diff --git a/thousandeyes-sdk-administrative/pyproject.toml b/thousandeyes-sdk-administrative/pyproject.toml
index 5bbf4219..434a935a 100644
--- a/thousandeyes-sdk-administrative/pyproject.toml
+++ b/thousandeyes-sdk-administrative/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Administrative API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-agents/pyproject.toml b/thousandeyes-sdk-agents/pyproject.toml
index 74f2714d..b873f3fa 100644
--- a/thousandeyes-sdk-agents/pyproject.toml
+++ b/thousandeyes-sdk-agents/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Agents API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-alerts/pyproject.toml b/thousandeyes-sdk-alerts/pyproject.toml
index 4dec8053..339c1421 100644
--- a/thousandeyes-sdk-alerts/pyproject.toml
+++ b/thousandeyes-sdk-alerts/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Alerts API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-bgp-monitors/pyproject.toml b/thousandeyes-sdk-bgp-monitors/pyproject.toml
index 6b2e20f9..bce30389 100644
--- a/thousandeyes-sdk-bgp-monitors/pyproject.toml
+++ b/thousandeyes-sdk-bgp-monitors/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK BGP Monitors API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-connectors/pyproject.toml b/thousandeyes-sdk-connectors/pyproject.toml
index c06761cc..107f0ba7 100644
--- a/thousandeyes-sdk-connectors/pyproject.toml
+++ b/thousandeyes-sdk-connectors/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Integrations API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-core/pyproject.toml b/thousandeyes-sdk-core/pyproject.toml
index a40bd17c..fd54435e 100644
--- a/thousandeyes-sdk-core/pyproject.toml
+++ b/thousandeyes-sdk-core/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Core"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-core/src/thousandeyes_sdk/core/thousandeyes_retry.py b/thousandeyes-sdk-core/src/thousandeyes_sdk/core/thousandeyes_retry.py
index ecc8d90f..4427020f 100644
--- a/thousandeyes-sdk-core/src/thousandeyes_sdk/core/thousandeyes_retry.py
+++ b/thousandeyes-sdk-core/src/thousandeyes_sdk/core/thousandeyes_retry.py
@@ -48,11 +48,12 @@ class ThousandEyesRetry(Retry):
             history: Optional[tuple[RequestHistory, ...]] = None,
             respect_retry_after_header: bool = True,
             remove_headers_on_redirect: Collection[str] = Retry.DEFAULT_REMOVE_HEADERS_ON_REDIRECT,
-            backoff_jitter: float = 0.0) -> None:
+            backoff_jitter: float = 0.0,
+            retry_after_max: int = Retry.DEFAULT_RETRY_AFTER_MAX) -> None:
         super().__init__(total, connect, read, redirect, status, other, allowed_methods,
                          status_forcelist, backoff_factor, backoff_max, raise_on_redirect,
                          raise_on_status, history, respect_retry_after_header,
-                         remove_headers_on_redirect, backoff_jitter)
+                         remove_headers_on_redirect, backoff_jitter, retry_after_max)
 
     def is_retry(self, method: str, status_code: int, has_retry_after: bool = False) -> bool:
         # Always retry on 429, regardless of method or status_forcelist
diff --git a/thousandeyes-sdk-core/test/test_thousandeyes_retry.py b/thousandeyes-sdk-core/test/test_thousandeyes_retry.py
index 944e5dd6..a3e460ff 100644
--- a/thousandeyes-sdk-core/test/test_thousandeyes_retry.py
+++ b/thousandeyes-sdk-core/test/test_thousandeyes_retry.py
@@ -41,3 +41,19 @@ def test_parse_reset_header_invalid():
     retry = ThousandEyesRetry()
     assert retry._parse_reset_header("invalid") is None
     assert retry._parse_reset_header(None) is None
+
+
+def test_retry_new_clones_with_retry_after_max():
+    retry = ThousandEyesRetry(retry_after_max=3600)
+    cloned = retry.new()
+    assert isinstance(cloned, ThousandEyesRetry)
+    assert cloned.retry_after_max == 3600
+
+
+def test_retry_increment_on_429():
+    response = Mock(spec=HTTPResponse)
+    response.status = 429
+    response.headers = {"Retry-After": "0"}
+    retry = ThousandEyesRetry(total=1)
+    new_retry = retry.increment(method="GET", url="/test", response=response)
+    assert isinstance(new_retry, ThousandEyesRetry)
diff --git a/thousandeyes-sdk-credentials/pyproject.toml b/thousandeyes-sdk-credentials/pyproject.toml
index c71e1e9c..fa9816e7 100644
--- a/thousandeyes-sdk-credentials/pyproject.toml
+++ b/thousandeyes-sdk-credentials/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Credentials API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-dashboards/pyproject.toml b/thousandeyes-sdk-dashboards/pyproject.toml
index b6433f3f..c95fbaee 100644
--- a/thousandeyes-sdk-dashboards/pyproject.toml
+++ b/thousandeyes-sdk-dashboards/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Dashboards API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-emulation/pyproject.toml b/thousandeyes-sdk-emulation/pyproject.toml
index 82b9233a..73e420bd 100644
--- a/thousandeyes-sdk-emulation/pyproject.toml
+++ b/thousandeyes-sdk-emulation/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Emulation API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-endpoint-agents/pyproject.toml b/thousandeyes-sdk-endpoint-agents/pyproject.toml
index 1e72dee5..b9968a4f 100644
--- a/thousandeyes-sdk-endpoint-agents/pyproject.toml
+++ b/thousandeyes-sdk-endpoint-agents/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Endpoint Agents API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-endpoint-instant-tests/pyproject.toml b/thousandeyes-sdk-endpoint-instant-tests/pyproject.toml
index 17cce6de..ba8fc57a 100644
--- a/thousandeyes-sdk-endpoint-instant-tests/pyproject.toml
+++ b/thousandeyes-sdk-endpoint-instant-tests/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Endpoint Instant Scheduled Tests API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-endpoint-labels/pyproject.toml b/thousandeyes-sdk-endpoint-labels/pyproject.toml
index 4ba71702..fbf91687 100644
--- a/thousandeyes-sdk-endpoint-labels/pyproject.toml
+++ b/thousandeyes-sdk-endpoint-labels/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Endpoint Agent Labels API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-endpoint-test-results/pyproject.toml b/thousandeyes-sdk-endpoint-test-results/pyproject.toml
index 88b8cf54..56d42c98 100644
--- a/thousandeyes-sdk-endpoint-test-results/pyproject.toml
+++ b/thousandeyes-sdk-endpoint-test-results/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Endpoint Test Results API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-endpoint-tests/pyproject.toml b/thousandeyes-sdk-endpoint-tests/pyproject.toml
index 47478ebf..dd0fd6d5 100644
--- a/thousandeyes-sdk-endpoint-tests/pyproject.toml
+++ b/thousandeyes-sdk-endpoint-tests/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Endpoint Tests API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-event-detection/pyproject.toml b/thousandeyes-sdk-event-detection/pyproject.toml
index 437c1490..4be216e4 100644
--- a/thousandeyes-sdk-event-detection/pyproject.toml
+++ b/thousandeyes-sdk-event-detection/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Event Detection API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-instant-tests/pyproject.toml b/thousandeyes-sdk-instant-tests/pyproject.toml
index f10d50ad..a0b3eeb7 100644
--- a/thousandeyes-sdk-instant-tests/pyproject.toml
+++ b/thousandeyes-sdk-instant-tests/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Instant Tests API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-internet-insights/pyproject.toml b/thousandeyes-sdk-internet-insights/pyproject.toml
index 12f3b7c8..7ccbcc6e 100644
--- a/thousandeyes-sdk-internet-insights/pyproject.toml
+++ b/thousandeyes-sdk-internet-insights/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Internet Insights API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-snapshots/pyproject.toml b/thousandeyes-sdk-snapshots/pyproject.toml
index 8f4e0a9c..97814c18 100644
--- a/thousandeyes-sdk-snapshots/pyproject.toml
+++ b/thousandeyes-sdk-snapshots/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Test Snapshots API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-streaming/pyproject.toml b/thousandeyes-sdk-streaming/pyproject.toml
index 3d9f3c18..959b0e84 100644
--- a/thousandeyes-sdk-streaming/pyproject.toml
+++ b/thousandeyes-sdk-streaming/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK ThousandEyes for OpenTelemetry API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-tags/pyproject.toml b/thousandeyes-sdk-tags/pyproject.toml
index 94402d71..0bea620a 100644
--- a/thousandeyes-sdk-tags/pyproject.toml
+++ b/thousandeyes-sdk-tags/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Tags API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-test-results/pyproject.toml b/thousandeyes-sdk-test-results/pyproject.toml
index c4489116..c17ca9a7 100644
--- a/thousandeyes-sdk-test-results/pyproject.toml
+++ b/thousandeyes-sdk-test-results/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Test Results API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-tests/pyproject.toml b/thousandeyes-sdk-tests/pyproject.toml
index 5310e17e..d21ad89d 100644
--- a/thousandeyes-sdk-tests/pyproject.toml
+++ b/thousandeyes-sdk-tests/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Tests API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",
diff --git a/thousandeyes-sdk-usage/pyproject.toml b/thousandeyes-sdk-usage/pyproject.toml
index e3fe5004..cbf058f8 100644
--- a/thousandeyes-sdk-usage/pyproject.toml
+++ b/thousandeyes-sdk-usage/pyproject.toml
@@ -9,7 +9,7 @@ description = "ThousandEyes SDK Usage API"
 license = { file = "LICENSE" }
 requires-python = ">= 3.8"
 dependencies = [
-    "urllib3 >= 2.0.0",
+    "urllib3 >= 2.6.3",
     "python-dateutil >=2.8.2",
     "pydantic >=2.1.0",
     "typing-extensions >=4.7.1",