diff --git a/mingw-w64-python-cryptography/PKGBUILD b/mingw-w64-python-cryptography/PKGBUILD
index c4c55412bbdad..c74047dda7bcf 100644
--- a/mingw-w64-python-cryptography/PKGBUILD
+++ b/mingw-w64-python-cryptography/PKGBUILD
@@ -3,7 +3,7 @@
 _realname=cryptography
 pkgbase=mingw-w64-python-${_realname}
 pkgname=("${MINGW_PACKAGE_PREFIX}-python-${_realname}")
-pkgver=48.0.1
+pkgver=49.0.0
 pkgrel=1
 pkgdesc="A package designed to expose cryptographic recipes and primitives to Python developers (mingw-w64)"
 arch=('any')
@@ -29,19 +29,39 @@ makedepends=("${MINGW_PACKAGE_PREFIX}-python-build"
              "${MINGW_PACKAGE_PREFIX}-python-maturin"
              "${MINGW_PACKAGE_PREFIX}-rust"
              "${MINGW_PACKAGE_PREFIX}-cc"
-             "${MINGW_PACKAGE_PREFIX}-pkgconf")
+             "${MINGW_PACKAGE_PREFIX}-pkgconf"
+             "git")
 checkdepends=(
               #"${MINGW_PACKAGE_PREFIX}-python-iso8601"
               "${MINGW_PACKAGE_PREFIX}-python-pretend"
               #"${MINGW_PACKAGE_PREFIX}-python-cryptography-vectors"
               "${MINGW_PACKAGE_PREFIX}-python-hypothesis"
               "${MINGW_PACKAGE_PREFIX}-python-pytz")
-source=("https://pypi.org/packages/source/${_realname::1}/${_realname}/${_realname}-${pkgver}.tar.gz")
-sha256sums=('266f4ee051abb2f725b74ef8072b521ce1feacf685a3364fa6a6b45548db791a')
+source=("https://pypi.org/packages/source/${_realname::1}/${_realname}/${_realname}-${pkgver}.tar.gz"
+        "git+https://github.com/PyO3/pyo3#tag=v0.29.0"
+        "pyo3-fix-python-abi-linking.patch")
+sha256sums=('f89660a348f4f78a92366240a61404e337586ef7f5909a2fef59ca88ef505493'
+            '03411beda834ac76b28742d97fc3136bbbcbb4738598fd21633e78301f916e17'
+            '0b815dcb69127b60bd8250df5f5f4f57e94458240bd634cd2c5c6a4823d7b75b')
+
+prepare() {
+  cd "${_realname}-${pkgver}"
+
+  patch -d ../pyo3 -p1 -i ../pyo3-fix-python-abi-linking.patch
+  cat >> Cargo.toml <<END
+
+[patch.crates-io]
+pyo3.path = "../pyo3"
+END
+
+  cargo update -p pyo3
+}
 
 build() {
   cp -r "${_realname}-${pkgver}" "python-build-${MSYSTEM}" && cd "python-build-${MSYSTEM}"
 
+  export OPENSSL_NO_VENDOR=1
+  export PYO3_USE_RAW_DYLIB=0
   export _PYTHON_HOST_PLATFORM=$(python -c "import sysconfig, sys; sys.stdout.write(sysconfig.get_platform())")
   python -m build --wheel --skip-dependency-check --no-isolation
 }
diff --git a/mingw-w64-python-cryptography/pyo3-fix-python-abi-linking.patch b/mingw-w64-python-cryptography/pyo3-fix-python-abi-linking.patch
new file mode 100644
index 0000000000000..b5a35ec909a99
--- /dev/null
+++ b/mingw-w64-python-cryptography/pyo3-fix-python-abi-linking.patch
@@ -0,0 +1,327 @@
+--- a/Cargo.toml
++++ b/Cargo.toml
+@@ -236,7 +236,17 @@ unsafe_op_in_unsafe_fn = "warn"
+ level = "warn"
+ check-cfg = [
+     'cfg(pyo3_disable_reference_pool)',
+-    'cfg(pyo3_leak_on_drop_without_reference_pool)'
++    'cfg(pyo3_leak_on_drop_without_reference_pool)',
++    'cfg(pyo3_use_raw_dylib)',
++    # this horrible hard-coded list should be kept in sync with the list of possible
++    # cfgs in pyo3-ffi/src/impl_/macros.rs
++    #
++    # for library names outside of this set we don't support raw-dylib and require a
++    # proper import library
++    #
++    # maybe in the future this list will not be necessary, see
++    # internals.rust-lang.org/t/support-renames-with-link-name-kind-raw-dylib/24415
++    'cfg(pyo3_dll, values("python3", "python3_d", "python3t", "python3t_d", "python38", "python38_d", "python39", "python39_d", "python310", "python310_d", "python311", "python311_d", "python312", "python312_d", "python313", "python313_d", "python313t", "python313t_d", "python314", "python314_d", "python314t", "python314t_d", "python315", "python315_d", "python315t", "python315t_d", "python316", "python316_d", "python316t", "python316t_d", "libpypy3.11-c"))',
+ ]
+ 
+ 
+--- a/pyo3-build-config/src/impl_.rs
++++ b/pyo3-build-config/src/impl_.rs
+@@ -25,15 +25,6 @@ use crate::{
+ /// Minimum Python version PyO3 supports.
+ pub(crate) const MINIMUM_SUPPORTED_VERSION: PythonVersion = PythonVersion { major: 3, minor: 9 };
+ 
+-pub(crate) const MINIMUM_SUPPORTED_VERSION_PYPY: PythonVersion = PythonVersion {
+-    major: 3,
+-    minor: 11,
+-};
+-pub(crate) const MAXIMUM_SUPPORTED_VERSION_PYPY: PythonVersion = PythonVersion {
+-    major: 3,
+-    minor: 11,
+-};
+-
+ pub(crate) const MINIMUM_SUPPORTED_VERSION_ABI3T: PythonVersion = PythonVersion {
+     major: 3,
+     minor: 15,
+@@ -2314,6 +2305,15 @@ fn default_lib_name_for_target(abi: PythonAbi, target: &Triple) -> String {
+ }
+ 
+ fn default_lib_name_windows(abi: PythonAbi, mingw: bool, debug: bool) -> Result<String> {
++    // mingw formats lib names like unix, and uses a "lib" prefix. We could let the linker
++    // handle "lib" prefix, but that means the `raw-dylib` name is incorrect (where the
++    // "lib" prefix is not automatically added).)
++    if mingw {
++        let mut lib_name = default_lib_name_unix(abi, true, None)?;
++        lib_name.insert_str(0, "lib");
++        return Ok(lib_name);
++    }
++
+     if abi.implementation.is_pypy() {
+         // PyPy on Windows ships `libpypy3.X-c.dll` (e.g. `libpypy3.11-c.dll`),
+         // not CPython's `pythonXY.dll`. With raw-dylib linking we need the real
+@@ -2341,13 +2341,6 @@ fn default_lib_name_windows(abi: PythonAbi, mingw: bool, debug: bool) -> Result<
+             lib_name = lib_name.replace("python3", "python3t");
+         }
+         Ok(lib_name)
+-    } else if mingw {
+-        ensure!(
+-            !abi.kind.is_free_threaded(),
+-            "MinGW free-threaded builds are not currently tested or supported"
+-        );
+-        // https://packages.msys2.org/base/mingw-w64-python
+-        Ok(format!("python{}.{}", abi.version.major, abi.version.minor))
+     } else if abi.kind().is_free_threaded() {
+         #[expect(deprecated, reason = "using constant internally")]
+         {
+@@ -2371,28 +2364,36 @@ fn default_lib_name_windows(abi: PythonAbi, mingw: bool, debug: bool) -> Result<
+     }
+ }
+ 
+-fn default_lib_name_unix(abi: PythonAbi, cygwin: bool, ld_version: Option<&str>) -> Result<String> {
++fn default_lib_name_unix(
++    abi: PythonAbi,
++    use_stable_abi_lib: bool,
++    ld_version: Option<&str>,
++) -> Result<String> {
+     match abi.implementation {
+         PythonImplementation::CPython => match ld_version {
+             Some(ld_version) => Ok(format!("python{ld_version}")),
+-            None => {
+-                if cygwin && matches!(abi.kind, PythonAbiKind::Stable(StableAbi::Abi3)) {
++            None => match abi.kind {
++                PythonAbiKind::Stable(StableAbi::Abi3) if use_stable_abi_lib => {
+                     Ok("python3".to_string())
+-                } else if cygwin && matches!(abi.kind, PythonAbiKind::Stable(StableAbi::Abi3t)) {
++                }
++                PythonAbiKind::Stable(StableAbi::Abi3t) if use_stable_abi_lib => {
+                     Ok("python3t".to_string())
+-                } else if abi.kind.is_free_threaded() {
+-                    #[expect(deprecated, reason = "using constant internally")]
+-                    {
+-                        ensure!(abi.version >= PythonVersion::PY313, "Cannot compile extensions for the free-threaded build on Python versions earlier than 3.13, found {}.{}", abi.version.major, abi.version.minor);
++                }
++                _ => {
++                    if abi.kind.is_free_threaded() {
++                        #[expect(deprecated, reason = "using constant internally")]
++                        {
++                            ensure!(abi.version >= PythonVersion::PY313, "Cannot compile extensions for the free-threaded build on Python versions earlier than 3.13, found {}.{}", abi.version.major, abi.version.minor);
++                        }
++                        Ok(format!(
++                            "python{}.{}t",
++                            abi.version.major, abi.version.minor
++                        ))
++                    } else {
++                        Ok(format!("python{}.{}", abi.version.major, abi.version.minor))
+                     }
+-                    Ok(format!(
+-                        "python{}.{}t",
+-                        abi.version.major, abi.version.minor
+-                    ))
+-                } else {
+-                    Ok(format!("python{}.{}", abi.version.major, abi.version.minor))
+                 }
+-            }
++            },
+         },
+         PythonImplementation::PyPy => match ld_version {
+             Some(ld_version) => Ok(format!("pypy{ld_version}-c")),
+--- a/pyo3-build-config/src/lib.rs
++++ b/pyo3-build-config/src/lib.rs
+@@ -164,34 +164,6 @@ pub fn print_expected_cfgs() {
+     for i in impl_::MINIMUM_SUPPORTED_VERSION.minor..=impl_::STABLE_ABI_MAX_MINOR + 1 {
+         println!("cargo:rustc-check-cfg=cfg(Py_3_{i})");
+     }
+-
+-    // pyo3_dll cfg for raw-dylib linking on Windows
+-    let mut dll_names = vec![
+-        "python3".to_string(),
+-        "python3_d".to_string(),
+-        "python3t".to_string(),
+-        "python3t_d".to_string(),
+-    ];
+-    for i in impl_::MINIMUM_SUPPORTED_VERSION.minor..=impl_::STABLE_ABI_MAX_MINOR + 1 {
+-        dll_names.push(format!("python3{i}"));
+-        dll_names.push(format!("python3{i}_d"));
+-        if i >= 13 {
+-            dll_names.push(format!("python3{i}t"));
+-            dll_names.push(format!("python3{i}t_d"));
+-        }
+-    }
+-    // PyPy DLL names (libpypy3.X-c.dll)
+-    for i in
+-        impl_::MINIMUM_SUPPORTED_VERSION_PYPY.minor..=impl_::MAXIMUM_SUPPORTED_VERSION_PYPY.minor
+-    {
+-        dll_names.push(format!("libpypy3.{i}-c"));
+-    }
+-    let values = dll_names
+-        .iter()
+-        .map(|n| format!("\"{n}\""))
+-        .collect::<Vec<_>>()
+-        .join(", ");
+-    println!("cargo:rustc-check-cfg=cfg(pyo3_dll, values({values}))");
+ }
+ 
+ /// Private exports used in PyO3's build.rs
+--- a/pyo3-ffi/build.rs
++++ b/pyo3-ffi/build.rs
+@@ -191,15 +191,79 @@ fn ensure_target_pointer_width(interpreter_config: &InterpreterConfig) -> Result
+     Ok(())
+ }
+ 
++/// `raw-dylib` currently does not support arbitrary names
++/// (see https://internals.rust-lang.org/t/support-renames-with-link-name-kind-raw-dylib/24415)
++/// so if the lib name is not one of the known subset, we must fall back to full linking.
++fn lib_name_is_known_for_raw_dylib(lib_name: &str) -> bool {
++    // pyo3_dll cfg for raw-dylib linking on Windows
++    if matches!(
++        lib_name,
++        "python3" | "python3_d" | "python3t" | "python3t_d"
++    ) {
++        return true;
++    }
++
++    // support raw-dylib linking for all CPython versions supported, plus the next prerelease
++    for i in SUPPORTED_VERSIONS_CPYTHON.min.minor..=SUPPORTED_VERSIONS_CPYTHON.max.minor + 1 {
++        if lib_name == format!("python3{i}") || lib_name == format!("python3{i}_d") {
++            return true;
++        }
++        if i >= 13 && (lib_name == format!("python3{i}t") || lib_name == format!("python3{i}t_d")) {
++            return true;
++        }
++    }
++    // PyPy DLL names (libpypy3.X-c.dll)
++    for i in SUPPORTED_VERSIONS_PYPY.min.minor..=SUPPORTED_VERSIONS_PYPY.max.minor {
++        if lib_name == format!("libpypy3.{i}-c") {
++            return true;
++        }
++    }
++
++    false
++}
++
++/// Whether to use raw-dylib linking.
++///
++/// Currently, this only applies if all of the following are true:
++/// - The target OS is Windows.
++/// - The Python library name is one of the [known subset][lib_name_is_known_for_raw_dylib].
++/// - The `PYO3_USE_RAW_DYLIB` environment variable is not set, or is set to `1`.
++///
++/// NB in some cases (e.g. mixed C / Rust builds) it might be necessary to link the full Python
++/// library rather than rely on the symbols which PyO3 defines as raw-dylib, which is why
++/// we have the opt-out env var.
++fn should_use_raw_dylib_linking(lib_name: &str) -> bool {
++    let target_os = cargo_env_var("CARGO_CFG_TARGET_OS").unwrap();
++    if target_os != "windows" {
++        return false;
++    }
++
++    match (
++        lib_name_is_known_for_raw_dylib(lib_name),
++        env_var("PYO3_USE_RAW_DYLIB"),
++    ) {
++        (true, None) => true,
++        (true, Some(os_str)) if os_str == "1" => true,
++        (false, Some(os_str)) if os_str == "1" => {
++            warn!(
++                "PYO3_USE_RAW_DYLIB is set to 1 but the Python library name is not recognized. \
++                Falling back to full linking."
++            );
++            false
++        }
++        _ => false,
++    }
++}
++
+ fn emit_link_config(build_config: &BuildConfig) -> Result<()> {
+-    let interpreter_config = &build_config.interpreter_config;
+     let target_os = cargo_env_var("CARGO_CFG_TARGET_OS").unwrap();
++    let interpreter_config = &build_config.interpreter_config;
+ 
+     let lib_name = interpreter_config
+         .lib_name()
+         .ok_or("attempted to link to Python shared library but config does not contain lib_name")?;
+ 
+-    if target_os == "windows" {
++    if should_use_raw_dylib_linking(lib_name) {
+         // Use raw-dylib linking: emit a cfg so that `extern_libpython!` picks the
+         // right `#[link(name = "...", kind = "raw-dylib")]` attribute at compile time.
+         // This eliminates the need for import libraries (.lib files) entirely.
+@@ -207,27 +271,36 @@ fn emit_link_config(build_config: &BuildConfig) -> Result<()> {
+         // Note: raw-dylib is inherently dynamic linking. Static embedding of the
+         // Python interpreter on Windows is not supported by this path (and is not
+         // officially supported by CPython on Windows).
++        println!("cargo:rustc-cfg=pyo3_use_raw_dylib");
+         println!("cargo:rustc-cfg=pyo3_dll=\"{lib_name}\"");
+-    } else {
+-        println!(
+-            "cargo:rustc-link-lib={link_model}{lib_name}",
+-            link_model = if interpreter_config.shared() {
+-                ""
+-            } else {
+-                "static="
+-            },
+-        );
++        return Ok(());
++    }
+ 
+-        if let Some(lib_dir) = interpreter_config.lib_dir() {
+-            println!("cargo:rustc-link-search=native={lib_dir}");
+-        } else if matches!(build_config.source, BuildConfigSource::CrossCompile) {
+-            warn!(
+-                "The output binary will link to libpython, \
+-                but PYO3_CROSS_LIB_DIR environment variable is not set. \
+-                Ensure that the target Python library directory is \
+-                in the rustc native library search path."
+-            );
++    println!(
++        "cargo:rustc-link-lib={link_model}{alias}{lib_name}",
++        link_model = if interpreter_config.shared() {
++            ""
++        } else {
++            "static="
++        },
++        // on windows we emit `#[link(name = "pythonXY")]` attributes
++        // and need this alias here to get the right name for the final link
++        alias = if target_os == "windows" {
++            "pythonXY:"
++        } else {
++            ""
+         }
++    );
++
++    if let Some(lib_dir) = interpreter_config.lib_dir() {
++        println!("cargo:rustc-link-search=native={lib_dir}");
++    } else if matches!(build_config.source, BuildConfigSource::CrossCompile) {
++        warn!(
++            "The output binary will link to libpython, \
++            but PYO3_CROSS_LIB_DIR environment variable is not set. \
++            Ensure that the target Python library directory is \
++            in the rustc native library search path."
++        );
+     }
+ 
+     Ok(())
+--- a/pyo3-ffi/src/impl_/macros.rs
++++ b/pyo3-ffi/src/impl_/macros.rs
+@@ -268,10 +268,12 @@ macro_rules! extern_libpython {
+             "python313", "python313_d",
+             "python314", "python314_d",
+             "python315", "python315_d",
++            "python316", "python316_d",
+             // free-threaded builds (3.13+)
+             "python313t", "python313t_d",
+             "python314t", "python314t_d",
+             "python315t", "python315t_d",
++            "python316t", "python316t_d",
+             // PyPy (DLL is libpypy3.X-c.dll, not pythonXY.dll)
+             "libpypy3.11-c",
+         );
+@@ -286,11 +288,12 @@ macro_rules! extern_libpython {
+     // separate cfg_attr arms per architecture.
+     (@impl $abi:literal { $($body:tt)* } $($dll:literal),* $(,)?) => {
+         $(
+-            #[cfg_attr(all(windows, target_arch = "x86", pyo3_dll = $dll),
++            #[cfg_attr(all(windows, pyo3_use_raw_dylib, target_arch = "x86", pyo3_dll = $dll),
+                 link(name = $dll, kind = "raw-dylib", import_name_type = "undecorated"))]
+-            #[cfg_attr(all(windows, not(target_arch = "x86"), pyo3_dll = $dll),
++            #[cfg_attr(all(windows, pyo3_use_raw_dylib, not(target_arch = "x86"), pyo3_dll = $dll),
+                 link(name = $dll, kind = "raw-dylib"))]
+         )*
++        #[cfg_attr(all(windows, not(pyo3_use_raw_dylib)), link(name = "pythonXY"))]
+         extern $abi {
+             extern_libpython_items! { $($body)* }
+         }
diff --git a/mingw-w64-python-pyopenssl/PKGBUILD b/mingw-w64-python-pyopenssl/PKGBUILD
index 1252f6d6c1e9b..08c07c8e5507a 100644
--- a/mingw-w64-python-pyopenssl/PKGBUILD
+++ b/mingw-w64-python-pyopenssl/PKGBUILD
@@ -3,7 +3,7 @@
 _realname=pyopenssl
 pkgbase=mingw-w64-python-${_realname}
 pkgname=("${MINGW_PACKAGE_PREFIX}-python-${_realname}")
-pkgver=26.2.0
+pkgver=26.3.0
 pkgrel=1
 pkgdesc="Python wrapper module around the OpenSSL library (mingw-w64)"
 arch=('any')
@@ -26,7 +26,7 @@ makedepends=("${MINGW_PACKAGE_PREFIX}-python-build"
              "${MINGW_PACKAGE_PREFIX}-python-setuptools")
 checkdepends=("${MINGW_PACKAGE_PREFIX}-python-pytest")
 source=("https://pypi.org/packages/source/${_realname::1}/${_realname}/${_realname}-${pkgver}.tar.gz")
-sha256sums=('8c6fcecd1183a7fc897548dfe388b0cdb7f37e018200d8409cf33959dbe35387')
+sha256sums=('589de7fae1c9ea670d18422ed00fc04da787bbde8e1454aea872aa57b49ad341')
 
 build() {
   cp -r "${_realname}-${pkgver}" "python-build-${MSYSTEM}" && cd "python-build-${MSYSTEM}"