diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index 607ed6c..469005a 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -12,12 +12,16 @@ jobs:
           '3.11',
           '3.12',
         ]
-    name: Python ${{ matrix.python-version }}
+        pip-override: [
+          '',
+          'pip install "urllib3<2"',
+        ]
+    name: Python ${{ matrix.python-version }} ${{ matrix.pip-override }}
     steps:
     - uses: actions/checkout@v4
     - uses: actions/setup-python@v5
       with:
         python-version: ${{ matrix.python-version }}
         architecture: x64
-    - run: make test
+    - run: make test PIP_OVERRIDES='${{ matrix.pip-override }}'
     - run: make lint
diff --git a/Makefile b/Makefile
index ca7a773..90273fb 100644
--- a/Makefile
+++ b/Makefile
@@ -7,6 +7,7 @@ venv-tools: requirements.tools.txt
 	rm -rf venv-tools
 	python3 -m venv venv-tools
 	venv-tools/bin/pip install -r requirements.tools.txt
+	${PIP_OVERRIDES}
 
 .PHONY: clean
 clean:
diff --git a/flareio/api_client.py b/flareio/api_client.py
index 290e099..8d551df 100644
--- a/flareio/api_client.py
+++ b/flareio/api_client.py
@@ -47,18 +47,23 @@ def _create_session() -> requests.Session:
             ),
         )
 
+        retry = Retry(
+            total=5,
+            backoff_factor=2,
+            status_forcelist=[429, 502, 503, 504],
+            allowed_methods={"GET", "POST"},
+        )
+
+        # Support for urllib3 < 2.X
+        if hasattr(Retry, "backoff_max"):
+            retry.backoff_max = 15
+        
+        retry.backoff_max = 15
+
         # Enable retries
         session.mount(
             "https://",
-            HTTPAdapter(
-                max_retries=Retry(
-                    total=5,
-                    backoff_factor=2,
-                    status_forcelist=[429, 502, 503, 504],
-                    allowed_methods={"GET", "POST"},
-                    backoff_max=15,
-                )
-            ),
+            HTTPAdapter(max_retries=retry),
         )
 
         return session