Environment

• Windows 10, x86_64
• sentry-cli v2.25.3

Steps to Reproduce

1. Open Visual Studio 2019 Developer Command Prompt
2. Build a C++ project using cmake with CMAKE_BUILD_TYPE set to RelWithDebInfo
3. Run: sentry-cli upload-dif -o %SENTRY_ORGANIZATION% -p %SENTRY_PROJECT% --log-level=debug .

Expected Result

All debug information files should be uploaded to Sentry.

Actual Result

The sentry-cli call fails with exit code 1. The following message is printed:

error: Invalid checksum

This runs on a Windows VM. Please note that I run similar jobs on macOS and Linux VMs on the same computing cluster, which also call sentry-cli upload-dif with similar inputs at some point. Neither of these ever fail because of Sentry, only the Windows job does.

Logs

Here are (sanitized) logs from a typical run: sentry_fail.log