diff --git a/pyproject.toml b/pyproject.toml
index bca19b2d1..22220fa0e 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -141,7 +141,7 @@ dev = [
     # URLLib3 version 2.x doesn't play well with the version of pytest-vcr that supports
     # Python 3.9 and lower.  This can be removed once 3.9 goes EOS or when we stop using
     # VCR for the test suite.
-    "urllib3==1.26.20",
+    "urllib3==2.7.0",
     "rich>=13.8.1",
     "ptpython>=3.0.29",
     "typer>=0.20.0",
diff --git a/uv.lock b/uv.lock
index f809f08aa..f91e3b77c 100644
--- a/uv.lock
+++ b/uv.lock
@@ -761,7 +761,7 @@ name = "exceptiongroup"
 version = "1.3.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "typing-extensions", marker = "python_full_version < '3.13'" },
+    { name = "typing-extensions", marker = "python_full_version < '3.11'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/50/79/66800aadf48771f6b62f7eb014e352e5d06856655206165d775e675a02c9/exceptiongroup-1.3.1.tar.gz", hash = "sha256:8b412432c6055b0b7d14c310000ae93352ed6754f70fa8f7c34141f91c4e3219", size = 30371, upload-time = "2025-11-21T23:01:54.787Z" }
 wheels = [
@@ -1827,7 +1827,7 @@ dev = [
     { name = "rich", specifier = ">=13.8.1" },
     { name = "ruff", specifier = ">=0.6.4" },
     { name = "typer", specifier = ">=0.20.0" },
-    { name = "urllib3", specifier = "==1.26.20" },
+    { name = "urllib3", specifier = "==2.7.0" },
 ]
 docs = [
     { name = "autodoc-pydantic", specifier = ">=2.2.0" },
@@ -2356,11 +2356,11 @@ wheels = [
 
 [[package]]
 name = "urllib3"
-version = "1.26.20"
+version = "2.7.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/e4/e8/6ff5e6bc22095cfc59b6ea711b687e2b7ed4bdb373f7eeec370a97d7392f/urllib3-1.26.20.tar.gz", hash = "sha256:40c2dc0c681e47eb8f90e7e27bf6ff7df2e677421fd46756da1161c39ca70d32", size = 307380, upload-time = "2024-08-29T15:43:11.37Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/53/0c/06f8b233b8fd13b9e5ee11424ef85419ba0d8ba0b3138bf360be2ff56953/urllib3-2.7.0.tar.gz", hash = "sha256:231e0ec3b63ceb14667c67be60f2f2c40a518cb38b03af60abc813da26505f4c", size = 433602, upload-time = "2026-05-07T16:13:18.596Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/33/cf/8435d5a7159e2a9c83a95896ed596f68cf798005fe107cc655b5c5c14704/urllib3-1.26.20-py2.py3-none-any.whl", hash = "sha256:0ed14ccfbf1c30a9072c7ca157e4319b70d65f623e91e7b32fadb2853431016e", size = 144225, upload-time = "2024-08-29T15:43:08.921Z" },
+    { url = "https://files.pythonhosted.org/packages/7f/3e/5db95bcf282c52709639744ca2a8b149baccf648e39c8cc87553df9eae0c/urllib3-2.7.0-py3-none-any.whl", hash = "sha256:9fb4c81ebbb1ce9531cce37674bbc6f1360472bc18ca9a553ede278ef7276897", size = 131087, upload-time = "2026-05-07T16:13:17.151Z" },
 ]
 
 [[package]]