diff --git a/charts/armada/templates/deployment-api.yaml b/charts/armada/templates/deployment-api.yaml
index 534cdf48..9d3bff45 100644
--- a/charts/armada/templates/deployment-api.yaml
+++ b/charts/armada/templates/deployment-api.yaml
@@ -153,6 +153,16 @@ spec:
 {{- if .Values.conf.tiller.trace }}
             - -trace
 {{- end }}
+          lifecycle:
+            preStop:
+              exec:
+                command:
+                  # Delay tiller termination so that it has a chance to finish
+                  # deploying releases including marking them with
+                  # DEPLOYED/FAILED status, otherwise they can get stuck in
+                  # PENDING_*** status.
+                  - sleep
+                  - "{{ .Values.conf.tiller.prestop_sleep }}"
           ports:
             - name: tiller
               containerPort: {{ .Values.conf.tiller.port }}
diff --git a/charts/armada/values.yaml b/charts/armada/values.yaml
index 115034ba..d18bd254 100644
--- a/charts/armada/values.yaml
+++ b/charts/armada/values.yaml
@@ -209,6 +209,9 @@ conf:
     namespace: kube-system
     # Limit the maximum number of revisions saved per release. 0 for no limit.
     history_max: 0
+    # Note: Defaulting to the (default) kubernetes grace period, as anything
+    # greater than that will have no effect.
+    prestop_sleep: 30
 
 pod:
   security_context:
diff --git a/charts/tiller/templates/deployment-tiller.yaml b/charts/tiller/templates/deployment-tiller.yaml
index a7711891..2607f9a0 100644
--- a/charts/tiller/templates/deployment-tiller.yaml
+++ b/charts/tiller/templates/deployment-tiller.yaml
@@ -77,6 +77,16 @@ spec:
 {{- if .Values.conf.tiller.trace }}
             - -trace
 {{- end }}
+          lifecycle:
+            preStop:
+              exec:
+                command:
+                  # Delay tiller termination so that it has a chance to finish
+                  # deploying releases including marking them with
+                  # DEPLOYED/FAILED status, otherwise they can get stuck in
+                  # PENDING_*** status.
+                  - sleep
+                  - "{{ .Values.conf.tiller.prestop_sleep }}"
           ports:
             - name: tiller
               containerPort: 44134
diff --git a/charts/tiller/values.yaml b/charts/tiller/values.yaml
index e9ab128d..59170ae8 100644
--- a/charts/tiller/values.yaml
+++ b/charts/tiller/values.yaml
@@ -41,6 +41,9 @@ conf:
   tiller:
     verbosity: 5
     trace: false
+    # Note: Defaulting to the (default) kubernetes grace period, as anything
+    # greater than that will have no effect.
+    prestop_sleep: 30
 
 pod:
   resources: