diff --git a/jira/resilientsession.py b/jira/resilientsession.py
index 39ce7643d..4cf7cfb8e 100644
--- a/jira/resilientsession.py
+++ b/jira/resilientsession.py
@@ -188,6 +188,18 @@ def _jira_prepare(self, **original_kwargs) -> dict:
         if "verify" not in prepared_kwargs:
             prepared_kwargs["verify"] = self.verify
 
+        if "proxies" not in prepared_kwargs and self.proxies:
+            # Session.request() only falls back to self.proxies when no
+            # "proxies" kwarg is passed at all, but by then
+            # merge_environment_settings() has already used setdefault() to
+            # fill an empty request-level proxies dict from the http_proxy/
+            # https_proxy environment variables, and merge_setting() let's
+            # that request-level dict win over self.proxies for any matching
+            # key. Passing self.proxies through explicitly here means it's
+            # already populated before the environment fallback runs, so it
+            # can only fill in gaps rather than being overridden by them.
+            prepared_kwargs["proxies"] = self.proxies
+
         return prepared_kwargs
 
     def request(  # type: ignore[override] # An intentionally different override
diff --git a/tests/test_resilientsession.py b/tests/test_resilientsession.py
index 2d0ed9047..f23c917d1 100644
--- a/tests/test_resilientsession.py
+++ b/tests/test_resilientsession.py
@@ -254,3 +254,30 @@ def test_empty_dict_body_not_forwarded(mocked_request_method: Mock):
     session.get(url="mocked_url", data={})
     kwargs = mocked_request_method.call_args.kwargs
     assert kwargs.get("data") == {}
+
+
+@patch("requests.Session.request")
+def test_configured_proxies_are_forwarded(mocked_request_method: Mock):
+    # Disable retries for this test.
+    session = jira.resilientsession.ResilientSession(max_retries=0)
+    # A user-configured session proxy must be passed explicitly as the
+    # per-request "proxies" kwarg. Left unset, requests.Session.request()
+    # let's an env-derived http_proxy/https_proxy value (from
+    # merge_environment_settings()'s setdefault()) win over self.proxies
+    # for any matching key.
+    session.proxies = {
+        "http": "http://localhost:3128",
+        "https": "http://localhost:3128",
+    }
+    session.get(url="mocked_url")
+    kwargs = mocked_request_method.call_args.kwargs
+    assert kwargs.get("proxies") == session.proxies
+
+
+@patch("requests.Session.request")
+def test_no_proxies_kwarg_when_unconfigured(mocked_request_method: Mock):
+    # Disable retries for this test.
+    session = jira.resilientsession.ResilientSession(max_retries=0)
+    session.get(url="mocked_url")
+    kwargs = mocked_request_method.call_args.kwargs
+    assert "proxies" not in kwargs