diff --git a/CHANGELOG.md b/CHANGELOG.md
index af4eef796f41..335ea17e5654 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,8 @@ IMPROVEMENTS:
 * Updated the default Consul image to `hashicorp/consul:1.9.0`.
 * Updated the default consul-k8s image to `hashicorp/consul-k8s:0.21.0`.
 * Updated the default envoy image to `envoyproxy/envoy-alpine:v1.16.0`.
+* Add Server ConfigMap and Client ConfigMap values as hashes on Server StatefulSet and Client DaemonSet annotations respectively. This recreates
+  the Server/Client Pod when the Server/Client ConfigMap is updated via `helm upgrade`. This updates the previously hashed values of the extraConfig. [[GH-550](https://github.com/hashicorp/consul-helm/pull/550)]
 
 ## 0.26.0 (Nov 12, 2020)
 
diff --git a/templates/client-daemonset.yaml b/templates/client-daemonset.yaml
index 9c5fa9fcb1c9..fda6fa9d9d9b 100644
--- a/templates/client-daemonset.yaml
+++ b/templates/client-daemonset.yaml
@@ -32,7 +32,7 @@ spec:
         hasDNS: "true"
       annotations:
         "consul.hashicorp.com/connect-inject": "false"
-        "consul.hashicorp.com/config-checksum": {{ .Values.client.extraConfig | sha256sum }}
+        "consul.hashicorp.com/config-checksum": {{ include (print $.Template.BasePath "/client-config-configmap.yaml") . | sha256sum }}
         {{- if .Values.client.annotations }}
           {{- tpl .Values.client.annotations . | nindent 8 }}
         {{- end }}
diff --git a/templates/server-statefulset.yaml b/templates/server-statefulset.yaml
index 7ff5f22353b4..d9b518dca8a9 100644
--- a/templates/server-statefulset.yaml
+++ b/templates/server-statefulset.yaml
@@ -44,7 +44,7 @@ spec:
         {{- end }}
       annotations:
         "consul.hashicorp.com/connect-inject": "false"
-        "consul.hashicorp.com/config-checksum": {{ .Values.server.extraConfig | sha256sum }}
+        "consul.hashicorp.com/config-checksum": {{ include (print $.Template.BasePath "/server-config-configmap.yaml") . | sha256sum }}
         {{- if .Values.server.annotations }}
           {{- tpl .Values.server.annotations . | nindent 8 }}
         {{- end }}
diff --git a/test/unit/client-daemonset.bats b/test/unit/client-daemonset.bats
index 706fa60f2382..06bf9ce02a50 100755
--- a/test/unit/client-daemonset.bats
+++ b/test/unit/client-daemonset.bats
@@ -370,7 +370,7 @@ load _helpers
 }
 
 #--------------------------------------------------------------------
-# extraConfig
+# config-configmap
 
 @test "client/DaemonSet: adds config-checksum annotation when extraConfig is blank" {
   cd `chart_dir`
@@ -378,7 +378,11 @@ load _helpers
       -s templates/client-daemonset.yaml  \
       . | tee /dev/stderr |
       yq -r '.spec.template.metadata.annotations."consul.hashicorp.com/config-checksum"' | tee /dev/stderr)
-  [ "${actual}" = ca3d163bab055381827226140568f3bef7eaac187cebd76878e0b63e9e442356 ]
+  if [[ $(v2) ]]; then
+    [ "${actual}" = c8c40738a067bbeb4392ec038ad3b1a94d3cd747118b62d72825e44246814951 ]
+  else
+    [ "${actual}" = 1cfdb3a2989f349021d0a4beb7d854a1de35b89d45184caf5290c49460955a33 ]
+  fi
 }
 
 @test "client/DaemonSet: adds config-checksum annotation when extraConfig is provided" {
@@ -388,7 +392,25 @@ load _helpers
       --set 'client.extraConfig="{\"hello\": \"world\"}"' \
       . | tee /dev/stderr |
       yq -r '.spec.template.metadata.annotations."consul.hashicorp.com/config-checksum"' | tee /dev/stderr)
-  [ "${actual}" = 83df36fdaf1b4acb815f1764f9ff2782c520ca012511f282ba9c57a04401a239 ]
+  if [[ $(v2) ]]; then
+    [ "${actual}" = 7e0bc6cb882996b13c2aad2295ea0a3573185456ba8e1770519b86779075da47 ]
+  else
+    [ "${actual}" = d864eda42c5c072921663de14fd9e0593a9ebce192da82a3239e6ded98ff2e8d ]
+  fi
+}
+
+@test "client/DaemonSet: adds config-checksum annotation when client config is updated" {
+  cd `chart_dir`
+  local actual=$(helm template \
+      -s templates/client-daemonset.yaml  \
+      --set 'connectInject.enabled=true' \
+      . | tee /dev/stderr |
+      yq -r '.spec.template.metadata.annotations."consul.hashicorp.com/config-checksum"' | tee /dev/stderr)
+  if [[ $(v2) ]]; then
+    [ "${actual}" = ab9a9f78fc78a0c7509ec21d2f270052c556c28a1eceb26e4b40ef0068a34889 ]
+  else
+    [ "${actual}" = 56e95d32e8bc31f566498a05dc8e1e08b2cb049880ce589d2e9143f45308638c ]
+  fi
 }
 
 #--------------------------------------------------------------------
diff --git a/test/unit/server-statefulset.bats b/test/unit/server-statefulset.bats
index bebe27af487a..4f9321f35a5e 100755
--- a/test/unit/server-statefulset.bats
+++ b/test/unit/server-statefulset.bats
@@ -402,7 +402,7 @@ load _helpers
   [ "${actual}" = "bar" ]
 }
 #--------------------------------------------------------------------
-# extraConfig
+# config-configmap
 
 @test "server/StatefulSet: adds config-checksum annotation when extraConfig is blank" {
   cd `chart_dir`
@@ -410,7 +410,11 @@ load _helpers
       -s templates/server-statefulset.yaml  \
       . | tee /dev/stderr |
       yq -r '.spec.template.metadata.annotations."consul.hashicorp.com/config-checksum"' | tee /dev/stderr)
-  [ "${actual}" = ca3d163bab055381827226140568f3bef7eaac187cebd76878e0b63e9e442356 ]
+  if [[ $(v2) ]]; then
+    [ "${actual}" = 5d152ec45fdfa5a4cb95eee6aae027212a5adad08c6904e4089545afea0ab8f3 ]
+  else
+    [ "${actual}" = 355e9f414430ab2464a6948fcd763b4c79b7ad04b382820e77fb977021bbb635 ]
+  fi
 }
 
 @test "server/StatefulSet: adds config-checksum annotation when extraConfig is provided" {
@@ -420,7 +424,25 @@ load _helpers
       --set 'server.extraConfig="{\"hello\": \"world\"}"' \
       . | tee /dev/stderr |
       yq -r '.spec.template.metadata.annotations."consul.hashicorp.com/config-checksum"' | tee /dev/stderr)
-  [ "${actual}" = 83df36fdaf1b4acb815f1764f9ff2782c520ca012511f282ba9c57a04401a239 ]
+  if [[ $(v2) ]]; then
+    [ "${actual}" = 67ea7116413d1780d84055440a077abffcf5e520c997ddaf002f446bdcf19f0f ]
+  else
+    [ "${actual}" = d6874107a1da35a40f68469b1c8f58e0a8360af511ab931ed84b312dbbc11f45 ]
+  fi
+}
+
+@test "server/StatefulSet: adds config-checksum annotation when config is updated" {
+  cd `chart_dir`
+  local actual=$(helm template \
+      -s templates/server-statefulset.yaml  \
+      --set 'global.acls.manageSystemACLs=true' \
+      . | tee /dev/stderr |
+      yq -r '.spec.template.metadata.annotations."consul.hashicorp.com/config-checksum"' | tee /dev/stderr)
+  if [[ $(v2) ]]; then
+    [ "${actual}" = 6519afe07b3c4d5697b92cba372f2aca9852cd4f1899216cd5cf620f46e9c178 ]
+  else
+    [ "${actual}" = 8bd7707a967de94e300c8df78fd0de469c3e0c40d816105f3230c5715febd1c7 ]
+  fi
 }
 
 #--------------------------------------------------------------------