diff --git a/charts/enterprise/vaultwarden/Chart.yaml b/charts/enterprise/vaultwarden/Chart.yaml
index fcd8189c53e..e0e464e4ff9 100644
--- a/charts/enterprise/vaultwarden/Chart.yaml
+++ b/charts/enterprise/vaultwarden/Chart.yaml
@@ -25,7 +25,7 @@ sources:
   - https://github.com/truecharts/charts/tree/master/charts/enterprise/vaultwarden
   - https://github.com/dani-garcia/vaultwarden
 type: application
-version: 22.0.0
+version: 23.0.0
 annotations:
   truecharts.org/catagories: |
     - security
diff --git a/charts/enterprise/vaultwarden/questions.yaml b/charts/enterprise/vaultwarden/questions.yaml
index 26a0b50ccb7..8f7d4c7a49a 100644
--- a/charts/enterprise/vaultwarden/questions.yaml
+++ b/charts/enterprise/vaultwarden/questions.yaml
@@ -200,14 +200,21 @@ questions:
                       schema:
                         type: string
                         default: ""
-                    - variable: ssl
+                    - variable: security
                       label: "Enable SSL connection"
                       schema:
-                        type: boolean
-                        default: true
+                        type: string
+                        default: "starttls"
+                        enum:
+                          - value: "starttls"
+                            description: "STARTTLS (587)"
+                          - value: "force_tls"
+                            description: "FORCE_TLS (465)"
+                          - value: "off"
+                            description: "OFF (25)"
                     - variable: port
                       label: "SMTP port"
-                      description: "Usually: 25 without SSL, 587 with SSL"
+                      description: "Usually: 587 with STARTTLS, 465 with FORCE_TLS, and 25 without SSL"
                       schema:
                         type: int
                         default: 587
diff --git a/charts/enterprise/vaultwarden/templates/_configmap.tpl b/charts/enterprise/vaultwarden/templates/_configmap.tpl
index a396837e5a4..7cc26147b0e 100644
--- a/charts/enterprise/vaultwarden/templates/_configmap.tpl
+++ b/charts/enterprise/vaultwarden/templates/_configmap.tpl
@@ -47,7 +47,7 @@ data:
   SMTP_FROM_NAME: {{ .Values.vaultwarden.smtp.fromName | quote }}
   {{- end }}
   {{- if .Values.vaultwarden.smtp.ssl }}
-  SMTP_SSL: {{ .Values.vaultwarden.smtp.ssl | quote }}
+  SMTP_SECURITY: {{ .Values.vaultwarden.smtp.security | quote }}
   {{- end }}
   {{- if .Values.vaultwarden.smtp.port }}
   SMTP_PORT: {{ .Values.vaultwarden.smtp.port | quote }}
diff --git a/charts/enterprise/vaultwarden/values.yaml b/charts/enterprise/vaultwarden/values.yaml
index c6562326fd0..2cbd440e0e1 100644
--- a/charts/enterprise/vaultwarden/values.yaml
+++ b/charts/enterprise/vaultwarden/values.yaml
@@ -95,8 +95,8 @@ vaultwarden:
     ## SMTP sender name, defaults to 'Bitwarden_RS'.
     # fromName: ""
     ## Enable SSL connection.
-    # ssl: true
-    ## SMTP port. Defaults to 25 without SSL, 587 with SSL.
+    # security: starttls
+    ## SMTP port. Defaults to 587 with STARTTLS, 465 with FORCE_TLS, and 25 without SSL.
     # port: 587
     ## SMTP Authentication Mechanisms. Comma-separated options: 'Plain', 'Login' and 'Xoauth2'. Defaults to 'Plain'.
     # authMechanism: Plain