diff --git a/src/Containers/Microsoft.NET.Build.Containers/ContainerHelpers.cs b/src/Containers/Microsoft.NET.Build.Containers/ContainerHelpers.cs
index 34cda5315b1e..c27d1ea25874 100644
--- a/src/Containers/Microsoft.NET.Build.Containers/ContainerHelpers.cs
+++ b/src/Containers/Microsoft.NET.Build.Containers/ContainerHelpers.cs
@@ -9,6 +9,7 @@
 using System.Diagnostics.CodeAnalysis;
 #endif
 using System.Text;
+using System.Text.Json.Nodes;
 using System.Text.RegularExpressions;
 using Microsoft.NET.Build.Containers.Resources;
 
@@ -143,13 +144,27 @@ internal static bool IsValidImageTag(string imageTag)
         return ReferenceParser.anchoredTagRegexp.IsMatch(imageTag);
     }
 
+
     /// <summary>
     /// Given an already-validated registry domain, this is our hueristic to determine what HTTP protocol should be used to interact with it.
+    /// If the domain is localhost, we default to HTTP. Otherwise, we check the Docker config to see if the registry is marked as insecure.
     /// This is primarily for testing - in the real world almost all usage should be through HTTPS!
     /// </summary>
     internal static Uri TryExpandRegistryToUri(string alreadyValidatedDomain)
     {
-        var prefix = alreadyValidatedDomain.StartsWith("localhost", StringComparison.Ordinal) ? "http" : "https";
+        string prefix = "https";
+        if (alreadyValidatedDomain.StartsWith("localhost", StringComparison.Ordinal))
+        {
+            prefix = "http";
+        }
+
+        //check the docker config to see if the registry is marked as insecure
+        else if (DockerCli.IsInsecureRegistry(alreadyValidatedDomain))
+        {
+            prefix = "http";
+        }
+
+
         return new Uri($"{prefix}://{alreadyValidatedDomain}");
     }
 
diff --git a/src/Containers/Microsoft.NET.Build.Containers/LocalDaemons/DockerCli.cs b/src/Containers/Microsoft.NET.Build.Containers/LocalDaemons/DockerCli.cs
index b7b0733ad52a..fb0e09b87d5a 100644
--- a/src/Containers/Microsoft.NET.Build.Containers/LocalDaemons/DockerCli.cs
+++ b/src/Containers/Microsoft.NET.Build.Containers/LocalDaemons/DockerCli.cs
@@ -2,7 +2,9 @@
 // The .NET Foundation licenses this file to you under the MIT license.
 
 using System.Diagnostics;
+#if NET
 using System.Formats.Tar;
+#endif
 using System.Text.Json;
 using System.Text.Json.Nodes;
 using Microsoft.DotNet.Cli.Utils;
@@ -12,7 +14,10 @@
 namespace Microsoft.NET.Build.Containers;
 
 // Wraps the 'docker'/'podman' cli.
-internal sealed class DockerCli : ILocalRegistry
+internal sealed class DockerCli
+#if NET
+: ILocalRegistry
+#endif
 {
     public const string DockerCommand = "docker";
     public const string PodmanCommand = "podman";
@@ -21,7 +26,10 @@ internal sealed class DockerCli : ILocalRegistry
 
     private readonly ILogger _logger;
     private string? _command;
+
+#if NET
     private string? _fullCommandPath;
+#endif
 
     public DockerCli(string? command, ILoggerFactory loggerFactory)
     {
@@ -53,6 +61,7 @@ private static string FindFullPathFromPath(string command)
         return command;
     }
 
+#if NET
     private async ValueTask<string> FindFullCommandPath(CancellationToken cancellationToken)
     {
         if (_fullCommandPath != null)
@@ -164,6 +173,7 @@ public bool IsAvailable()
 
     public string? GetCommand()
         => GetCommandAsync(default).GetAwaiter().GetResult();
+#endif
 
     /// <summary>
     /// Gets docker configuration.
@@ -185,7 +195,6 @@ internal static JsonDocument GetDockerConfig()
             dockerCommand.CaptureStdErr();
             CommandResult dockerCommandResult = dockerCommand.Execute();
 
-
             if (dockerCommandResult.ExitCode != 0)
             {
                 throw new DockerLoadException(Resource.FormatString(
@@ -196,17 +205,68 @@ internal static JsonDocument GetDockerConfig()
             }
 
             return JsonDocument.Parse(dockerCommandResult.StdOut);
-
-
         }
         catch (Exception e) when (e is not DockerLoadException)
         {
             throw new DockerLoadException(Resource.FormatString(nameof(Strings.DockerInfoFailed_Ex), e.Message));
         }
     }
+    /// <summary>
+    /// Checks if the registry is marked as insecure in the docker/podman config.
+    /// </summary>
+    /// <param name="registryDomain"></param>
+    /// <returns></returns>
+    public static bool IsInsecureRegistry(string registryDomain)
+    {
+        try
+        {
+            //check the docker config to see if the registry is marked as insecure
+            var rootElement = GetDockerConfig().RootElement;
+
+            //for docker
+            if (rootElement.TryGetProperty("RegistryConfig", out var registryConfig) && registryConfig.ValueKind == JsonValueKind.Object)
+            {
+                if (registryConfig.TryGetProperty("IndexConfigs", out var indexConfigs) && indexConfigs.ValueKind == JsonValueKind.Object)
+                {
+                    foreach (var property in indexConfigs.EnumerateObject())
+                    {
+                        if (property.Value.ValueKind == JsonValueKind.Object && property.Value.TryGetProperty("Secure", out var secure) && !secure.GetBoolean())
+                        {
+                            if (property.Name.Equals(registryDomain, StringComparison.Ordinal))
+                            {
+                                return true;
+                            }
+                        }
+                    }
+                }
+            }
+
+            //for podman
+            if (rootElement.TryGetProperty("registries", out var registries) && registries.ValueKind == JsonValueKind.Object)
+            {
+                foreach (var property in registries.EnumerateObject())
+                {
+                    if (property.Value.ValueKind == JsonValueKind.Object && property.Value.TryGetProperty("Insecure", out var insecure) && insecure.GetBoolean())
+                    {
+                        if (property.Name.Equals(registryDomain, StringComparison.Ordinal))
+                        {
+                            return true;
+                        }
+                    }
+                }
+            }
+            return false;
+        }
+        catch (DockerLoadException)
+        {
+            //if docker load fails, we can't check the config so we assume the registry is secure
+            return false;
+        }
+    }
 
     private static void Proc_OutputDataReceived(object sender, DataReceivedEventArgs e) => throw new NotImplementedException();
 
+#if NET
     public static async Task WriteImageToStreamAsync(BuiltImage image, SourceImageReference sourceReference, DestinationImageReference destinationReference, Stream imageStream, CancellationToken cancellationToken)
     {
         cancellationToken.ThrowIfCancellationRequested();
@@ -312,6 +372,7 @@ await Task.WhenAll(
 
         return _command;
     }
+#endif
 
     private static bool IsPodmanAlias()
     {
@@ -333,6 +394,7 @@ private static bool IsPodmanAlias()
         }
     }
 
+#if NET
     private async Task<bool> TryRunVersionCommandAsync(string command, CancellationToken cancellationToken)
     {
         try
@@ -355,6 +417,7 @@ private async Task<bool> TryRunVersionCommandAsync(string command, CancellationT
             return false;
         }
     }
+#endif
 
     public override string ToString()
     {
diff --git a/src/Containers/Microsoft.NET.Build.Containers/Microsoft.NET.Build.Containers.csproj b/src/Containers/Microsoft.NET.Build.Containers/Microsoft.NET.Build.Containers.csproj
index 040677b24bf5..2c6b5818c1af 100644
--- a/src/Containers/Microsoft.NET.Build.Containers/Microsoft.NET.Build.Containers.csproj
+++ b/src/Containers/Microsoft.NET.Build.Containers/Microsoft.NET.Build.Containers.csproj
@@ -43,6 +43,8 @@
     <Compile Remove="**/*.*" />
     <Compile Include="ReferenceParser.cs" />
     <Compile Include="KnownStrings.cs" />
+    <Compile Include="DockerLoadException.cs" />
+    <Compile Include="LocalDaemons/DockerCli.cs" />
     <Compile Include="Tasks/ParseContainerProperties.cs" />
     <Compile Include="Tasks/CreateNewImage.Interface.cs" />
     <Compile Include="Tasks/CreateNewImageToolTask.cs" />