diff --git a/src/Tools/dotnet-user-jwts/src/Helpers/DevJwtCliHelpers.cs b/src/Tools/dotnet-user-jwts/src/Helpers/DevJwtCliHelpers.cs
index 999d5e751461f7768a49e06ac75bbb6124d486b9..7a7dc7541c329dac6d4c241b3b0ba68396ed8dda 100644
--- a/src/Tools/dotnet-user-jwts/src/Helpers/DevJwtCliHelpers.cs
+++ b/src/Tools/dotnet-user-jwts/src/Helpers/DevJwtCliHelpers.cs
@@ -114,13 +114,19 @@ internal static class DevJwtCliHelpers
         ArgumentException.ThrowIfNullOrEmpty(nameof(project));
 
         var launchSettingsFilePath = Path.Combine(Path.GetDirectoryName(project)!, "Properties", "launchSettings.json");
-        var applicationUrls = new List<string>();
+        var applicationUrls = new HashSet<string>();
         if (File.Exists(launchSettingsFilePath))
         {
             using var launchSettingsFileStream = new FileStream(launchSettingsFilePath, FileMode.Open, FileAccess.Read);
             if (launchSettingsFileStream.Length > 0)
             {
                 var launchSettingsJson = JsonDocument.Parse(launchSettingsFileStream);
+
+                if (ExtractIISExpressUrlFromProfile(launchSettingsJson.RootElement) is { } iisUrls)
+                {
+                    applicationUrls.UnionWith(iisUrls);
+                }
+
                 if (launchSettingsJson.RootElement.TryGetProperty("profiles", out var profiles))
                 {
                     var profilesEnumerator = profiles.EnumerateObject();
@@ -128,25 +134,20 @@ internal static class DevJwtCliHelpers
                     {
                         if (ExtractKestrelUrlsFromProfile(profile) is { } kestrelUrls)
                         {
-                            applicationUrls.AddRange(kestrelUrls);
-                        }
-
-                        if (ExtractIISExpressUrlFromProfile(profile) is { } iisUrls)
-                        {
-                            applicationUrls.AddRange(iisUrls);
+                            applicationUrls.UnionWith(kestrelUrls);
                         }
                     }
                 }
             }
         }
 
-        return applicationUrls;
+        return applicationUrls.ToList();
 
-        static List<string> ExtractIISExpressUrlFromProfile(JsonProperty profile)
+        static List<string> ExtractIISExpressUrlFromProfile(JsonElement rootElement)
         {
-            if (profile.NameEquals("iisSettings"))
+            if (rootElement.TryGetProperty("iisSettings", out var iisSettings))
             {
-                if (profile.Value.TryGetProperty("iisExpress", out var iisExpress))
+                if (iisSettings.TryGetProperty("iisExpress", out var iisExpress))
                 {
                     List<string> iisUrls = new();
                     if (iisExpress.TryGetProperty("applicationUrl", out var iisUrl))
diff --git a/src/Tools/dotnet-user-jwts/test/UserJwtsTestFixture.cs b/src/Tools/dotnet-user-jwts/test/UserJwtsTestFixture.cs
index d3af1030c3edb397d4b280188e2447d3011a4931..c4364d33cb020295eb32cb4a5fbc543cde96194e 100644
--- a/src/Tools/dotnet-user-jwts/test/UserJwtsTestFixture.cs
+++ b/src/Tools/dotnet-user-jwts/test/UserJwtsTestFixture.cs
@@ -25,16 +25,16 @@ public class UserJwtsTestFixture : IDisposable
 
     private const string LaunchSettingsTemplate = @"
 {
+  ""iisSettings"": {
+    ""windowsAuthentication"": false,
+    ""anonymousAuthentication"": true,
+    ""iisExpress"": {
+      ""applicationUrl"": ""http://localhost:23528"",
+      ""sslPort"": 44395
+    }
+  },
   ""profiles"": {
-    ""iisSettings"": {
-        ""windowsAuthentication"": false,
-        ""anonymousAuthentication"": true,
-        ""iisExpress"": {
-            ""applicationUrl"": ""http://localhost:23528"",
-            ""sslPort"": 44395
-        }
-    },
-    ""HttpApiSampleApp"": {
+    ""HttpWebApp"": {
       ""commandName"": ""Project"",
       ""dotnetRunMessages"": true,
       ""launchBrowser"": true,
@@ -42,6 +42,22 @@ public class UserJwtsTestFixture : IDisposable
       ""environmentVariables"": {
         ""ASPNETCORE_ENVIRONMENT"": ""Development""
       }
+    },
+    ""HttpsOnly"": {
+      ""commandName"": ""Project"",
+      ""dotnetRunMessages"": true,
+      ""launchBrowser"": true,
+      ""applicationUrl"": ""https://localhost:5001"",
+      ""environmentVariables"": {
+        ""ASPNETCORE_ENVIRONMENT"": ""Development""
+      }
+    },
+    ""IIS Express"": {
+      ""commandName"": ""IISExpress"",
+      ""launchBrowser"": true,
+      ""environmentVariables"": {
+        ""ASPNETCORE_ENVIRONMENT"": ""Development""
+      }
     }
   }
 }";