diff --git a/CodeConverter/CSharp/ExpressionNodeVisitor.cs b/CodeConverter/CSharp/ExpressionNodeVisitor.cs
index dc1eb31e4..f35085ccf 100644
--- a/CodeConverter/CSharp/ExpressionNodeVisitor.cs
+++ b/CodeConverter/CSharp/ExpressionNodeVisitor.cs
@@ -2062,7 +2062,15 @@ private async Task<CSharpSyntaxNode> SubstituteVisualBasicMethodOrNullAsync(VBSy
             }
         }
 
-        if (SimpleMethodReplacement.TryGet(symbol, out var methodReplacement) &&
+        if (cSharpSyntaxNode == null && symbol is IMethodSymbol methodSymbol &&
+            Replacements.MsgBoxReplacement.IsBestMsgBoxMatch(methodSymbol))
+        {
+            var arguments = await ConvertArgumentsAsync(node.ArgumentList);
+            var msgBoxReplacement = new Replacements.MsgBoxReplacement(methodSymbol, arguments.ToList(), _semanticModel, _extraUsingDirectives, _visualBasicEqualityComparison);
+            cSharpSyntaxNode = msgBoxReplacement.Replace();
+        }
+
+        if (cSharpSyntaxNode == null && SimpleMethodReplacement.TryGet(symbol, out var methodReplacement) &&
             methodReplacement.ReplaceIfMatches(symbol, await ConvertArgumentsAsync(node.ArgumentList), false) is {} csExpression) {
             cSharpSyntaxNode = csExpression;
         }
diff --git a/CodeConverter/CSharp/Replacements/MsgBoxReplacement.cs b/CodeConverter/CSharp/Replacements/MsgBoxReplacement.cs
new file mode 100644
index 000000000..40b97b201
--- /dev/null
+++ b/CodeConverter/CSharp/Replacements/MsgBoxReplacement.cs
@@ -0,0 +1,137 @@
+using System.Collections.Generic;
+using System.Linq;
+using Microsoft.CodeAnalysis;
+using Microsoft.CodeAnalysis.CSharp;
+using Microsoft.CodeAnalysis.CSharp.Syntax;
+
+namespace ICSharpCode.CodeConverter.CSharp.Replacements
+{
+    internal class MsgBoxReplacement
+    {
+        private readonly IMethodSymbol _symbol;
+        private readonly IReadOnlyCollection<ArgumentSyntax> _arguments;
+        private readonly SemanticModel _semanticModel;
+        private readonly HashSet<string> _extraUsingDirectives;
+        private readonly VisualBasicEqualityComparison _visualBasicEqualityComparison;
+
+        public MsgBoxReplacement(IMethodSymbol symbol, IReadOnlyCollection<ArgumentSyntax> arguments, SemanticModel semanticModel, HashSet<string> extraUsingDirectives, VisualBasicEqualityComparison visualBasicEqualityComparison)
+        {
+            _symbol = symbol;
+            _arguments = arguments;
+            _semanticModel = semanticModel;
+            _extraUsingDirectives = extraUsingDirectives;
+            _visualBasicEqualityComparison = visualBasicEqualityComparison;
+        }
+
+        public ExpressionSyntax Replace()
+        {
+            var (prompt, style, title) = GetMsgBoxArguments();
+            if (prompt == null) return null; // Prompt is required
+
+            var (messageBoxButtons, messageBoxIcon) = ConvertStyle(style);
+            if (messageBoxButtons == null && messageBoxIcon == null && style != null)
+            {
+                // Could not convert style, fallback to default
+                return null;
+            }
+
+            _extraUsingDirectives.Add("System.Windows.Forms");
+
+            var showExpression = SyntaxFactory.MemberAccessExpression(
+                SyntaxKind.SimpleMemberAccessExpression,
+                SyntaxFactory.IdentifierName("MessageBox"),
+                SyntaxFactory.IdentifierName("Show")
+            );
+
+            var newArguments = new List<ArgumentSyntax>
+            {
+                prompt
+            };
+
+            if (title != null)
+            {
+                newArguments.Add(title);
+            } else {
+                newArguments.Add(SyntaxFactory.Argument(SyntaxFactory.LiteralExpression(SyntaxKind.StringLiteralExpression, SyntaxFactory.Literal(""))));
+            }
+
+            newArguments.Add(SyntaxFactory.Argument(messageBoxButtons ?? MemberAccess("OK")));
+
+            if (messageBoxIcon != null)
+            {
+                newArguments.Add(SyntaxFactory.Argument(messageBoxIcon));
+            }
+
+            return SyntaxFactory.InvocationExpression(showExpression, SyntaxFactory.ArgumentList(SyntaxFactory.SeparatedList(newArguments)));
+        }
+
+        private (ArgumentSyntax Prompt, ArgumentSyntax Buttons, ArgumentSyntax Title) GetMsgBoxArguments()
+        {
+            var args = _arguments.ToList();
+            var prompt = args.Count > 0 ? args[0] : null;
+            var buttons = args.Count > 1 ? args[1] : null;
+            var title = args.Count > 2 ? args[2] : null;
+            return (prompt, buttons, title);
+        }
+
+        private (ExpressionSyntax Buttons, ExpressionSyntax Icon) ConvertStyle(ArgumentSyntax styleArgument)
+        {
+            if (styleArgument == null)
+            {
+                return (MemberAccess("OK"), null);
+            }
+
+            var styleExpression = styleArgument.Expression;
+            var constantValue = _semanticModel.GetConstantValue(styleExpression);
+
+            if (!constantValue.HasValue)
+            {
+                // If we can't determine the style at compile time, we can't convert it.
+                // Fallback to Interaction.MsgBox will be handled by the caller.
+                return (null, null);
+            }
+
+            var styleValue = (int)constantValue.Value;
+
+            var buttons = GetMessageBoxButtons(styleValue);
+            var icon = GetMessageBoxIcon(styleValue);
+
+            return (buttons, icon);
+        }
+
+        private ExpressionSyntax GetMessageBoxButtons(int style)
+        {
+            if ((style & 0x1) == 0x1) return MemberAccess("OKCancel");
+            if ((style & 0x2) == 0x2) return MemberAccess("AbortRetryIgnore");
+            if ((style & 0x3) == 0x3) return MemberAccess("YesNoCancel");
+            if ((style & 0x4) == 0x4) return MemberAccess("YesNo");
+            if ((style & 0x5) == 0x5) return MemberAccess("RetryCancel");
+            return MemberAccess("OK");
+        }
+
+        private ExpressionSyntax GetMessageBoxIcon(int style)
+        {
+            if ((style & 0x10) == 0x10) return MemberAccess("Critical", "MessageBoxIcon");
+            if ((style & 0x20) == 0x20) return MemberAccess("Question", "MessageBoxIcon");
+            if ((style & 0x30) == 0x30) return MemberAccess("Exclamation", "MessageBoxIcon");
+            if ((style & 0x40) == 0x40) return MemberAccess("Information", "MessageBoxIcon");
+            return null;
+        }
+
+        private ExpressionSyntax MemberAccess(string memberName, string typeName = "MessageBoxButtons")
+        {
+            return SyntaxFactory.MemberAccessExpression(
+                SyntaxKind.SimpleMemberAccessExpression,
+                SyntaxFactory.IdentifierName(typeName),
+                SyntaxFactory.IdentifierName(memberName)
+            );
+        }
+
+        public static bool IsBestMsgBoxMatch(IMethodSymbol symbol)
+        {
+            return symbol?.ContainingType?.Name == "Interaction" &&
+                   symbol.Name == "MsgBox" &&
+                   symbol.ContainingNamespace?.ToDisplayString() == "Microsoft.VisualBasic";
+        }
+    }
+}
diff --git a/CodeConverter/CSharp/TypeMappings.cs b/CodeConverter/CSharp/TypeMappings.cs
new file mode 100644
index 000000000..f8588cd13
--- /dev/null
+++ b/CodeConverter/CSharp/TypeMappings.cs
@@ -0,0 +1,12 @@
+using System.Collections.Generic;
+
+namespace ICSharpCode.CodeConverter.CSharp
+{
+    internal static class TypeMappings
+    {
+        public static readonly IReadOnlyDictionary<string, string> VbToCs = new Dictionary<string, string>
+        {
+            { "Microsoft.VisualBasic.MsgBoxResult", "System.Windows.Forms.DialogResult" }
+        };
+    }
+}
diff --git a/Tests/CSharp/StatementTests/MethodStatementTests.cs b/Tests/CSharp/StatementTests/MethodStatementTests.cs
index b2f39e433..6a3e093dd 100644
--- a/Tests/CSharp/StatementTests/MethodStatementTests.cs
+++ b/Tests/CSharp/StatementTests/MethodStatementTests.cs
@@ -1671,6 +1671,33 @@ public object Func()
 
         return FuncRet;
     }
+}");
+    }
+
+    [Fact]
+    public async Task TestMsgBoxToMessageBoxConversionAsync()
+    {
+        await TestConversionVisualBasicToCSharpAsync(
+            @"Class TestClass
+    Private Sub TestMethod(ByVal sMLS As String)
+        Dim MsgBoxRet As MsgBoxResult
+        MsgBoxRet = MsgBox(sMLS, MsgBoxStyle.Question Or MsgBoxStyle.YesNo, ""Title"")
+        If MsgBoxRet = MsgBoxResult.Yes Then
+        End If
+    End Sub
+End Class",
+            @"using System.Windows.Forms;
+
+internal partial class TestClass
+{
+    private void TestMethod(string sMLS)
+    {
+        DialogResult MsgBoxRet;
+        MsgBoxRet = MessageBox.Show(sMLS, ""Title"", MessageBoxButtons.YesNo, MessageBoxIcon.Question);
+        if (MsgBoxRet == DialogResult.Yes)
+        {
+        }
+    }
 }");
     }
 }
\ No newline at end of file