diff --git a/homeassistant/package_constraints.txt b/homeassistant/package_constraints.txt
index 3ce056e1a46..17f114b99ce 100644
--- a/homeassistant/package_constraints.txt
+++ b/homeassistant/package_constraints.txt
@@ -59,7 +59,9 @@ zeroconf==0.71.4
 pycryptodome>=3.6.6
 
 # Constrain urllib3 to ensure we deal with CVE-2020-26137 and CVE-2021-33503
-urllib3>=1.26.5
+# Temporary setting an upper bound, to prevent compat issues with urllib3>=2
+# https://github.com/home-assistant/core/issues/97248
+urllib3>=1.26.5,<2
 
 # Constrain httplib2 to protect against GHSA-93xj-8mrv-444m
 # https://github.com/advisories/GHSA-93xj-8mrv-444m
diff --git a/script/gen_requirements_all.py b/script/gen_requirements_all.py
index 02d528c33e2..b2954dc777b 100755
--- a/script/gen_requirements_all.py
+++ b/script/gen_requirements_all.py
@@ -61,7 +61,9 @@ CONSTRAINT_BASE = """
 pycryptodome>=3.6.6
 
 # Constrain urllib3 to ensure we deal with CVE-2020-26137 and CVE-2021-33503
-urllib3>=1.26.5
+# Temporary setting an upper bound, to prevent compat issues with urllib3>=2
+# https://github.com/home-assistant/core/issues/97248
+urllib3>=1.26.5,<2
 
 # Constrain httplib2 to protect against GHSA-93xj-8mrv-444m
 # https://github.com/advisories/GHSA-93xj-8mrv-444m