The issue here is env variables that point to the openssl installation are not set.

Setting all the variables specified in rust-openssl/rust-openssl#1542 (comment) should resolve this.

@youknowone you added the win32_xstat impl in #5247 - do you know why the tests fixed by that might be failing now with a windows update? It's not like they would've removed the api-ms-win-core-file-l2-1-4 API set.

I am sorry. I code like a monkey with wniapi. I really don't know well about their details.

I mentioned this link in #5583, but openssl prebuilts are also available from the cpython project here https://github.com/python/cpython-bin-deps/

Walkthrough

These changes update Windows build and CI configuration by pinning the Windows runner to windows-2025, replacing the vcpkg-based OpenSSL setup with direct path environment variables, removing OpenSSL bootstrap steps from CI workflows, and updating a Windows API library import to include the .dll extension.

Changes

Estimated code review effort

🎯 2 (Simple) | ⏱️ ~15 minutes

Possibly related PRs

• RustPython/RustPython#6148: Updates Windows runner pinning from windows-latest to windows-2025 in the same CI workflow matrices.

Poem

🐰 Hoppy improvements, oh what a sight!
Windows runners pinned just right,
OpenSSL paths now set with care,
vcpkg gone—cleaner air!
DLL extensions make APIs aware,
Build configurations beyond compare! ✨

Pre-merge checks and finishing touches

• 📝 Generate docstrings

Configuration used: Path: .coderabbit.yml

Review profile: CHILL

Plan: Pro

Reviewing files that changed from the base of the PR and between e1b22f1 and 8afe918.

• Lib/test/test_shutil.py is excluded by !Lib/**

• .github/workflows/ci.yaml
• .github/workflows/release.yml
• Cargo.toml
• crates/common/src/fileutils.rs

• Cargo.toml

📄 CodeRabbit inference engine (.github/copilot-instructions.md)

**/*.rs: Follow the default rustfmt code style by running cargo fmt to format Rust code
Always run clippy to lint code (cargo clippy) before completing tasks and fix any warnings or lints introduced by changes
Follow Rust best practices for error handling and memory management
Use the macro system (pyclass, pymodule, pyfunction, etc.) when implementing Python functionality in Rust

Files:

• crates/common/src/fileutils.rs

Learnt from: ShaharNaveh
Repo: RustPython/RustPython PR: 5947
File: .github/workflows/ci.yaml:116-116
Timestamp: 2025-07-11T09:35:43.571Z
Learning: GitHub Actions timeout-minutes field supports expressions that evaluate to integers, such as `${{ contains(matrix.os, 'windows') && 40 || 30 }}`, which will conditionally set different timeout values based on the runner OS.

Applied to files:

• .github/workflows/ci.yaml

Learnt from: ShaharNaveh
Repo: RustPython/RustPython PR: 5947
File: .github/workflows/ci.yaml:116-116
Timestamp: 2025-07-11T09:35:43.571Z
Learning: GitHub Actions supports ternary-like expressions using `&&` and `||` operators in timeout-minutes. The syntax `${{ condition && value_if_true || value_if_false }}` is valid and commonly used, such as `${{ contains(matrix.os, 'windows') && 40 || 30 }}` which evaluates to 40 for Windows runners and 30 for others.

Applied to files:

• .github/workflows/ci.yaml

Learnt from: CR
Repo: RustPython/RustPython PR: 0
File: .github/copilot-instructions.md:0-0
Timestamp: 2025-12-27T14:03:49.034Z
Learning: Applies to **/*.rs : Always run clippy to lint code (`cargo clippy`) before completing tasks and fix any warnings or lints introduced by changes

Applied to files:

• .github/workflows/ci.yaml

Learnt from: arihant2math
Repo: RustPython/RustPython PR: 5790
File: build.rs:2-2
Timestamp: 2025-06-28T16:31:03.991Z
Learning: In Cargo build scripts (build.rs), the environment variable CARGO_CFG_TARGET_OS is guaranteed to exist and is automatically set by Cargo during the build process, making unwrap() safe to use when accessing this variable.

Applied to files:

• .github/workflows/release.yml

• GitHub Check: Run tests under miri
• GitHub Check: Run snippets and cpython tests (ubuntu-latest)
• GitHub Check: Run snippets and cpython tests (macos-latest)
• GitHub Check: Run rust tests (windows-2025)
• GitHub Check: Run snippets and cpython tests (windows-2025)
• GitHub Check: Check Rust code with clippy
• GitHub Check: Run rust tests (macos-latest)
• GitHub Check: Run snippets and cpython tests on wasm-wasi
• GitHub Check: Run rust tests (ubuntu-latest)
• GitHub Check: Check the WASM package and demo
• GitHub Check: Ensure compilation on various targets

.github/workflows/ci.yaml (3)

123-123: Runner update to windows-2025 looks good, contingent on OpenSSL configuration.

The update to windows-2025 aligns with the PR objective to use the preinstalled OpenSSL 3. However, this change depends on the correct OpenSSL environment variable configuration (Lines 110-111).

---

254-254: Runner update to windows-2025 is consistent with rust_tests job.

This change mirrors the runner update in the rust_tests job and is appropriate for the PR objectives.

---

110-111: Verify the OpenSSL paths on the windows-2025 runner to confirm they exist and work with OpenSSL 3.

The target-specific environment variables X86_64_PC_WINDOWS_MSVC_OPENSSL_LIB_DIR and X86_64_PC_WINDOWS_MSVC_OPENSSL_INCLUDE_DIR are a valid approach according to rust-openssl documentation and are preferred over generic OPENSSL_* variables for MSVC targets. However, the specific paths (C:\Program Files\OpenSSL\lib\VC\x64\MD and C:\Program Files\OpenSSL\include) must be verified to exist on the windows-2025 runner with the preinstalled OpenSSL 3, as the directory structure may differ from previous Windows runners.

If these paths are incorrect or the build fails, consider:

• Adding generic OPENSSL_DIR as a fallback, or
• Checking if vcpkg is available as an alternative detection method on windows-2025.

.github/workflows/release.yml (2)

20-21: Verify OpenSSL environment variables match the windows-2025 runner configuration.

These environment variables mirror those added in ci.yaml. The same verification concerns apply here - please ensure the paths are correct for windows-2025 and check if additional environment variables are required per the rust-openssl documentation mentioned in the PR comments.

Refer to the verification steps suggested for ci.yaml (Lines 110-111) to validate these paths.

---

47-47: Runner update to windows-2025 is consistent with CI workflow changes.

This change aligns with the updates in ci.yaml and supports the PR objective to use the preinstalled OpenSSL 3.

crates/common/src/fileutils.rs (1)

306-307: The .dll extension is required for API set loading on Windows — the code is correct.

The Windows loader requires the ".dll" suffix for API set contract names like api-ms-win-core-file-l2-1-4. While API sets are virtual and don't reference actual files on disk, the ".dll" extension is a mandatory loader convention. LoadLibraryW will automatically append ".DLL" if no extension is provided, but explicitly including it (as the code does) is the correct and recommended approach.

Likely an incorrect or invalid review comment.

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