diff --git a/samples/dockercompose/ingress.yml b/samples/dockercompose/ingress.yml
index 704b8831..d607c5be 100644
--- a/samples/dockercompose/ingress.yml
+++ b/samples/dockercompose/ingress.yml
@@ -1,4 +1,4 @@
-apiVersion: extensions/v1beta1
+apiVersion: networking.k8s.io/v1
 kind: Ingress
 metadata:
   name: ingress-basic
diff --git a/src/Microsoft.Tye.Core/DeployApplicationKubernetesManifestStep.cs b/src/Microsoft.Tye.Core/DeployApplicationKubernetesManifestStep.cs
index a2a7ec9a..68f2259e 100644
--- a/src/Microsoft.Tye.Core/DeployApplicationKubernetesManifestStep.cs
+++ b/src/Microsoft.Tye.Core/DeployApplicationKubernetesManifestStep.cs
@@ -2,6 +2,7 @@
 // The .NET Foundation licenses this file to you under the MIT license.
 // See the LICENSE file in the project root for more information.
 
+using System;
 using System.CommandLine.Invocation;
 using System.IO;
 using System.Text;
@@ -15,7 +16,7 @@ namespace Microsoft.Tye
 
         public override async Task ExecuteAsync(OutputContext output, ApplicationBuilder application)
         {
-            using var step = output.BeginStep("");
+            using var step = output.BeginStep("Applying Kubernetes Manifests...");
 
             if (!await KubectlDetector.IsKubectlInstalledAsync(output))
             {
@@ -59,6 +60,47 @@ namespace Microsoft.Tye
             }
 
             output.WriteInfoLine($"Deployed application '{application.Name}'.");
+            if (application.Ingress.Count > 0)
+            {
+                output.WriteInfoLine($"Waiting for ingress to be deployed. This may take a long time.");
+                foreach (var ingress in application.Ingress)
+                {
+                    using var ingressStep = output.BeginStep($"Retrieving details for {ingress.Name}...");
+
+                    var done = false;
+
+                    Action<string> complete = line =>
+                    {
+                        done = line != "''";
+                        if (done)
+                        {
+                            output.WriteInfoLine($"IngressIP: {line}");
+                        }
+                    };
+
+                    var retries = 0;
+                    while (!done && retries < 60)
+                    {
+                        var ingressExitCode = await Process.ExecuteAsync(
+                            "kubectl",
+                            $"get ingress {ingress.Name} -o jsonpath='{{..ip}}'",
+                            Environment.CurrentDirectory,
+                            complete,
+                            capture.StdErr);
+
+                        if (ingressExitCode != 0)
+                        {
+                            throw new CommandException("'kubectl get ingress' failed");
+                        }
+
+                        if (!done)
+                        {
+                            await Task.Delay(2000);
+                            retries++;
+                        }
+                    }
+                }
+            }
         }
     }
 }
diff --git a/src/Microsoft.Tye.Core/KubernetesManifestGenerator.cs b/src/Microsoft.Tye.Core/KubernetesManifestGenerator.cs
index e9c27bd5..055c6cec 100644
--- a/src/Microsoft.Tye.Core/KubernetesManifestGenerator.cs
+++ b/src/Microsoft.Tye.Core/KubernetesManifestGenerator.cs
@@ -20,7 +20,7 @@ namespace Microsoft.Tye
             var root = new YamlMappingNode();
 
             root.Add("kind", "Ingress");
-            root.Add("apiVersion", "extensions/v1beta1");
+            root.Add("apiVersion", "networking.k8s.io/v1");
 
             var metadata = new YamlMappingNode();
             root.Add("metadata", metadata);
@@ -74,7 +74,10 @@ namespace Microsoft.Tye
 
                     var backend = new YamlMappingNode();
                     path.Add("backend", backend);
-                    backend.Add("serviceName", ingressRule.Service);
+                    var backendService = new YamlMappingNode();
+                    backend.Add("service", backendService);
+
+                    backendService.Add("name", ingressRule.Service);
 
                     var service = application.Services.FirstOrDefault(s => s.Name == ingressRule.Service);
                     if (service is null)
@@ -88,7 +91,11 @@ namespace Microsoft.Tye
                         throw new InvalidOperationException($"Could not resolve an http binding for service '{service.Name}'.");
                     }
 
-                    backend.Add("servicePort", (binding.Port ?? 80).ToString(CultureInfo.InvariantCulture));
+                    var backendPort = new YamlMappingNode();
+
+                    backendService.Add("port", backendPort);
+
+                    backendPort.Add("number", (binding.Port ?? 80).ToString(CultureInfo.InvariantCulture));
 
                     // Tye implements path matching similar to this example:
                     // https://kubernetes.github.io/ingress-nginx/examples/rewrite/
@@ -111,6 +118,9 @@ namespace Microsoft.Tye
                             path.Add("path", regex);
                         }
                     }
+
+                    // Only support prefix matching for now
+                    path.Add("pathType", "Prefix");
                 }
             }
 
diff --git a/src/Microsoft.Tye.Core/ValidateIngressStep.cs b/src/Microsoft.Tye.Core/ValidateIngressStep.cs
index 70a4a1cc..55e20c86 100644
--- a/src/Microsoft.Tye.Core/ValidateIngressStep.cs
+++ b/src/Microsoft.Tye.Core/ValidateIngressStep.cs
@@ -140,21 +140,20 @@ namespace Microsoft.Tye
             else
             {
                 // If we get here then we should deploy the ingress controller.
+
+                // For some reason, the first time we apply the ingress controller, an exception is thrown
+                // saying "ingress-nginx-admission-create" is invalid. Therefore, we are going to blindly assume the
+                // controller successfully ran.
+
                 output.WriteDebugLine($"Running 'kubectl apply'");
                 output.WriteCommandLine("kubectl", $"apply -f \"https://aka.ms/tye/ingress/deploy\"");
                 var capture = output.Capture();
                 var exitCode = await Process.ExecuteAsync(
                     $"kubectl",
                     $"apply -f \"https://aka.ms/tye/ingress/deploy\"",
-                    System.Environment.CurrentDirectory,
-                    stdOut: capture.StdOut,
-                    stdErr: capture.StdErr);
+                    System.Environment.CurrentDirectory);
 
                 output.WriteDebugLine($"Done running 'kubectl apply' exit code: {exitCode}");
-                if (exitCode != 0)
-                {
-                    throw new CommandException("'kubectl apply' failed.");
-                }
 
                 output.WriteInfoLine($"Waiting for ingress-nginx controller to start.");
 
@@ -162,7 +161,7 @@ namespace Microsoft.Tye
                 // after creating the controller will fail if the webhook isn't ready.
                 //
                 // Internal error occurred: failed calling webhook "validate.nginx.ingress.kubernetes.io": 
-                // Post https://ingress-nginx-controller-admission.ingress-nginx.svc:443/extensions/v1beta1/ingresses?timeout=30s:
+                // Post https://ingress-nginx-controller-admission.ingress-nginx.svc:443/networking.k8s.io/v1/ingresses?timeout=30s:
                 // dial tcp 10.0.31.130:443: connect: connection refused
                 //
                 // Unfortunately this is the likely case for us.
diff --git a/test/E2ETest/testassets/generate/apps-with-ingress.yaml b/test/E2ETest/testassets/generate/apps-with-ingress.yaml
index 1739d308..e8cbbe05 100644
--- a/test/E2ETest/testassets/generate/apps-with-ingress.yaml
+++ b/test/E2ETest/testassets/generate/apps-with-ingress.yaml
@@ -125,7 +125,7 @@ spec:
 ...
 ---
 kind: Ingress
-apiVersion: extensions/v1beta1
+apiVersion: networking.k8s.io/v1
 metadata:
   name: ingress
   annotations:
@@ -138,25 +138,37 @@ spec:
   - http:
       paths:
       - backend:
-          serviceName: appa
-          servicePort: 80
+          service:
+            name: appa
+            port:
+              number: 80
         path: /A(/|$)(.*)
+        pathType: Prefix
       - backend:
-          serviceName: appb
-          servicePort: 80
+          service:
+            name: appb
+            port:
+              number: 80
         path: /B(/|$)(.*)
+        pathType: Prefix
   - host: a.example.com
     http:
       paths:
       - backend:
-          serviceName: appa
-          servicePort: 80
+          service:
+            name: appa
+            port:
+              number: 80
         path: /()(.*)
+        pathType: Prefix
   - host: b.example.com
     http:
       paths:
       - backend:
-          serviceName: appb
-          servicePort: 80
+          service:
+            name: appb
+            port:
+              number: 80
         path: /()(.*)
+        pathType: Prefix
 ...