diff --git a/tests/Resend.Webhooks.Tests/WebhookOutOfOrderTests.cs b/tests/Resend.Webhooks.Tests/WebhookOutOfOrderTests.cs
new file mode 100644
index 0000000..6844b38
--- /dev/null
+++ b/tests/Resend.Webhooks.Tests/WebhookOutOfOrderTests.cs
@@ -0,0 +1,79 @@
+using System.Text.Json;
+
+namespace Resend.Webhooks.Tests;
+
+/// <summary />
+public class WebhookOutOfOrderTests
+{
+    /// <summary />
+    /// <remarks>
+    /// Real Resend payloads serialize <c>type</c> last (after <c>created_at</c>
+    /// and <c>data</c>); the converter must not assume <c>type</c> comes first.
+    /// </remarks>
+    [Fact]
+    public void EmailEventTypeLastDeserializes()
+    {
+        var json = """
+        {
+          "created_at": "2026-07-09T18:23:37.867Z",
+          "data": {
+            "created_at": "2026-07-09T18:23:37.236Z",
+            "email_id": "c4bd0130-17f1-4e49-90bc-856308df9bb5",
+            "failed": { "reason": "domain_not_verified" },
+            "from": "Acme <onboarding@resend.dev>",
+            "subject": "Test",
+            "template_id": "2dc48b66-eef5-4601-b509-ca33f3e10b60",
+            "to": [ "to@example.com" ]
+          },
+          "type": "email.failed"
+        }
+        """;
+
+        var evt = JsonSerializer.Deserialize<WebhookEvent>( json );
+
+        Assert.NotNull( evt );
+        Assert.Equal( WebhookEventType.EmailFailed, evt.EventType );
+
+        var data = evt.DataAs<EmailEventData>();
+        Assert.Equal( "domain_not_verified", data.Failed?.Reason );
+        Assert.Equal( "2dc48b66-eef5-4601-b509-ca33f3e10b60", data.TemplateId );
+    }
+
+
+    /// <summary />
+    /// <remarks>Contact events serialize <c>created_at</c> before <c>type</c>.</remarks>
+    [Fact]
+    public void ContactEventCreatedAtFirstDeserializes()
+    {
+        var json = """
+        {
+          "created_at": "2026-07-09T18:23:37.867Z",
+          "type": "contact.created",
+          "data": {
+            "id": "e169aa45-1ecf-4183-9955-b1499d5701d3",
+            "created_at": "2026-07-09T18:23:37.236Z",
+            "updated_at": "2026-07-09T18:23:37.236Z",
+            "email": "to@example.com",
+            "unsubscribed": false
+          }
+        }
+        """;
+
+        var evt = JsonSerializer.Deserialize<WebhookEvent>( json );
+
+        Assert.NotNull( evt );
+        Assert.Equal( WebhookEventType.ContactCreated, evt.EventType );
+        Assert.Equal( "to@example.com", evt.DataAs<ContactEventData>().Email );
+    }
+
+
+    /// <summary />
+    [Theory]
+    [InlineData( """{ "type": "email.sent", "type": "email.sent", "created_at": "2026-07-09T18:23:37.867Z", "data": {} }""" )]
+    [InlineData( """{ "type": "email.sent", "created_at": "2026-07-09T18:23:37.867Z" }""" )]
+    [InlineData( """{ "type": "email.sent", "created_at": "2026-07-09T18:23:37.867Z", "data": {}, "extra": 1 }""" )]
+    public void MalformedEnvelopeThrows( string json )
+    {
+        Assert.ThrowsAny<JsonException>( () => JsonSerializer.Deserialize<WebhookEvent>( json ) );
+    }
+}
diff --git a/tools/Resend.Cli/Email/EmailSendCommand.cs b/tools/Resend.Cli/Email/EmailSendCommand.cs
index 11b4c08..4484cc3 100644
--- a/tools/Resend.Cli/Email/EmailSendCommand.cs
+++ b/tools/Resend.Cli/Email/EmailSendCommand.cs
@@ -122,7 +122,9 @@ public async Task<int> OnExecuteAsync()
          */
         if ( this.Verbose == true )
         {
-            Console.WriteLine( "From: {0}", message.From.Email );
+            if ( message.From != null )
+                Console.WriteLine( "From: {0}", message.From.Email );
+
             Console.WriteLine( "  To: {0}", string.Join( ", ", message.To ) );
             Console.WriteLine( "Subj: {0}", message.Subject );