diff --git a/requests/sessions.py b/requests/sessions.py
index 631fadb9..2cedaa8f 100644
--- a/requests/sessions.py
+++ b/requests/sessions.py
@@ -696,7 +696,7 @@ class Session(SessionRedirectMixin):
         """
         for (prefix, adapter) in self.adapters.items():
 
-            if url.lower().startswith(prefix):
+            if url.lower().startswith(prefix.lower()):
                 return adapter
 
         # Nothing matches :-/
diff --git a/tests/test_requests.py b/tests/test_requests.py
index 4d399518..05fe63e3 100644
--- a/tests/test_requests.py
+++ b/tests/test_requests.py
@@ -1351,6 +1351,44 @@ class TestRequests:
         assert 'http://' in s2.adapters
         assert 'https://' in s2.adapters
 
+    def test_session_get_adapter_prefix_matching(self, httpbin):
+        prefix = 'https://example.com'
+        more_specific_prefix = prefix + '/some/path'
+
+        url_matching_only_prefix = prefix + '/another/path'
+        url_matching_more_specific_prefix = more_specific_prefix + '/longer/path'
+        url_not_matching_prefix = 'https://another.example.com/'
+
+        s = requests.Session()
+        prefix_adapter = HTTPAdapter()
+        more_specific_prefix_adapter = HTTPAdapter()
+        s.mount(prefix, prefix_adapter)
+        s.mount(more_specific_prefix, more_specific_prefix_adapter)
+
+        assert s.get_adapter(url_matching_only_prefix) is prefix_adapter
+        assert s.get_adapter(url_matching_more_specific_prefix) is more_specific_prefix_adapter
+        assert s.get_adapter(url_not_matching_prefix) not in (prefix_adapter, more_specific_prefix_adapter)
+
+    def test_session_get_adapter_prefix_matching_mixed_case(self, httpbin):
+        mixed_case_prefix = 'hTtPs://eXamPle.CoM/MixEd_CAse_PREfix'
+        url_matching_prefix = mixed_case_prefix + '/full_url'
+
+        s = requests.Session()
+        my_adapter = HTTPAdapter()
+        s.mount(mixed_case_prefix, my_adapter)
+
+        assert s.get_adapter(url_matching_prefix) is my_adapter
+
+    def test_session_get_adapter_prefix_matching_is_case_insensitive(self, httpbin):
+        mixed_case_prefix = 'hTtPs://eXamPle.CoM/MixEd_CAse_PREfix'
+        url_matching_prefix_with_different_case = 'HtTpS://exaMPLe.cOm/MiXeD_caSE_preFIX/another_url'
+
+        s = requests.Session()
+        my_adapter = HTTPAdapter()
+        s.mount(mixed_case_prefix, my_adapter)
+
+        assert s.get_adapter(url_matching_prefix_with_different_case) is my_adapter
+
     def test_header_remove_is_case_insensitive(self, httpbin):
         # From issue #1321
         s = requests.Session()