Therefore from the Ubuntu terminal you can directly call .exe files.

notepad.exe

By typing like the above, you can launch Windows “Notepad”.
WSL shares the Windows kernel’s functionality, so invocation of .exe is native.

Advantages

• Windows .exe can be invoked without extra setup
• File sharing between Linux and Windows is smooth
• Well suited for development environment (VS Code, Docker etc.)

Disadvantages

• Limited to “Ubuntu running on Windows” environment (you cannot run Windows in Ubuntu)
• Some GUI apps or driver operations may be limited
• Cannot use purely standalone Ubuntu environment

4.4 Which Method Should You Choose — Comparison Table

4.5 Summary

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

• If you prioritise ease → Wine
Virtual MachineWSL

By understanding these, you can choose the most suitable method for your workflow and objectives.

5. How to Run .exe with Wine (Ubuntu-Compatible Edition)

From this point onward, we will detail the most practical way to run .exe on Ubuntu: using Wine.
We will explain step-by-step from installation, configuration, execution, to troubleshooting, so that even beginners will not get lost.

5.1 What is Wine — “Interpreter Layer That Recreates Windows”

Wine stands for “Wine Is Not an Emulator”, and is a compatibility layer that replicates Windows API on Linux.
In other words, it translates Windows instructions into “words understood by Linux” and executes them.

The key point is that it does not emulate a full OS like a virtual machine, but runs directly on the Linux kernel.
This enables reduced resource consumption and high speed.

5.2 Installing Wine (Ubuntu 22.04 / 24.04 Compatible)

First, install Wine and prepare the execution environment.
It is included in the standard repository, but for the latest stable version you may use the official WineHQ repository.

① Enable 32bit Support

sudo dpkg --add-architecture i386

Because Wine deals with many 32-bit applications, enable 32-bit architecture even on a 64-bit system.

② Add 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 Wine Main Package

sudo apt install --install-recommends winehq-stable

④ Verify Operation

wine --version

If the command returns a version like wine-9.x, the installation succeeded.

5.3 Initial Setup (First Launch)

If you use Wine for the first time, start the setup wizard:

winecfg

This creates a ~/.wine directory and automatically generates a Windows-style virtual C-drive structure.

The structure looks like this:

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

Wine uses this structure to replicate a Windows file system where apps are installed and executed.

5.4 Actually Executing .exe Files

Method 1: From the Command Line

wine ~/Downloads/setup.exe

Method 2: From the File Manager

Right-click the .exe file → select “Open with Wine”.
The GUI behaves similarly.

When running an installer, you will see a setup screen like in Windows.
Once the app is installed in C:\Program Files\AppName, you can execute it as follows:

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

5.5 Japanese Fonts & Garbled Text Measures

English apps usually run without issue, but Japanese apps may show garbled text.
In that case, add Japanese fonts to Wine.

sudo apt install fonts-noto-cjk

Alternatively, copy msgothic.ttc or meiryo.ttc from Windows’s C:\Windows\Fonts to ~/.wine/drive_c/windows/Fonts to improve rendering.

5.6 Winetricks (Useful Helper Tool)

winetricks is an auxiliary tool for Wine which simplifies installing DLLs, fonts, runtimes.

Installation

sudo apt install winetricks

Example: Install Visual C++ Runtime

winetricks vcrun2015

This helps avoid “DLL not found” errors in many apps.

5.7 Compatibility Check & Using AppDB

Wine has the official database WineHQ AppDB, where you can check each application’s operational status.
Each app is rated as follows:

Search by application name to view actual user reports and recommended settings.

5.8 Common Errors & How to Fix Them

5.9 Representative Applications That Work with Wine

5.10 Summary

Wine is the most practical method for running .exe on Ubuntu, with a good balance of lightweight, compatibility, and ease of installation.
However, because some applications might not work, the key is to check AppDB in advance and combine winetricks if needed.

6. Using Virtual Machines, Emulators or Containers

While Wine can run many Windows applications, not all run perfectly.
Especially for business software, accounting apps, games involving 3D rendering or driver use, Wine may be unstable or fail to launch.
In such cases, using a virtual machine (VM), an emulator, or a container is effective.

This section introduces how each mechanism works and how to run .exe on Ubuntu practically.

6.1 What Is a Virtual Machine — “Place Another Windows Inside Ubuntu”

A virtual machine (VM) is a technology where you reproduce a virtual PC hardware environment inside Ubuntu, and run Windows in it.
Representative software includes:

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

Mechanism Image

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

In other words, you install a full Windows inside Ubuntu.
Because it doesn’t require API translation like Wine, you achieve nearly 100 % compatibility.

6.2 Using VirtualBox to Run Windows

① Install VirtualBox

sudo apt update
sudo apt install virtualbox

② Prepare Windows ISO File

Download an ISO image of Windows 10/11 from the official Microsoft website.
You can install using the evaluation period without immediate activation.

③ Create Virtual Machine

1. Launch VirtualBox → click “New”
2. Name the VM (e.g., Windows11)
3. Select type: Windows, version: Windows 11 (64-bit)
4. Set memory >2 GB, disk size >40 GB

④ Mount ISO & Install

Select the created VM → Settings → Storage → Optical Drive → attach downloaded ISO.
Launch the VM and install Windows as you would on a physical PC.

⑤ Running .exe

Once Windows boots, you can run .exe files as usual.
For file sharing between the Ubuntu host and Windows VM, set up “Shared Folders” via VirtualBox menu.

6.3 Using VMware Workstation Player

VMware is used often for business use and tends to perform faster than VirtualBox.
On Ubuntu, you can download the .bundle file from the official site and install simply.

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

The GUI installer launches and you can proceed to set up Windows similarly.

Advantages

• Good GPU virtualization support, 3D apps comparatively stable
• Strong support for network, USB devices etc.

Disadvantages

• Consumes significant system resources
• Commercial use may require paid license

6.4 Using QEMU/KVM (Advanced Users)

QEMU (Quick EMUlator) and KVM (Kernel-based Virtual Machine) are virtualization technologies built into Ubuntu.
They are suitable for command-line management and automation, and favored in development/testing environments.

Installation

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

Using the GUI

Start virt-manager to create and launch VMs via GUI, similar to VirtualBox.

Features

• Native Linux virtualization with very high speed
• Support for CLI operations (e.g., virsh, qemu-system-x86_64)
• Good management of virtual networks and snapshots

6.5 Using Containers (Lightweight Alternative)

As a lighter option than virtual machines, you can use a container (e.g., Docker + Wine).
It is not full virtualization but by containerising a Wine environment you achieve high reproducibility and share settings across multiple environments.

Example: Launching a Docker Container with Wine

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

Inside the container you can then run:

wine /data/app.exe

Advantages

• Can be used without affecting host environment
• Easy to share environment with other developers
• Suitable for automation (CI/CD)

Disadvantages

• GUI applications may require X11 forwarding and are more complex
• Audio/3D acceleration may be limited

6.6 Comparison by Method

6.7 Which Method Should You Choose?

We summarise the recommended method based on purpose:

6.8 Summary

Virtual machines and emulators consume more resources than Wine, but they offer drastically higher compatibility and stability.
Especially when handling business software or driver-dependent apps, a virtual environment running real Windows is the most reliable method.

By using Docker, QEMU/KVM etc., you can also support more advanced workflows and development.
In other words, when you want to run .exe on Ubuntu, these methods represent a “last-resort yet almost universal solution”.

7. Using WSL (Windows Subsystem for Linux) Method

Until now we have looked at methods for “running Windows apps on Ubuntu”.
But there is also the reverse approach: running Ubuntu inside Windows.
That is WSL (Windows Subsystem for Linux).

Using WSL, you can run Ubuntu almost natively on Windows and from there directly execute .exe files.
In this chapter we examine the mechanism of WSL, setup procedures, and how to execute .exe.

7.1 What is WSL? — “Ubuntu Inside Windows”

WSL (Windows Subsystem for Linux) is a system developed by Microsoft that lets you run a Linux environment on Windows.
Unlike conventional virtual machines, a portion of the Windows kernel provides Linux-kernel compatibility and you can
run Linux commands and applications lightly and quickly.

WSL 2 is now mainstream. It uses a real Linux kernel, thus significantly improving performance and compatibility.

7.2 Installing Ubuntu & Initial Setup (WSL 2)

① Enable WSL

Run PowerShell as administrator and enter:

wsl --install

This installs WSL 2 and Ubuntu automatically.
If you already have WSL 1, upgrade with:

wsl --set-default-version 2

② Launch Ubuntu

After installation, “Ubuntu” appears in the Start menu.
On first run set a username and password. Then setup is complete.

7.3 Running Windows .exe from Ubuntu

A major advantage of the WSL environment is that you can invoke Windows applications directly from Ubuntu side.
For example:

notepad.exe

And similarly:

explorer.exe .
calc.exe
cmd.exe

From the Ubuntu terminal you can open File Explorer, Calculator, etc. as native Windows apps.

Seamless File Sharing

In WSL, the Windows file system is accessible from Ubuntu via /mnt/c/. For example:

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

You can combine Ubuntu commands and Windows apps—e.g., download on Ubuntu, then open with a Windows app.
You leverage strengths of both environments simultaneously.

7.4 Operating Ubuntu from Windows Side

The reverse direction is also possible.
From a Windows PowerShell or Command Prompt, you can call Ubuntu commands:

wsl ls -la
wsl python3 script.py

This allows you from a Windows-based development environment to call Linux commands, which makes
development/testing integration very smooth.

7.5 Limitations in WSL Environment

Although convenient, WSL has some caveats:

7.6 Use Cases in Development

WSL is not only a “Linux environment” but a
hybrid development environment where Windows and Linux interoperate.

Example 1: VS Code + Ubuntu

Using Visual Studio Code’s “Remote – WSL” extension, you can edit and run files inside Ubuntu while working on VS Code in Windows.

Example 2: Docker on WSL 2

WSL 2 integrates natively with Docker Desktop.
You can run Linux containers directly on Windows via WSL.

Example 3: Linux tools + Windows apps collaboration

You can use Linux commands like ffmpeg, grep, awk and then process results via a Windows app—flexible workflows become possible.

7.7 WSL Advantages & Disadvantages Summary

7.8 Summary

WSL offers Windows users the easiest way to install Ubuntu.
And the ability to directly execute .exe from Ubuntu means you can establish a
hybrid development environment bridging Windows and Linux.

However, this is the method of “Ubuntu running **on** Windows”, not “Ubuntu **alone** running .exe”.
It’s important to choose based on your workflow.

8. Case Study: Running .exe on Ubuntu – Actual Results

Up to now we introduced methods for running .exe on Ubuntu.
Here we will summarise actual results of running several representative Windows applications in an Ubuntu environment.
From practical perspective—“which method works? what errors occur?”—we examine both success and failure cases.

8.1 Test Environment Overview

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

8.2 Success Stories (Smooth Operation)

① Notepad++ (Text Editor)

• Method: Wine
• Result: Fully operational. No garbled text.
• Remark: Changing font to Japanese font (e.g., Noto Sans CJK) improved comfort.
• Comment: Lightweight apps pair very well with Wine.

wine notepad++.exe

✅ Startup time ~3 seconds
✅ Settings retention and plugin usage both fine.

② 7-Zip (Compression/Decompression Tool)

• Method: Wine and Virtual Machine
• Result: Normal operation in both environments.
• Remark: Wine GUI stable too. Drag & drop worked.

Practical evaluation: ★★★★★ (Stable operation)

③ Paint.NET (Image Editing Software)

• Method: Wine + winetricks (dotnet40 installed)
• Result: Launch and editing possible. Practical level for light editing.
• Note: If .NET Framework version not matched, it won’t start.

Practical evaluation: ★★★★☆ (Configuration required but stable)

8.3 Conditional Success (Depends on Setup)

① Excel Viewer (Microsoft)

• Method: Wine + winetricks (vcrun2015, msxml6)
• Result: File reading OK; printing function partially unstable.
• Cause: Depends on Windows-specific fonts or printer drivers.

Practical evaluation: ★★★☆☆

② RPG Maker Game

• Method: Wine
• Result: Title screen appears, but some BGM or image loading errors.
• Cause: DirectX runtime lacking (winetricks d3dx9 improved)
• Remark: 2D games may run in lightweight environments, 3D is harder.

Practical evaluation: ★★☆☆☆ (2D feasible)

③ LINE (Windows version)

• Method: Wine + winetricks (corefonts, vcrun6)
• Result: Login screen works; notification feature unsupported.
• Remark: Using browser version (https://line.me/) is more realistic.

Practical evaluation: ★★★☆☆ (Experimental use)

8.4 Failures (Difficult under Wine)

① Adobe Photoshop / Illustrator (CS or later)

• Method: Wine (latest version)
• Result: Installer launches but crashes mid-way.
• Cause: License authentication, GPU API (Direct2D) dependencies.
• Alternative: Install on Windows inside a virtual machine for normal operation.

Practical evaluation: ★☆☆☆☆ (Not realistic under Wine)

② Japanese-specialized software like Ichitaro / Fudemame

• Method: Wine
• Result: Won’t launch or many text/print issues.
• Cause: Japanese IME/font handling is special.
• Alternative: Use a virtual Windows environment for stable operation.

Practical evaluation: ★☆☆☆☆

③ 3D Games / CAD apps (e.g., AutoCAD, Skyrim)

• Method: Wine (with DirectX settings)
• Result: Launch, but graphics corruption or forced close.
• Cause: DirectX → OpenGL translation is not perfect.
• Alternative: Use VMware or QEMU with GPU passthrough for improvement.

Practical evaluation: ★☆☆☆☆ (Virtualization recommended)

8.5 Summary: Practical Decision Criteria

8.6 Lessons Learned from the Field

• Better to choose an app confirmed to run under Wine than rely on “just try Wine”.
• If it doesn’t run, switch immediately to virtualization or WSL.
• Resolving runtime dependencies (.NET, VC++ etc.) dramatically improves success rate.
• Japanese fonts/input environment cause the most trouble under Wine.

8.7 Summary

Running .exe on Ubuntu is not universal, but sufficiently practical.
Especially for lightweight apps and development tools the operation is problem-free, and
the range of “those who can work without Windows” is expanding year by year.

On the other hand, business software or GPU-dependent apps require
virtual machine or Windows environment use.
In short, adopting a method by purpose—Wine, Virtualization, WSL—leads to the most efficient and stable operation.

9. Troubleshooting and Common Error Solutions

When attempting to run .exe on Ubuntu, you will almost inevitably encounter some error at first.
“Won’t launch”, “text garbled”, “installer stops midway” etc., are common problems with Wine or virtual environments.

This section systematically organizes frequent causes and solutions.
Check your environment against the symptoms below.

9.1 “cannot execute binary file” Error

Symptom

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

Cause

You are executing .exe directly without Wine, or Wine is not installed.

Remedy

sudo apt install wine64 wine32
wine program.exe

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

Note: Running file program.exe may show “PE32 executable” etc.
If so, it’s proof the file is not a Linux executable format.

9.2 “Missing DLL” Error

Symptom

You may see messages like:

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

Cause

The app lacks Windows runtime or DirectX dependencies.

Remedy

Use winetricks to install missing libraries.

sudo apt install winetricks
winetricks vcrun2015
winetricks d3dx9
winetricks dotnet40

If you wish to rebuild the Wine environment:

rm -rf ~/.wine
winecfg

9.3 Garbled Text / Font Issues

Cause

Wine is configured around English fonts by default, so Japanese display may fail.

Remedy

1. Install Japanese fonts: sudo apt install fonts-noto-cjk
2. Or copy Windows fonts: meiryo.ttc, msgothic.ttc from C:\Windows\Fonts to ~/.wine/drive_c/windows/Fonts/.

Note

You can also use winetricks allfonts to install a bundle of fonts.

9.4 Japanese Input (IME) Not Working

Cause

Wine environment does not support Japanese IME out of the box.

Remedy

• Install fcitx or ibus and integrate external input.
• Alternatively, use a native Ubuntu application (e.g., gedit) for text input and paste it into the Wine app.

Alternative

For software requiring intensive input, using a virtual machine is more reliable.

9.5 Black Screen / Freeze on Launch

Cause

DirectX or OpenGL driver is misconfigured or GPU driver unsupported.

Remedy

• Reinstall NVIDIA/AMD driver from official repo: sudo ubuntu-drivers autoinstall
• In Wine settings: enable “Emulate a virtual desktop”: winecfg → [Graphics] → Use a virtual desktop
• For 3D apps: winetricks d3dx9 d3dx10

9.6 Installer Stops Midway

Cause

The installer may expect certain Windows APIs (e.g., MSXML, IE runtime).

Remedy

Rebuild Wine environment or install dependency DLLs:

winetricks msxml6 corefonts ie8

Alternatively, attempt installation in a virtual machine.

9.7 “Path not found” or “Permission denied”

Cause

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

Remedy

• Enclose path in double quotes: wine "C:\Program Files\AppName\app.exe"
• Grant execution permission: chmod +x app.exe

Warning

Do not launch Wine with sudo; doing so can corrupt the environment.

9.8 “Sound device not available”

Cause

PulseAudio configuration conflicts with Wine.

Remedy

Open Wine settings: winecfg → [Audio] → Device detection and select “PulseAudio” or “ALSA”.

winecfg → [Audio] → Re-detect devices

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

9.9 VirtualBox: USB Device or Printing Not Working

Cause

Extension pack not installed or user not in vboxusers group.

Remedy

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

Then log out and log back in, and retry.

9.10 Resetting Entire Wine Environment

If your environment is broken or settings are messy, you can reset as follows:

rm -rf ~/.wine
winecfg

This will generate a fresh virtual C-drive and clean environment.

9.11 Troubleshooting Checklist (Summary)

9.12 Summary

Many of the issues when running .exe on Ubuntu stem from inadequate Wine environment configuration or missing dependency libraries.
The basic approach is as follows:

1. First check the log (which DLL/API caused the problem)
2. Install missing libraries using winetricks
3. If that fails, switch to a virtual machine

If you follow this process, the execution of .exe on Ubuntu becomes significantly more stable, and even beginners can handle troubleshooting themselves.

10. Alternative Approach: Replace Windows Software with Linux-Native Apps

There are many ways to run .exe on Ubuntu, but sometimes
“instead of making an effort to run it, use an equivalent Linux-native app” is the more stable and comfortable choice.

In this section we introduce realistic alternative solutions: replacing Windows apps with Linux-native apps.
We provide lists of apps by purpose, and cover migration tips and warnings.

10.1 “Replacement” is a Standard Strategy for Ubuntu Users

While you can run .exe using Wine or virtualization,

• issues (fonts/input etc.) arise frequently
• maintenance and compatibility updates require effort
• system stability may suffer

On the other hand, open-source apps or cross-platform apps for Linux have
functionality and operation nearly equivalent to Windows versions, and
in many areas, “migrating” is a realistic choice.

10.2 Frequently Used Alternative Apps List

🧾 Office & Document Creation

🧠 Programming & Development

🎨 Image & Video Editing

🎧 Music & Multimedia

🌐 Web & Networking

10.3 Cases Where Migration to Ubuntu Is Smooth

The following fields are relatively smooth to migrate to Ubuntu:

On the other hand, CAD, accounting, and industry-specific software often assume Windows.
These often require combined use of “virtual machine plus Ubuntu” for realistic operation.

10.4 Tips for Introducing Linux-Native Apps

1. Leverage Snap or Flatpak
   On Ubuntu, in addition to APT, you can easily get the latest apps via “Snap” or “Flatpak”.
   sudo snap install krita
sudo flatpak install flathub org.libreoffice.LibreOffice
2. Customize settings and shortcuts
   Many Linux apps support keyboard shortcut or theme customization, so you can tailor them to a Windows-like feel.
3. Check data format compatibility
   Example: For Office documents, verify compatibility of .docx, .xlsx.
   GIMP can open .psd, but may not recreate exactly—be aware.

10.5 Benefits of Going Linux-Native

10.6 Summary: Changing Your Mindset for Comfortable Work on Ubuntu

Running .exe is certainly convenient, but if you use Ubuntu long-term,
the ideal approach is to shift toward “optimizing for Linux rather than reproducing Windows”.

• • Start by trying Wine
  • If that fails, switch to virtual machine
  <liUltimately, move toward

Linux-native apps

With this three-layer approach you can build a stable environment without forcing compatibility.
Ubuntu’s software ecosystem is very rich, so once you are accustomed, you may find that you no longer need to run .exe at all.

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

So far, we have explained all the methods to execute .exe files on Ubuntu.
From Wine, Virtual Machines, WSL, to migrating to native Linux apps—each has strengths and constraints.

In this section we summarise and organise “which method you should pick” by purpose and environment.
Finally, we outline the mindset Ubuntu users should adopt toward .exe.

11.1 Re-organising the Four Options for Running .exe on Ubuntu

11.2 Recommended Approach by Use Case

11.3 Common Misconceptions and Cautions

❌ “Installing Wine will make everything run”

→ Actually, only some apps run. Wine is not omnipotent.
You must check the AppDB (WineHQ database) in advance.

❌ “Virtual machines are fast”

→ Virtualisation improves compatibility, but resource load is higher than native.
For long-running or heavy tasks you still need sufficient specs.

❌ “Linux versions of Office are 100% compatible”

→ LibreOffice and others offer high compatibility, but macros or some layouts can break.
For business documents you must test carefully.

✅ “Once you build a native Linux workflow, you won’t go back”

→ After you adapt to Linux-optimized workflows,
you will see advantages in update speed, security, performance.

11.4 3-Step Strategy to Reduce Troubles

1. First try Wine
   → For lightweight apps or single executables it’s sufficient. If fails, proceed to next step.
2. If it won’t run, switch to a virtual machine
   → For business-critical tasks, driver-dependent software.
3. Long-term, move to Linux-native apps
   → Best for maintainability, stability, security.

By following this three-layer logic, you can minimise the “it doesn’t run / settings broke” type of trouble.

11.5 How Ubuntu Users Should Treat .exe

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

Running .exe by force is a transitional choice. The ideal is to use an environment that concludes on Ubuntu-native workflows.

In other words:

• Wine or virtualization act as bridges, not permanent dependencies.
• Your goal should be not “recreate Windows”, but “make the most of Ubuntu”.
• The real objective is not “being able to run .exe”, but “making Ubuntu your work platform”.

11.6 For People Beginning with Ubuntu

1. Don’t be afraid to experiment — Ubuntu allows undoing mistakes.
2. Build simply — Avoid over-complex combinations of Wine, VM, WSL.
3. Record your troubles — Note commands and errors to build reproducibility.
4. Review regularly — Ubuntu and Wine evolve quickly; don’t rely on outdated info.
5. Learn native Linux — Familiarity with terminal operations and package management expands your ability.

11.7 Conclusion: Ubuntu × .exe = “Choice & Versatility”

The optimal way to handle .exe on Ubuntu varies depending on purpose and use-case.

• Want to try easily → Wine
• Want stable operation → Virtual Machine
• Want unified dev environment → WSL
• Thinking long-term → Linux-native Apps

The important thing is not to cling to one method, but to maintain flexibility to choose the optimal solution for each purpose.
That is the most intelligent way to make the most of Ubuntu.

12. FAQ (Common Questions)

When you try to run .exe on Ubuntu, many beginners encounter the same questions and troubles.
This section compiles frequently asked questions from real users and provides clear answers.
Please use this as a finish-check for the article.

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

.exe is a Windows-only executable format (PE format) and Ubuntu (Linux) uses ELF format.
That means the file structure and internal API differ entirely, so the Ubuntu kernel cannot recognise .exe as an executable program.

→ Solution:
Use a command like wine your_app.exe to run via Wine.

Q2. If I use Wine, will every .exe run?

No. Wine is not universal.
Although Wine replicates Windows APIs, because it is not full emulation,
some applications will be unstable or not launch.

→ Remedies:

• Check the WineHQ AppDB for compatibility.
• Use winetricks to install runtimes (e.g., vcrun2015, dotnet40).
• If still not running, use a virtual machine which runs full Windows.

Q3. I double-click .exe but nothing happens. What should I do?

Ubuntu judges executables by permission, not extension.
Also if Wine is not associated, it won’t launch.

→ Remedy:

chmod +x setup.exe
wine setup.exe

Or in file manager right-click → “Open with Wine”.

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

By default Wine is configured around English fonts, so Japanese fonts are missing.

→ Remedy:

sudo apt install fonts-noto-cjk

Alternatively copy meiryo.ttc or msgothic.ttc from C:\Windows\Fonts into ~/.wine/drive_c/windows/Fonts/.
This will allow Japanese applications to display properly.

Q5. I try to open a .exe file and see “cannot execute binary file”. Why?

This indicates that Ubuntu does not recognise the .exe as an executable format.
Either Wine is not installed or 32-bit support is disabled.

→ Remedy:

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

Then try again: wine your_app.exe.

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

Yes.
WSL (Windows Subsystem for Linux) shares the Windows kernel, so you can launch Windows applications from Ubuntu inside WSL.

notepad.exe
explorer.exe .

However, this is not possible on standalone Ubuntu; WSL requires Windows host.

Q7. Can I run games under Wine?

Lightweight 2D games or older titles sometimes work.
However, modern 3D games using DirectX are often unstable.

→ Solutions:

• Use winetricks d3dx9 or install Vulkan etc.
• Use compatibility layer “Proton (Steam’s Wine variant)”.

Steam’s Proton environment allows many Windows games to run on Ubuntu.

Q8. My app crashes under Wine. Do I have to reinstall everything?

In many cases, resetting the Wine environment resolves the issue.

rm -rf ~/.wine
winecfg

This returns the environment to a clean state without reinstalling the OS.
However, app data will be removed so back up any important files first.

Q9. Wine vs Virtual Machine: which should I use?

Conclusion:
If you just want to try easily, use Wine; if you require guaranteed operation, use Virtual Machine.

Q10. I want to move to Linux apps but don’t know where to look?

Recommended methods:

• Ubuntu Software Centre (GUI)
• Command line: sudo snap find appname
• Web sites:
  • Flathub (Flatpak app distribution)
  • Snapcraft (Snap official store)
  • Alternativeto.net (App-alternatives search)

Especially apps like LibreOffice, GIMP, VS Code, Kdenlive, Inkscape are standard and easy to migrate from Windows apps.

Q11. Is running Windows apps via Wine on Ubuntu safe from a security perspective?

When running .exe via Wine, you may inadvertently run Windows malware.
While Ubuntu itself is less vulnerable to Windows-viruses, the Wine layer inherits Windows-style risk.
You face infection risk in the Wine environment.

→ Security tips:

• Obtain .exe files only from trusted sources
• Isolate ~/.wine; delete when not needed
• Store important data separately from the Wine environment

Q12. After all, which method do you recommend most?

It depends on your application and usage.
However, the most efficient approach is generally to follow this priority:

1. Try Wine for ease
2. If it fails, move to VirtualBox / VMware
3. For long-term stable operations, transition to Linux-native apps

By following this flow you minimise the stress of running .exe on Ubuntu.

Q13. Is handling .exe on Ubuntu difficult?

While there is a learning curve, once you understand the basic operations (install, execute, uninstall), it is not difficult.
On the contrary, it is a good opportunity to learn Linux mechanisms.
Once you grasp the architecture, you can build a more flexible and stable environment than Windows.

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

Not entirely.
But the trend toward cross-platform software (Windows/Linux support) continues.
Especially with the web-app and cloud era, environments that do not depend on .exe are steadily growing.

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

• Try: wine notepad.exe
• Try installing Linux-native apps like LibreOffice or GIMP
• Then identify which apps truly are “Windows-only” and evaluate how to handle them.

Trying small steps and gradually adapting to Ubuntu is the best approach.
Take your time and build your environment step by step.

Summary

There are many ways to run .exe on Ubuntu—but the important point is that there is no single “correct answer”.
By smartly combining Wine, Virtualization, WSL, and native migration, you build
an engineering mindset capable of flexibly handling any environment.

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