diff --git a/homeassistant/package_constraints.txt b/homeassistant/package_constraints.txt
index bf84644f02e..3759f57361b 100644
--- a/homeassistant/package_constraints.txt
+++ b/homeassistant/package_constraints.txt
@@ -17,7 +17,7 @@ bluetooth-auto-recovery==1.0.3
 bluetooth-data-tools==0.3.1
 certifi>=2021.5.30
 ciso8601==2.3.0
-cryptography==38.0.3
+cryptography==39.0.0
 dbus-fast==1.84.0
 fnvhash==0.1.0
 hass-nabucasa==0.61.0
@@ -33,6 +33,7 @@ paho-mqtt==1.6.1
 pillow==9.4.0
 pip>=21.0,<22.4
 psutil-home-assistant==0.0.1
+pyOpenSSL==23.0.0
 pyserial==3.5
 python-slugify==4.0.1
 pyudev==0.23.2
@@ -138,3 +139,7 @@ uamqp==1.6.0
 # Matplotlib 3.6.2 has issues building wheels on armhf/armv7
 # We need at least >=2.1.0 (tensorflow integration -> pycocotools)
 matplotlib==3.6.1
+
+# pyOpenSSL 23.0.0 or later required to avoid import errors when
+# cryptography 39.0.0 is installed with botocore
+pyOpenSSL>=23.0.0
diff --git a/pyproject.toml b/pyproject.toml
index bd1f82fe787..6c69069c873 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -42,7 +42,9 @@ dependencies    = [
     "lru-dict==1.1.8",
     "PyJWT==2.5.0",
     # PyJWT has loose dependency. We want the latest one.
-    "cryptography==38.0.3",
+    "cryptography==39.0.0",
+    # pyOpenSSL 23.0.0 is required to work with cryptography 39+
+    "pyOpenSSL==23.0.0",
     "orjson==3.8.4",
     "pip>=21.0,<22.4",
     "python-slugify==4.0.1",
diff --git a/requirements.txt b/requirements.txt
index bc3da8ff965..4b3feec9a0b 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -16,7 +16,8 @@ ifaddr==0.1.7
 jinja2==3.1.2
 lru-dict==1.1.8
 PyJWT==2.5.0
-cryptography==38.0.3
+cryptography==39.0.0
+pyOpenSSL==23.0.0
 orjson==3.8.4
 pip>=21.0,<22.4
 python-slugify==4.0.1
diff --git a/script/gen_requirements_all.py b/script/gen_requirements_all.py
index 6f4e017a56e..4456a3312b5 100755
--- a/script/gen_requirements_all.py
+++ b/script/gen_requirements_all.py
@@ -149,6 +149,10 @@ uamqp==1.6.0
 # Matplotlib 3.6.2 has issues building wheels on armhf/armv7
 # We need at least >=2.1.0 (tensorflow integration -> pycocotools)
 matplotlib==3.6.1
+
+# pyOpenSSL 23.0.0 or later required to avoid import errors when
+# cryptography 39.0.0 is installed with botocore
+pyOpenSSL>=23.0.0
 """
 
 IGNORE_PRE_COMMIT_HOOK_ID = (