diff --git a/templates/server-ingress.yaml b/templates/server-ingress.yaml
index 7c19f5fea..5faac60f4 100644
--- a/templates/server-ingress.yaml
+++ b/templates/server-ingress.yaml
@@ -2,6 +2,7 @@
 {{ template "vault.mode" . }}
 {{- if ne .mode "external" }}
 {{- if .Values.server.ingress.enabled -}}
+{{- $extraPaths := .Values.server.ingress.extraPaths -}}
 {{- $serviceName := include "vault.fullname" . -}}
 {{- if and (eq .mode "ha" ) (and (eq (.Values.server.service.enabled | toString) "true" ) (eq (.Values.global.enabled | toString) "true")) }}
 {{- $serviceName = printf "%s-%s" $serviceName "active" -}}
@@ -41,6 +42,9 @@ spec:
     - host: {{ .host | quote }}
       http:
         paths:
+{{ if $extraPaths }}
+{{ toYaml $extraPaths | indent 10 }}
+{{- end }}
         {{- range (.paths | default (list "/")) }}
           - path: {{ . }}
             backend:
diff --git a/test/unit/server-ingress.bats b/test/unit/server-ingress.bats
index 5af493847..bf191c3a2 100755
--- a/test/unit/server-ingress.bats
+++ b/test/unit/server-ingress.bats
@@ -57,6 +57,43 @@ load _helpers
 
 }
 
+@test "server/ingress: extra paths prepend host configuration" {
+  cd `chart_dir`
+
+  local actual=$(helm template \
+      --show-only templates/server-ingress.yaml \
+      --set 'server.ingress.enabled=true' \
+      --set 'server.ingress.hosts[0].host=test.com' \
+      --set 'server.ingress.hosts[0].paths[0]=/' \
+      --set 'server.ingress.extraPaths[0].path=/annotation-service' \
+      --set 'server.ingress.extraPaths[0].backend.serviceName=ssl-redirect' \
+      . | tee /dev/stderr |
+      yq  -r '.spec.rules[0].http.paths[0].backend.serviceName' | tee /dev/stderr)
+  [ "${actual}" = 'ssl-redirect' ]
+
+  local actual=$(helm template \
+      --show-only templates/server-ingress.yaml \
+      --set 'server.ingress.enabled=true' \
+      --set 'server.ingress.hosts[0].host=test.com' \
+      --set 'server.ingress.hosts[0].paths[0]=/' \
+      --set 'server.ingress.extraPaths[0].path=/annotation-service' \
+      --set 'server.ingress.extraPaths[0].backend.serviceName=ssl-redirect' \
+      . | tee /dev/stderr |
+      yq  -r '.spec.rules[0].http.paths[0].path' | tee /dev/stderr)
+  [ "${actual}" = '/annotation-service' ]
+
+  local actual=$(helm template \
+      --show-only templates/server-ingress.yaml \
+      --set 'server.ingress.enabled=true' \
+      --set 'server.ingress.hosts[0].host=test.com' \
+      --set 'server.ingress.hosts[0].paths[0]=/' \
+      --set 'server.ingress.extraPaths[0].path=/annotation-service' \
+      --set 'server.ingress.extraPaths[0].backend.serviceName=ssl-redirect' \
+      . | tee /dev/stderr |
+      yq  -r '.spec.rules[0].http.paths[1].path' | tee /dev/stderr)
+  [ "${actual}" = '/' ]
+}
+
 @test "server/ingress: labels gets added to object" {
   cd `chart_dir`
 
diff --git a/values.yaml b/values.yaml
index 2aa0e3bbc..ac71ebeda 100644
--- a/values.yaml
+++ b/values.yaml
@@ -206,7 +206,12 @@ server:
     hosts:
       - host: chart-example.local
         paths: []
-
+    ## Extra paths to prepend to the host configuration. This is useful when working with annotation based services.
+    extraPaths: []
+    # - path: /*
+    #   backend:
+    #     serviceName: ssl-redirect
+    #     servicePort: use-annotation
     tls: []
     #  - secretName: chart-example-tls
     #    hosts: