diff --git a/chart/templates/webserver/webserver-deployment.yaml b/chart/templates/webserver/webserver-deployment.yaml
index 385270cf18e3e..35b811551d462 100644
--- a/chart/templates/webserver/webserver-deployment.yaml
+++ b/chart/templates/webserver/webserver-deployment.yaml
@@ -149,12 +149,12 @@ spec:
               containerPort: {{ .Values.ports.airflowUI }}
           livenessProbe:
             httpGet:
-              path: {{if .Values.config.webserver.base_url }}{{- with urlParse .Values.config.webserver.base_url }}{{ .path }}{{end}}{{end}}/health
+              path: {{if .Values.config.webserver.base_url }}{{- with urlParse (tpl .Values.config.webserver.base_url .) }}{{ .path }}{{end}}{{end}}/health
               port: {{ .Values.ports.airflowUI }}
 {{- if .Values.config.webserver.base_url}}
               httpHeaders:
                 - name: Host
-                  value: {{ regexReplaceAll ":\\d+$" (urlParse .Values.config.webserver.base_url).host  "" }}
+                  value: {{ regexReplaceAll ":\\d+$" (urlParse (tpl .Values.config.webserver.base_url .)).host  "" }}
 {{- end }}
             initialDelaySeconds: {{ .Values.webserver.livenessProbe.initialDelaySeconds | default 15 }}
             timeoutSeconds: {{ .Values.webserver.livenessProbe.timeoutSeconds | default 30 }}
@@ -162,12 +162,12 @@ spec:
             periodSeconds: {{ .Values.webserver.livenessProbe.periodSeconds | default 5 }}
           readinessProbe:
             httpGet:
-              path: {{if .Values.config.webserver.base_url }}{{- with urlParse .Values.config.webserver.base_url }}{{ .path }}{{end}}{{end}}/health
+              path: {{if .Values.config.webserver.base_url }}{{- with urlParse (tpl .Values.config.webserver.base_url .) }}{{ .path }}{{end}}{{end}}/health
               port: {{ .Values.ports.airflowUI }}
 {{- if .Values.config.webserver.base_url}}
               httpHeaders:
                 - name: Host
-                  value: {{ regexReplaceAll ":\\d+$" (urlParse .Values.config.webserver.base_url).host  "" }}
+                  value: {{ regexReplaceAll ":\\d+$" (urlParse (tpl .Values.config.webserver.base_url .)).host  "" }}
 {{- end }}
             initialDelaySeconds: {{ .Values.webserver.readinessProbe.initialDelaySeconds | default 15 }}
             timeoutSeconds: {{ .Values.webserver.readinessProbe.timeoutSeconds | default 30 }}
diff --git a/chart/tests/test_webserver.py b/chart/tests/test_webserver.py
index d173ca556a23b..4a586d6438067 100644
--- a/chart/tests/test_webserver.py
+++ b/chart/tests/test_webserver.py
@@ -60,11 +60,15 @@ def test_should_add_path_to_liveness_and_readiness_probes(self):
             == "/mypath/path/health"
         )
 
-    def test_should_not_contain_host_header_if_host_empty_string(self):
-        docs = render_chart(
-            values={},
-            show_only=["templates/webserver/webserver-deployment.yaml"],
-        )
+    @parameterized.expand(
+        [
+            ({"config": {"webserver": {"base_url": ""}}},),
+            ({},),
+        ]
+    )
+    def test_should_not_contain_host_header(self, values):
+        print(values)
+        docs = render_chart(values=values, show_only=["templates/webserver/webserver-deployment.yaml"])
 
         assert (
             jmespath.search("spec.template.spec.containers[0].livenessProbe.httpGet.httpHeaders", docs[0])
@@ -75,38 +79,27 @@ def test_should_not_contain_host_header_if_host_empty_string(self):
             is None
         )
 
-    def test_should_not_contain_host_header_if_base_url_not_set(self):
+    def test_should_use_templated_base_url_for_probes(self):
         docs = render_chart(
             values={
                 "config": {
-                    "webserver": {"base_url": ""},
+                    "webserver": {
+                        "base_url": "https://{{ .Release.Name }}.com:21222/mypath/{{ .Release.Name }}/path"
+                    },
                 }
             },
             show_only=["templates/webserver/webserver-deployment.yaml"],
         )
+        container = jmespath.search("spec.template.spec.containers[0]", docs[0])
 
-        assert (
-            jmespath.search("spec.template.spec.containers[0].livenessProbe.httpGet.httpHeaders", docs[0])
-            is None
+        assert {"name": "Host", "value": "RELEASE-NAME.com"} in jmespath.search(
+            "livenessProbe.httpGet.httpHeaders", container
         )
-        assert (
-            jmespath.search("spec.template.spec.containers[0].readinessProbe.httpGet.httpHeaders", docs[0])
-            is None
-        )
-
-    def test_should_not_contain_host_header_by_default(self):
-        docs = render_chart(
-            show_only=["templates/webserver/webserver-deployment.yaml"],
-        )
-
-        assert (
-            jmespath.search("spec.template.spec.containers[0].livenessProbe.httpGet.httpHeaders", docs[0])
-            is None
-        )
-        assert (
-            jmespath.search("spec.template.spec.containers[0].readinessProbe.httpGet.httpHeaders", docs[0])
-            is None
+        assert {"name": "Host", "value": "RELEASE-NAME.com"} in jmespath.search(
+            "readinessProbe.httpGet.httpHeaders", container
         )
+        assert "/mypath/RELEASE-NAME/path/health" == jmespath.search("livenessProbe.httpGet.path", container)
+        assert "/mypath/RELEASE-NAME/path/health" == jmespath.search("readinessProbe.httpGet.path", container)
 
     def test_should_add_volume_and_volume_mount_when_exist_webserver_config(self):
         docs = render_chart(