diff --git a/sdks/python/pyproject.toml b/sdks/python/pyproject.toml
index 472a81218..53d823bc6 100644
--- a/sdks/python/pyproject.toml
+++ b/sdks/python/pyproject.toml
@@ -12,7 +12,10 @@ include = ["dropbox_sign/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
-urllib3 = ">= 1.25.3, < 3.0.0"
+urllib3 = [
+  { version = ">= 2.8.0, < 3.0.0", python = ">=3.10" },
+  { version = ">= 1.25.3, < 3.0.0", python = "<3.10" },
+]
 python-dateutil = ">= 2.8.2"
 pydantic = ">= 2"
 typing-extensions = ">= 4.7.1"
diff --git a/sdks/python/requirements.txt b/sdks/python/requirements.txt
index 67f7f68df..c5d71d486 100644
--- a/sdks/python/requirements.txt
+++ b/sdks/python/requirements.txt
@@ -1,4 +1,5 @@
-urllib3 >= 1.25.3, < 3.0.0
+urllib3 >= 2.8.0, < 3.0.0; python_version >= "3.10"
+urllib3 >= 1.25.3, < 3.0.0; python_version < "3.10"
 python_dateutil >= 2.8.2
 pydantic >= 2
 typing-extensions >= 4.7.1
diff --git a/sdks/python/setup.py b/sdks/python/setup.py
index ed66905fd..eafe3b87c 100644
--- a/sdks/python/setup.py
+++ b/sdks/python/setup.py
@@ -26,7 +26,8 @@
 VERSION = "1.11-dev"
 PYTHON_REQUIRES = ">= 3.8"
 REQUIRES = [
-    "urllib3 >= 1.25.3, < 3.0.0",
+    "urllib3 >= 2.8.0, < 3.0.0; python_version >= '3.10'",
+    "urllib3 >= 1.25.3, < 3.0.0; python_version < '3.10'",
     "python-dateutil >= 2.8.2",
     "pydantic >= 2",
     "typing-extensions >= 4.7.1",
diff --git a/sdks/python/templates/README_onlypackage.mustache b/sdks/python/templates/README_onlypackage.mustache
index 2b8bd82e1..f01667685 100644
--- a/sdks/python/templates/README_onlypackage.mustache
+++ b/sdks/python/templates/README_onlypackage.mustache
@@ -26,7 +26,12 @@ This python library package is generated without supporting files like setup.py
 
 To be able to use it, you will need these dependencies in your own package that uses this library:
 
+{{^useCustomTemplateCode}}
 * urllib3 >= 1.25.3, < 3.0.0
+{{/useCustomTemplateCode}}
+{{#useCustomTemplateCode}}
+* urllib3 >= 2.8.0, < 3.0.0 (Python 3.10+) or >= 1.25.3, < 3.0.0 (Python 3.8 and 3.9)
+{{/useCustomTemplateCode}}
 * python-dateutil >= 2.8.2
 {{#asyncio}}
 * aiohttp >= 3.8.4
diff --git a/sdks/python/templates/pyproject.mustache b/sdks/python/templates/pyproject.mustache
index 8dab7dec7..5539d1468 100644
--- a/sdks/python/templates/pyproject.mustache
+++ b/sdks/python/templates/pyproject.mustache
@@ -12,7 +12,15 @@ include = ["{{packageName}}/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
+{{^useCustomTemplateCode}}
 urllib3 = ">= 1.25.3, < 3.0.0"
+{{/useCustomTemplateCode}}
+{{#useCustomTemplateCode}}
+urllib3 = [
+  { version = ">= 2.8.0, < 3.0.0", python = ">=3.10" },
+  { version = ">= 1.25.3, < 3.0.0", python = "<3.10" },
+]
+{{/useCustomTemplateCode}}
 python-dateutil = ">= 2.8.2"
 {{#asyncio}}
 aiohttp = ">= 3.8.4"
diff --git a/sdks/python/templates/requirements.mustache b/sdks/python/templates/requirements.mustache
index 82746ec22..ee1e9efae 100644
--- a/sdks/python/templates/requirements.mustache
+++ b/sdks/python/templates/requirements.mustache
@@ -1,4 +1,10 @@
+{{^useCustomTemplateCode}}
 urllib3 >= 1.25.3, < 3.0.0
+{{/useCustomTemplateCode}}
+{{#useCustomTemplateCode}}
+urllib3 >= 2.8.0, < 3.0.0; python_version >= "3.10"
+urllib3 >= 1.25.3, < 3.0.0; python_version < "3.10"
+{{/useCustomTemplateCode}}
 python_dateutil >= 2.8.2
 {{#asyncio}}
 aiohttp >= 3.8.4
diff --git a/sdks/python/templates/setup.mustache b/sdks/python/templates/setup.mustache
index be7880b0a..1c4359641 100644
--- a/sdks/python/templates/setup.mustache
+++ b/sdks/python/templates/setup.mustache
@@ -17,7 +17,13 @@ NAME = "{{{projectName}}}"
 VERSION = "{{packageVersion}}"
 PYTHON_REQUIRES = ">= 3.8"
 REQUIRES = [
+{{^useCustomTemplateCode}}
     "urllib3 >= 1.25.3, < 3.0.0",
+{{/useCustomTemplateCode}}
+{{#useCustomTemplateCode}}
+    "urllib3 >= 2.8.0, < 3.0.0; python_version >= '3.10'",
+    "urllib3 >= 1.25.3, < 3.0.0; python_version < '3.10'",
+{{/useCustomTemplateCode}}
     "python-dateutil >= 2.8.2",
 {{#asyncio}}
     "aiohttp >= 3.8.4",