diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index a182859b2c..024cb6abc1 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -4,6 +4,11 @@ Changelog
 in development
 --------------
 
+Fixed
+~~~~~
+
+* Fix redis SSL problems with sentinel #5660
+
 
 3.7.0 - May 05, 2022
 --------------------
diff --git a/fixed-requirements.txt b/fixed-requirements.txt
index 2fe06338c9..eb3b9adf3e 100644
--- a/fixed-requirements.txt
+++ b/fixed-requirements.txt
@@ -50,7 +50,7 @@ python-keyczar==0.716
 pytz==2021.1
 pywinrm==0.4.1
 pyyaml==5.4.1
-redis==3.5.3
+redis==4.1.4
 requests[security]==2.25.1
 retrying==1.3.3
 routes==2.4.1
diff --git a/requirements.txt b/requirements.txt
index d2186ae726..e3890d0b80 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -60,7 +60,7 @@ python-statsd==2.1.0
 pytz==2021.1
 pywinrm==0.4.1
 pyyaml==5.4.1
-redis==3.5.3
+redis==4.1.4
 rednose
 requests[security]==2.25.1
 retrying==1.3.3
diff --git a/st2common/requirements.txt b/st2common/requirements.txt
index 41d31e328c..268a88acf7 100644
--- a/st2common/requirements.txt
+++ b/st2common/requirements.txt
@@ -35,7 +35,7 @@ pymongo==3.11.3
 python-dateutil==2.8.1
 python-statsd==2.1.0
 pyyaml==5.4.1
-redis==3.5.3
+redis==4.1.4
 requests[security]==2.25.1
 retrying==1.3.3
 routes==2.4.1
diff --git a/st2common/st2common/util/monkey_patch.py b/st2common/st2common/util/monkey_patch.py
index 76b4a191de..1f0bb42cb4 100644
--- a/st2common/st2common/util/monkey_patch.py
+++ b/st2common/st2common/util/monkey_patch.py
@@ -43,7 +43,13 @@ def monkey_patch(patch_thread=None):
                          patched unless debugger is used.
     :type patch_thread: ``bool``
     """
+    # Eventlet when patched doesn't throw the standard ssl error on timeout, which can break
+    # some third-party libraries including redis SSL.
+    # See: https://github.com/eventlet/eventlet/issues/692
+    # Therefore set the patched ssl module to use the standard socket.timeout exception
+    from eventlet.green import ssl
     import eventlet
+    from socket import timeout
 
     if patch_thread is None:
         patch_thread = not is_use_debugger_flag_provided()
@@ -51,6 +57,7 @@ def monkey_patch(patch_thread=None):
     eventlet.monkey_patch(
         os=True, select=True, socket=True, thread=patch_thread, time=True
     )
+    ssl.timeout_exc = timeout
 
 
 def use_select_poll_workaround(nose_only=True):