Azure CLI DLL Load Failed While Importing win32file – Windows Fix

If Azure CLI suddenly fails on Windows with the message “DLL load failed while importing win32file”, you’re dealing with a known Azure CLI regression, not a local system issue. This error causes every az command to crash instantly, making Azure management impossible on affected machines.

The problem is tied to a broken Windows build of Azure CLI (v2.77.0) that ships with a faulty embedded Python runtime, triggering a win32file ImportError during startup. In this guide, you’ll find a clear explanation of why the error happens, how to fix it safely in minutes, and how to avoid similar Azure CLI breakages in future updates.

Quick Fix (Recommended)

If you just want Azure CLI working again, follow these steps:

1. Uninstall Azure CLI v2.77.0
2. Install Azure CLI 2.76.0 (last stable Windows build)
3. Restart PowerShell or Command Prompt
4. Run:

az --version

Your commands should now run normally without the DLL error.

What Causes the “DLL Load Failed While Importing win32file” Error?

Starting with Azure CLI v2.77.0, Microsoft changed how Python is bundled on Windows.

Azure CLI now ships with an embedded Python runtime, instead of relying on a system Python installation. In this specific release, one of the critical Windows libraries — pywin32 — fails to load correctly.

During startup, Azure CLI initializes telemetry through an internal dependency (portalocker). That process attempts to import the win32file module. Because the bundled DLL is broken, the import fails immediately, and every az command crashes before execution.

Common Error Messages You May See

Depending on your setup, the failure may appear slightly differently. All of these point to the same root issue:

• ImportError: DLL load failed while importing win32file
• pywin32 ImportError Azure CLI
• portalocker win32file error
• az command crashes on startup Windows
• Azure CLI fails immediately with Python traceback

Fix: Uninstall the Broken Azure CLI Version

Step 1: Remove Azure CLI Completely

1. Open Settings → Apps → Installed Apps
2. Uninstall Microsoft Azure CLI
3. Manually delete any leftover folders (important):

C:\Program Files\Microsoft SDKs\Azure\CLI2

or

C:\Program Files (x86)\Microsoft SDKs\Azure\CLI2

This ensures the corrupted Python runtime is fully removed.

Install Azure CLI 2.76.0 (Last Stable Windows Build)

Option A: Download the Official MSI (Recommended)

Download the stable installer directly:

azure-cli-2.76.0-x64.msi

Run the installer and complete setup normally.

Option B: Install Using Winget (If Available)

winget uninstall --id Microsoft.AzureCLI -e
winget install --id Microsoft.AzureCLI -e --version 2.76.0

Verify the Fix

After installation, open a new PowerShell window and run:

az --version

You should see version 2.76.0, and Azure CLI commands should execute without any Python or DLL errors.

Optional Sanity Checks (If You Still See Issues)

If problems persist, check the following:

• Ensure PYTHONHOME and PYTHONPATH are not set in system environment variables
• Restart your terminal after reinstalling
• Temporarily whitelist the Azure CLI folder in antivirus software (some tools quarantine pywin32 DLLs)
• Avoid mixing Microsoft Store and MSI installations

Why This Error Happens Only on Windows

Linux and macOS builds of Azure CLI do not rely on pywin32, which is specific to Windows file APIs. The failure occurs because the Windows CLI package includes a faulty compiled DLL that cannot be loaded by Python at runtime.

That’s why:

• Cloud-based environments work fine
• Azure Cloud Shell is unaffected
• The issue does not appear on non-Windows systems

Temporary Workaround: Use Azure Cloud Shell

If you need Azure CLI immediately and can’t reinstall locally, use Azure Cloud Shell.

It runs Azure CLI in a fully isolated environment inside your browser and is not affected by this Windows bug. This is a safe short-term workaround for production tasks.

When Will Microsoft Fix This?

Microsoft is expected to resolve the issue in a future release (such as 2.77.x or 2.78).

Before upgrading again:

• Check Azure CLI release notes
• Look for explicit mentions of Windows DLL or pywin32 fixes
• Avoid running az upgrade blindly on production systems

How to Prevent Similar Azure CLI Breakages

To avoid downtime from future regressions:

• Pin Azure CLI versions in CI/CD pipelines
• Test new versions on a non-production machine first
• Keep a local copy of a known-stable MSI installer
• Avoid auto-updating critical CLI tools

These precautions ensure your automation and scripts are not disrupted by unexpected upstream changes.

FAQs

What does “Azure CLI DLL load failed while importing win32file” mean?

It means Azure CLI cannot load a required Windows DLL from its embedded Python runtime, causing every az command to crash before execution.

Why does Azure CLI fail with the win32file error on Windows?

This happens due to a broken pywin32 dependency bundled in Azure CLI v2.77.0, which prevents the win32file module from loading correctly during startup.

Which Azure CLI version causes the win32file DLL error?

The issue is confirmed in Azure CLI v2.77.0 on Windows, while earlier versions like 2.76.0 work normally.

Does this Azure CLI error affect Windows 10 and Windows 11?

Yes, the error affects both Windows 10 and Windows 11 because it is caused by the Azure CLI Windows build itself.

Is this error related to my installed Python version?

No, Azure CLI uses its own embedded Python runtime, so your system Python installation does not cause this error.

How do I fix Azure CLI DLL load failed win32file error?

Uninstall Azure CLI v2.77.0, remove leftover folders, reinstall Azure CLI 2.76.0, then restart PowerShell and verify with az --version.

Will upgrading Azure CLI fix the win32file DLL error?

Not until Microsoft releases a Windows build that explicitly fixes the DLL issue, so upgrading without confirmation is not recommended.

Can I use Azure Cloud Shell instead of fixing this locally?

Yes, Azure Cloud Shell runs Azure CLI in a browser-based environment and is not affected by this Windows DLL issue.

Should I remove PYTHONPATH or PYTHONHOME variables?

Normally no, but removing them can help rule out rare conflicts if they were manually configured.

How can I prevent Azure CLI from breaking after future updates?

Avoid automatic upgrades, pin stable versions in scripts, test updates on a secondary system, and keep a rollback installer ready.

If your Azure CLI suddenly stopped working with a win32file DLL load error, the cause is known, reproducible, and fixable. Rolling back to Azure CLI 2.76.0 restores full functionality and stability on Windows.