diff --git a/test/tools/router_check/router.cc b/test/tools/router_check/router.cc
index 5eeadc7a1bb1..fbd9eaed7031 100644
--- a/test/tools/router_check/router.cc
+++ b/test/tools/router_check/router.cc
@@ -224,13 +224,13 @@ bool RouterCheckTool::compareCluster(ToolConfig& tool_config, const std::string&
 
 bool RouterCheckTool::compareCluster(
     ToolConfig& tool_config, const envoy::RouterCheckToolSchema::ValidationAssert& expected) {
-  if (expected.cluster_name().empty()) {
+  if (!expected.has_cluster_name()) {
     return true;
   }
   if (tool_config.route_ == nullptr) {
-    return compareResults("", expected.cluster_name(), "cluster_name");
+    return compareResults("", expected.cluster_name().value(), "cluster_name");
   }
-  return compareCluster(tool_config, expected.cluster_name());
+  return compareCluster(tool_config, expected.cluster_name().value());
 }
 
 bool RouterCheckTool::compareVirtualCluster(ToolConfig& tool_config, const std::string& expected) {
@@ -251,13 +251,13 @@ bool RouterCheckTool::compareVirtualCluster(ToolConfig& tool_config, const std::
 
 bool RouterCheckTool::compareVirtualCluster(
     ToolConfig& tool_config, const envoy::RouterCheckToolSchema::ValidationAssert& expected) {
-  if (expected.virtual_cluster_name().empty()) {
+  if (!expected.has_virtual_cluster_name()) {
     return true;
   }
   if (tool_config.route_ == nullptr) {
-    return compareResults("", expected.virtual_cluster_name(), "virtual_cluster_name");
+    return compareResults("", expected.virtual_cluster_name().value(), "virtual_cluster_name");
   }
-  return compareVirtualCluster(tool_config, expected.virtual_cluster_name());
+  return compareVirtualCluster(tool_config, expected.virtual_cluster_name().value());
 }
 
 bool RouterCheckTool::compareVirtualHost(ToolConfig& tool_config, const std::string& expected) {
@@ -275,13 +275,13 @@ bool RouterCheckTool::compareVirtualHost(ToolConfig& tool_config, const std::str
 
 bool RouterCheckTool::compareVirtualHost(
     ToolConfig& tool_config, const envoy::RouterCheckToolSchema::ValidationAssert& expected) {
-  if (expected.virtual_host_name().empty()) {
+  if (!expected.has_virtual_host_name()) {
     return true;
   }
   if (tool_config.route_ == nullptr) {
-    return compareResults("", expected.virtual_host_name(), "virtual_host_name");
+    return compareResults("", expected.virtual_host_name().value(), "virtual_host_name");
   }
-  return compareVirtualHost(tool_config, expected.virtual_host_name());
+  return compareVirtualHost(tool_config, expected.virtual_host_name().value());
 }
 
 bool RouterCheckTool::compareRewritePath(ToolConfig& tool_config, const std::string& expected) {
@@ -306,13 +306,13 @@ bool RouterCheckTool::compareRewritePath(ToolConfig& tool_config, const std::str
 
 bool RouterCheckTool::compareRewritePath(
     ToolConfig& tool_config, const envoy::RouterCheckToolSchema::ValidationAssert& expected) {
-  if (expected.path_rewrite().empty()) {
+  if (!expected.has_path_rewrite()) {
     return true;
   }
   if (tool_config.route_ == nullptr) {
-    return compareResults("", expected.path_rewrite(), "path_rewrite");
+    return compareResults("", expected.path_rewrite().value(), "path_rewrite");
   }
-  return compareRewritePath(tool_config, expected.path_rewrite());
+  return compareRewritePath(tool_config, expected.path_rewrite().value());
 }
 
 bool RouterCheckTool::compareRewriteHost(ToolConfig& tool_config, const std::string& expected) {
@@ -337,13 +337,13 @@ bool RouterCheckTool::compareRewriteHost(ToolConfig& tool_config, const std::str
 
 bool RouterCheckTool::compareRewriteHost(
     ToolConfig& tool_config, const envoy::RouterCheckToolSchema::ValidationAssert& expected) {
-  if (expected.host_rewrite().empty()) {
+  if (!expected.has_host_rewrite()) {
     return true;
   }
   if (tool_config.route_ == nullptr) {
-    return compareResults("", expected.host_rewrite(), "host_rewrite");
+    return compareResults("", expected.host_rewrite().value(), "host_rewrite");
   }
-  return compareRewriteHost(tool_config, expected.host_rewrite());
+  return compareRewriteHost(tool_config, expected.host_rewrite().value());
 }
 
 bool RouterCheckTool::compareRedirectPath(ToolConfig& tool_config, const std::string& expected) {
@@ -361,13 +361,13 @@ bool RouterCheckTool::compareRedirectPath(ToolConfig& tool_config, const std::st
 
 bool RouterCheckTool::compareRedirectPath(
     ToolConfig& tool_config, const envoy::RouterCheckToolSchema::ValidationAssert& expected) {
-  if (expected.path_redirect().empty()) {
+  if (!expected.has_path_redirect()) {
     return true;
   }
   if (tool_config.route_ == nullptr) {
-    return compareResults("", expected.path_redirect(), "path_redirect");
+    return compareResults("", expected.path_redirect().value(), "path_redirect");
   }
-  return compareRedirectPath(tool_config, expected.path_redirect());
+  return compareRedirectPath(tool_config, expected.path_redirect().value());
 }
 
 bool RouterCheckTool::compareHeaderField(
diff --git a/test/tools/router_check/test/config/ComprehensiveRoutes.golden.proto.json b/test/tools/router_check/test/config/ComprehensiveRoutes.golden.proto.json
new file mode 100644
index 000000000000..ebc21381c347
--- /dev/null
+++ b/test/tools/router_check/test/config/ComprehensiveRoutes.golden.proto.json
@@ -0,0 +1,63 @@
+{
+  "tests": [
+    {
+      "test_name": "Test 1",
+      "input": {
+        "authority": "www.lyft.com",
+        "path": "/new_endpoint",
+        "method": "GET"
+      },
+      "validate": {
+        "cluster_name": "www2",
+        "virtual_cluster_name": "other",
+        "virtual_host_name": "www2_host",
+        "path_rewrite": "/api/new_endpoint",
+        "host_rewrite": "www.lyft.com",
+        "path_redirect": ""
+      }
+    },
+    {
+      "test_name": "Test 2",
+      "input": {
+        "authority": "www.lyft.com",
+        "path": "/",
+        "method": "GET"
+      },
+      "validate": {
+        "cluster_name": "root_www2",
+        "virtual_cluster_name": "other",
+        "virtual_host_name": "www2_host",
+        "path_rewrite": "/",
+        "host_rewrite": "www.lyft.com",
+        "path_redirect": ""
+      }
+    },
+    {
+      "test_name": "Test 3",
+      "input": {
+        "authority": "www.lyft.com",
+        "path": "/foobar",
+        "method": "GET"
+      },
+      "validate": {
+        "cluster_name": "www2",
+        "virtual_cluster_name": "other",
+        "virtual_host_name": "www2_host",
+        "path_rewrite": "/foobar",
+        "host_rewrite": "www.lyft.com",
+        "path_redirect": ""
+      }
+    },
+    {
+      "test_name": "Test 4",
+      "input": {
+        "authority": "www.lyft.com",
+        "path": "/users/123",
+        "method": "PUT"
+      },
+      "validate": {
+        "virtual_cluster_name": "update_user"
+      }
+    }
+  ]
+}
diff --git a/test/tools/router_check/test/config/ComprehensiveRoutes.yaml b/test/tools/router_check/test/config/ComprehensiveRoutes.yaml
index 0613410256ca..6efad99a099e 100644
--- a/test/tools/router_check/test/config/ComprehensiveRoutes.yaml
+++ b/test/tools/router_check/test/config/ComprehensiveRoutes.yaml
@@ -17,6 +17,11 @@ virtual_hosts:
         route:
           cluster: www2
     virtual_clusters:
-      - pattern: ^/users/\d+$
-        method: PUT
+      - headers:
+        - name: :path
+          safe_regex_match:
+            google_re2: {}
+            regex: ^/users/\d+$
+        - name: :method
+          exact_match: PUT
         name: update_user
diff --git a/test/tools/router_check/test/config/Weighted.golden.proto.pb_text b/test/tools/router_check/test/config/Weighted.golden.proto.pb_text
index c2ab5d18c377..fa7dedcb27c5 100644
--- a/test/tools/router_check/test/config/Weighted.golden.proto.pb_text
+++ b/test/tools/router_check/test/config/Weighted.golden.proto.pb_text
@@ -8,7 +8,7 @@ tests {
     method: "GET"
   }
   validate: {
-    path_redirect: ""
+    path_redirect: { value: "" }
   }
 }
 
@@ -21,6 +21,6 @@ tests {
     random_value: 115
   }
   validate: {
-    cluster_name: "cluster1"
+    cluster_name: { value: "cluster1" }
   }
 }
\ No newline at end of file
diff --git a/test/tools/router_check/test/route_tests.sh b/test/tools/router_check/test/route_tests.sh
index 0b06cb7425bf..1e85bea3f598 100755
--- a/test/tools/router_check/test/route_tests.sh
+++ b/test/tools/router_check/test/route_tests.sh
@@ -24,6 +24,12 @@ if [[ "${COVERAGE_OUTPUT}" != *"Current route coverage: "* ]] ; then
   exit 1
 fi
 
+COMP_COVERAGE_CMD="${PATH_BIN} -c ${PATH_CONFIG}/ComprehensiveRoutes.yaml -t ${PATH_CONFIG}/ComprehensiveRoutes.golden.proto.json --details --useproto -f "
+COVERAGE_OUTPUT=$($COMP_COVERAGE_CMD "100" "--covall" 2>&1) || echo "${COVERAGE_OUTPUT:-no-output}"
+if [[ "${COVERAGE_OUTPUT}" != *"Current route coverage: 100%"* ]] ; then
+  exit 1
+fi
+
 COMP_COVERAGE_CMD="${PATH_BIN} ${PATH_CONFIG}/ComprehensiveRoutes.yaml ${PATH_CONFIG}/ComprehensiveRoutes.golden.json --details -f "
 COVERAGE_OUTPUT=$($COMP_COVERAGE_CMD "100" "--covall" 2>&1) || echo "${COVERAGE_OUTPUT:-no-output}"
 if [[ "${COVERAGE_OUTPUT}" != *"Current route coverage: 100%"* ]] ; then
diff --git a/test/tools/router_check/validation.proto b/test/tools/router_check/validation.proto
index 9c86153cd3e9..4ff3ab35f434 100644
--- a/test/tools/router_check/validation.proto
+++ b/test/tools/router_check/validation.proto
@@ -3,6 +3,7 @@ syntax = "proto3";
 package envoy.RouterCheckToolSchema;
 
 import "envoy/api/v2/core/base.proto";
+import "google/protobuf/wrappers.proto";
 import "validate/validate.proto";
 
 // [#protodoc-title: RouterCheckTool Validation]
@@ -78,22 +79,22 @@ message ValidationInput {
 // For example, to test that no cluster match is expected use {“cluster_name”: “”}.
 message ValidationAssert {
   // Match the cluster name.
-  string cluster_name = 1;
+  google.protobuf.StringValue cluster_name = 1;
 
   // Match the virtual cluster name.
-  string virtual_cluster_name = 2;
+  google.protobuf.StringValue virtual_cluster_name = 2;
 
   // Match the virtual host name.
-  string virtual_host_name = 3;
+  google.protobuf.StringValue virtual_host_name = 3;
 
   // Match the host header field after rewrite.
-  string host_rewrite = 4;
+  google.protobuf.StringValue host_rewrite = 4;
 
   // Match the path header field after rewrite.
-  string path_rewrite = 5;
+  google.protobuf.StringValue path_rewrite = 5;
 
   // Match the returned redirect path.
-  string path_redirect = 6;
+  google.protobuf.StringValue path_redirect = 6;
 
   // Match the listed header fields.
   // Examples header fields include the “:path”, “cookie”, and “date” fields.