Fix Azure CLI “DLL Load Failed While Importing win32file” Error on Windows

If every az command fails in PowerShell with a Python traceback ending in

ImportError: DLL load failed while importing win32file

This error appeared for many Windows users after updating Azure CLI to v2.77.0. The problem lies inside the bundled Python runtime, not your system’s Python.

Why Azure CLI Commands Fail

Starting with v2.77.0, Microsoft’s Azure CLI for Windows ships with an embedded Python runtime. In this release, one of the critical libraries (pywin32, which provides access to Windows file APIs) failed to load correctly.

When Azure CLI tries to initialize telemetry via portalocker, the win32file module triggers an ImportError. Because the failure occurs during startup, every az command—no matter which one—crashes before execution.

So, it’s not your environment or your PowerShell—it’s the CLI build itself.

Fix: Azure CLI DLL load failed win32file

1. Uninstall the Broken Version

Remove Azure CLI completely:

1. Open Settings → Apps → Installed Apps.
2. Uninstall Microsoft Azure CLI.
3. Manually delete any leftover folder:

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

or

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

2. Reinstall the Last Stable Version (2.76.0)

There are two safe ways to do this:

Option A – Download MSI directly

https://azcliprod.blob.core.windows.net/msi/azure-cli-2.76.0-x64.msi

Run the installer and follow the prompts.

Option B – Use Winget (if the version is still available)

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

3. Verify Installation

After reinstalling:

az --version

You should now see version 2.76.0 and no Python error.

4. Optional Sanity Checks

• Ensure PYTHONHOME and PYTHONPATH are not set in environment variables.
• Whitelist the Azure CLI directory in your antivirus (some tools quarantine pywin32 DLLs).
• Restart PowerShell to clear any cached sessions.

5. When Microsoft Releases the Fix

Keep an eye on Azure CLI release notes or GitHub issues. Once a newer version (2.77.x or 2.78) mentions “Windows DLL fix,” update safely:

az upgrade

or reinstall using the same MSI URL pattern (replace the version number).

Temporary Workaround: Use Azure Cloud Shell

If you need az immediately and can’t reinstall, open Azure Cloud Shell.

It runs a fully functional Azure CLI inside your browser, isolated from your local environment, and is unaffected by this Windows bug.

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How to Prevent Similar CLI Issues

To avoid breakages in future updates:

• Pin versions in CI/CD pipelines instead of running az upgrade blindly.
• Test new builds in a sandbox before rolling them into production scripts.
• Keep a local backup of a stable MSI (like 2.76.0) for rollback.

This approach ensures your automation isn’t at the mercy of an unexpected regression.