diff --git a/news/truststore.vendor.rst b/news/truststore.vendor.rst
new file mode 100644
index 00000000000..f8ce27e4b32
--- /dev/null
+++ b/news/truststore.vendor.rst
@@ -0,0 +1 @@
+Upgrade truststore to 0.10.1
diff --git a/src/pip/_vendor/truststore/__init__.py b/src/pip/_vendor/truststore/__init__.py
index e468bf8cebd..cdff8143feb 100644
--- a/src/pip/_vendor/truststore/__init__.py
+++ b/src/pip/_vendor/truststore/__init__.py
@@ -7,7 +7,7 @@
 
 # Detect Python runtimes which don't implement SSLObject.get_unverified_chain() API
 # This API only became public in Python 3.13 but was available in CPython and PyPy since 3.10.
-if _sys.version_info < (3, 13):
+if _sys.version_info < (3, 13) and _sys.implementation.name not in ("cpython", "pypy"):
     try:
         import ssl as _ssl
     except ImportError:
@@ -33,4 +33,4 @@
 del _api, _sys  # type: ignore[name-defined] # noqa: F821
 
 __all__ = ["SSLContext", "inject_into_ssl", "extract_from_ssl"]
-__version__ = "0.10.0"
+__version__ = "0.10.1"
diff --git a/src/pip/_vendor/truststore/_api.py b/src/pip/_vendor/truststore/_api.py
index aeb023af756..2c0ce196a36 100644
--- a/src/pip/_vendor/truststore/_api.py
+++ b/src/pip/_vendor/truststore/_api.py
@@ -5,7 +5,7 @@
 import sys
 import typing
 
-import _ssl  # type: ignore[import-not-found]
+import _ssl
 
 from ._ssl_constants import (
     _original_SSLContext,
@@ -43,6 +43,23 @@ def inject_into_ssl() -> None:
     except ImportError:
         pass
 
+    # requests starting with 2.32.0 added a preloaded SSL context to improve concurrent performance;
+    # this unfortunately leads to a RecursionError, which can be avoided by patching the preloaded SSL context with
+    # the truststore patched instance
+    # also see https://github.com/psf/requests/pull/6667
+    try:
+        from pip._vendor.requests import adapters as requests_adapters
+
+        preloaded_context = getattr(requests_adapters, "_preloaded_ssl_context", None)
+        if preloaded_context is not None:
+            setattr(
+                requests_adapters,
+                "_preloaded_ssl_context",
+                SSLContext(ssl.PROTOCOL_TLS_CLIENT),
+            )
+    except ImportError:
+        pass
+
 
 def extract_from_ssl() -> None:
     """Restores the :class:`ssl.SSLContext` class to its original state"""
diff --git a/src/pip/_vendor/vendor.txt b/src/pip/_vendor/vendor.txt
index f04a9c1e73c..4a1933596b6 100644
--- a/src/pip/_vendor/vendor.txt
+++ b/src/pip/_vendor/vendor.txt
@@ -15,4 +15,4 @@ rich==13.9.4
 resolvelib==1.0.1
 setuptools==70.3.0
 tomli==2.2.1
-truststore==0.10.0
+truststore==0.10.1
diff --git a/tools/vendoring/patches/truststore.patch b/tools/vendoring/patches/truststore.patch
new file mode 100644
index 00000000000..d8d6351d9d4
--- /dev/null
+++ b/tools/vendoring/patches/truststore.patch
@@ -0,0 +1,20 @@
+diff --git a/src/pip/_vendor/truststore/_api.py b/src/pip/_vendor/truststore/_api.py
+index 47b7a63ab..d09d3096f 100644
+--- a/src/pip/_vendor/truststore/_api.py
++++ b/src/pip/_vendor/truststore/_api.py
+@@ -48,12 +48,12 @@ def inject_into_ssl() -> None:
+     # the truststore patched instance
+     # also see https://github.com/psf/requests/pull/6667
+     try:
+-        import requests.adapters
++        from pip._vendor.requests import adapters as requests_adapters
+
+-        preloaded_context = getattr(requests.adapters, "_preloaded_ssl_context", None)
++        preloaded_context = getattr(requests_adapters, "_preloaded_ssl_context", None)
+         if preloaded_context is not None:
+             setattr(
+-                requests.adapters,
++                requests_adapters,
+                 "_preloaded_ssl_context",
+                 SSLContext(ssl.PROTOCOL_TLS_CLIENT),
+             )