diff --git a/src/requests/adapters.py b/src/requests/adapters.py
index fc5606bdcb..a0ee292a77 100644
--- a/src/requests/adapters.py
+++ b/src/requests/adapters.py
@@ -8,6 +8,7 @@
 
 import os.path
 import socket  # noqa: F401
+import typing
 
 from urllib3.exceptions import ClosedPoolError, ConnectTimeoutError
 from urllib3.exceptions import HTTPError as _HTTPError
@@ -61,12 +62,44 @@ def SOCKSProxyManager(*args, **kwargs):
         raise InvalidSchema("Missing dependencies for SOCKS support.")
 
 
+if typing.TYPE_CHECKING:
+    from .models import PreparedRequest
+
+
 DEFAULT_POOLBLOCK = False
 DEFAULT_POOLSIZE = 10
 DEFAULT_RETRIES = 0
 DEFAULT_POOL_TIMEOUT = None
 
 
+def _urllib3_request_context(
+    request: "PreparedRequest", verify: "bool | str | None"
+) -> "typing.Dict[str, typing.Any]":
+    context = {}
+    parsed_request_url = urlparse(request.url)
+    scheme = parsed_request_url.scheme.lower()
+    # In case the URL scheme is not entirely lower-case, we need to normalize
+    # that for our dictionary but also for urllib3
+    default_ports = {"http": 80, "https": 443}
+    port = parsed_request_url.port
+    if port is None:
+        port = default_ports.get(scheme)
+    cert_reqs = "CERT_REQUIRED"
+    if verify is False:
+        cert_reqs = "CERT_NONE"
+    if isinstance(verify, str):
+        context["ca_certs"] = verify
+    context.update(
+        {
+            "scheme": scheme,
+            "host": parsed_request_url.hostname,
+            "port": port,
+            "cert_reqs": cert_reqs,
+        }
+    )
+    return context
+
+
 class BaseAdapter:
     """The Base Transport Adapter"""
 
@@ -327,6 +360,28 @@ def build_response(self, req, resp):
 
         return response
 
+    def _get_connection(self, request, verify, proxies=None):
+        # Replace the existing get_connection without breaking things and
+        # ensure that TLS settings are considered when we interact with
+        # urllib3 HTTP Pools
+        proxy = select_proxy(request.url, proxies)
+        urllib3_context = _urllib3_request_context(request, verify)
+        if proxy:
+            proxy = prepend_scheme_if_needed(proxy, "http")
+            proxy_url = parse_url(proxy)
+            if not proxy_url.host:
+                raise InvalidProxyURL(
+                    "Please check proxy URL. It is malformed "
+                    "and could be missing the host."
+                )
+            proxy_manager = self.proxy_manager_for(proxy)
+            conn = proxy_manager.connection_from_context(urllib3_context)
+        else:
+            # Only scheme should be lower case
+            conn = self.poolmanager.connection_from_context(urllib3_context)
+
+        return conn
+
     def get_connection(self, url, proxies=None):
         """Returns a urllib3 connection for the given URL. This should not be
         called from user code, and is only exposed for use when subclassing the
@@ -453,7 +508,7 @@ def send(
         """
 
         try:
-            conn = self.get_connection(request.url, proxies)
+            conn = self._get_connection(request, verify, proxies)
         except LocationValueError as e:
             raise InvalidURL(e, request=request)
 
diff --git a/tests/test_requests.py b/tests/test_requests.py
index 32b5e6700c..d5cc13c79f 100644
--- a/tests/test_requests.py
+++ b/tests/test_requests.py
@@ -2828,6 +2828,13 @@ def test_status_code_425(self):
         assert r5 == 425
         assert r6 == 425
 
+    def test_different_connection_pool_for_tls_settings(self):
+        s = requests.Session()
+        r1 = s.get("https://invalid.badssl.com", verify=False)
+        assert r1.status_code == 421
+        with pytest.raises(requests.exceptions.SSLError):
+            s.get("https://invalid.badssl.com")
+
 
 def test_json_decode_errors_are_serializable_deserializable():
     json_decode_error = requests.exceptions.JSONDecodeError(