diff --git a/pyproject.toml b/pyproject.toml
index 85f5925..a0545f3 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -42,6 +42,11 @@ dev = [
     "types-pyyaml>=6.0.0",
 ]
 
+[tool.uv]
+constraint-dependencies = [
+    "urllib3<2.7; python_full_version < '3.10'",
+]
+
 [project.scripts]
 promptfoo = "promptfoo.cli:main"
 
diff --git a/uv.lock b/uv.lock
index 69962ed..1b4a939 100644
--- a/uv.lock
+++ b/uv.lock
@@ -6,6 +6,12 @@ resolution-markers = [
     "python_full_version < '3.10'",
 ]
 
+[options]
+exclude-newer = "2026-05-11T01:34:42Z"
+
+[manifest]
+constraints = [{ name = "urllib3", marker = "python_full_version < '3.10'", specifier = "<2.7" }]
+
 [[package]]
 name = "backoff"
 version = "2.2.1"
@@ -601,7 +607,8 @@ dependencies = [
     { name = "certifi" },
     { name = "charset-normalizer" },
     { name = "idna" },
-    { name = "urllib3" },
+    { name = "urllib3", version = "2.6.3", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version < '3.10'" },
+    { name = "urllib3", version = "2.7.0", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version >= '3.10'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/c9/74/b3ff8e6c8446842c3f5c837e9c3dfcfe2018ea6ecef224c710c85ef728f4/requests-2.32.5.tar.gz", hash = "sha256:dbba0bac56e100853db0ea71b82b4dfd5fe2bf6d3754a8893c3af500cec7d7cf", size = 134517, upload-time = "2025-08-18T20:46:02.573Z" }
 wheels = [
@@ -714,7 +721,22 @@ wheels = [
 name = "urllib3"
 version = "2.6.3"
 source = { registry = "https://pypi.org/simple" }
+resolution-markers = [
+    "python_full_version < '3.10'",
+]
 sdist = { url = "https://files.pythonhosted.org/packages/c7/24/5f1b3bdffd70275f6661c76461e25f024d5a38a46f04aaca912426a2b1d3/urllib3-2.6.3.tar.gz", hash = "sha256:1b62b6884944a57dbe321509ab94fd4d3b307075e0c2eae991ac71ee15ad38ed", size = 435556, upload-time = "2026-01-07T16:24:43.925Z" }
 wheels = [
     { url = "https://files.pythonhosted.org/packages/39/08/aaaad47bc4e9dc8c725e68f9d04865dbcb2052843ff09c97b08904852d84/urllib3-2.6.3-py3-none-any.whl", hash = "sha256:bf272323e553dfb2e87d9bfd225ca7b0f467b919d7bbd355436d3fd37cb0acd4", size = 131584, upload-time = "2026-01-07T16:24:42.685Z" },
 ]
+
+[[package]]
+name = "urllib3"
+version = "2.7.0"
+source = { registry = "https://pypi.org/simple" }
+resolution-markers = [
+    "python_full_version >= '3.10'",
+]
+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/7f/3e/5db95bcf282c52709639744ca2a8b149baccf648e39c8cc87553df9eae0c/urllib3-2.7.0-py3-none-any.whl", hash = "sha256:9fb4c81ebbb1ce9531cce37674bbc6f1360472bc18ca9a553ede278ef7276897", size = 131087, upload-time = "2026-05-07T16:13:17.151Z" },
+]