diff --git a/CliFx.Tests/ConversionSpecs.cs b/CliFx.Tests/ConversionSpecs.cs
index b58c550..7e182bc 100644
--- a/CliFx.Tests/ConversionSpecs.cs
+++ b/CliFx.Tests/ConversionSpecs.cs
@@ -946,5 +946,48 @@ public class Command : ICommand
             exitCode.Should().NotBe(0);
             stdErr.Should().Contain("Hello world");
         }
+
+        [Fact]
+        public async Task Parameter_or_option_value_conversion_fails_if_the_static_parse_method_throws()
+        {
+            // Arrange
+            var commandType = DynamicCommandBuilder.Compile(
+                // language=cs
+                @"
+public class CustomType
+{
+    public string Value { get; }
+    
+    private CustomType(string value) => Value = value;
+    
+    public static CustomType Parse(string value) => throw new Exception(""Hello world"");
+}
+
+[Command]
+public class Command : ICommand
+{
+    [CommandOption('f')]
+    public CustomType Foo { get; set; }
+    
+    public ValueTask ExecuteAsync(IConsole console) => default;
+}
+");
+            var application = new CliApplicationBuilder()
+                .AddCommand(commandType)
+                .UseConsole(FakeConsole)
+                .Build();
+
+            // Act
+            var exitCode = await application.RunAsync(
+                new[] {"-f", "bar"},
+                new Dictionary<string, string>()
+            );
+
+            var stdErr = FakeConsole.ReadErrorString();
+
+            // Assert
+            exitCode.Should().NotBe(0);
+            stdErr.Should().Contain("Hello world");
+        }
     }
 }
\ No newline at end of file
diff --git a/CliFx/CommandBinder.cs b/CliFx/CommandBinder.cs
index e527868..e5868b6 100644
--- a/CliFx/CommandBinder.cs
+++ b/CliFx/CommandBinder.cs
@@ -2,6 +2,7 @@
 using System.Collections.Generic;
 using System.Globalization;
 using System.Linq;
+using System.Reflection;
 using CliFx.Exceptions;
 using CliFx.Extensibility;
 using CliFx.Infrastructure;
@@ -161,12 +162,18 @@ namespace CliFx
             }
             catch (Exception ex) when (ex is not CliFxException) // don't wrap CliFxException
             {
+                // We use reflection-based invocation which can throw TargetInvocationException.
+                // Unwrap these exceptions to provide a more user-friendly error message.
+                var errorMessage = ex is TargetInvocationException invokeEx
+                    ? invokeEx.InnerException?.Message ?? invokeEx.Message
+                    : ex.Message;
+
                 throw CliFxException.UserError(
                     $"{memberSchema.GetKind()} {memberSchema.GetFormattedIdentifier()} cannot be set from provided argument(s):" +
                     Environment.NewLine +
                     rawValues.Select(v => '<' + v + '>').JoinToString(" ") +
                     Environment.NewLine +
-                    $"Error: {ex.Message}",
+                    $"Error: {errorMessage}",
                     ex
                 );
             }