diff --git a/requirements-dev.txt b/requirements-dev.txt
index 58e89de4a..d5c48bede 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -145,7 +145,7 @@ configobj==5.0.9
     #   certbot
 coverage==7.14.1
     # via -r requirements-tests.txt
-cryptography==46.0.7
+cryptography==49.0.0
     # via
     #   -r requirements-tests.txt
     #   acme
@@ -611,7 +611,7 @@ pynacl==1.6.2
     # via
     #   -r requirements-tests.txt
     #   paramiko
-pyopenssl==26.2.0
+pyopenssl==26.3.0
     # via
     #   -r requirements-tests.txt
     #   acme
diff --git a/requirements-docs.txt b/requirements-docs.txt
index 4f16a2658..e365577f6 100644
--- a/requirements-docs.txt
+++ b/requirements-docs.txt
@@ -158,7 +158,7 @@ configobj==5.0.9
     #   certbot
 coverage==7.14.1
     # via -r requirements-tests.txt
-cryptography==46.0.7
+cryptography==49.0.0
     # via
     #   -r requirements-docs.in
     #   -r requirements-tests.txt
@@ -622,7 +622,7 @@ pynacl==1.6.2
     # via
     #   -r requirements-tests.txt
     #   paramiko
-pyopenssl==26.2.0
+pyopenssl==26.3.0
     # via
     #   -r requirements-docs.in
     #   -r requirements-tests.txt
diff --git a/requirements-tests.txt b/requirements-tests.txt
index 77b469a6c..9b49aeb84 100644
--- a/requirements-tests.txt
+++ b/requirements-tests.txt
@@ -133,7 +133,7 @@ configobj==5.0.9
     #   certbot
 coverage==7.14.1
     # via -r requirements-tests.in
-cryptography==46.0.7
+cryptography==49.0.0
     # via
     #   -r requirements.txt
     #   acme
@@ -495,7 +495,7 @@ pynacl==1.6.2
     # via
     #   -r requirements.txt
     #   paramiko
-pyopenssl==26.2.0
+pyopenssl==26.3.0
     # via
     #   -r requirements.txt
     #   acme
diff --git a/requirements.txt b/requirements.txt
index 993a8d534..e8c3795ff 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -78,7 +78,7 @@ configargparse==1.7.5
     # via certbot
 configobj==5.0.9
     # via certbot
-cryptography==46.0.7
+cryptography==49.0.0
     # via
     #   -r requirements.in
     #   acme
@@ -275,7 +275,7 @@ pyjwt==2.12.1
     # via -r requirements.in
 pynacl==1.6.2
     # via paramiko
-pyopenssl==26.2.0
+pyopenssl==26.3.0
     # via
     #   -r requirements.in
     #   acme