My client is using iCloud Mail with his custom domain and he communicated with many govt organizations which seem to all be using Barracuda Email Protection for their spam prevention. I have properly configured his SPF, DKIM & DMARC DNS records however his emails were still being rejected. (Email header below) I contacted Barracuda support with the email header and they replied saying that the emails were rejected becuase Apple Mail has missing PTR records. I have sent dozens of emails for testing and looking at all their headers I can see (ms-asmtp-me-k8s.p00.prod.me.com [17.57.154.37]) which does not have a PTR record. ----FULL EMAIL HEADER WITH 3RD PARTY DOMAINS REMOVED----- <recipient_email_address>: host d329469a.ess.barracudanetworks.com[209.222.82.255] said: 550 permanent failure for one or more recipients (recipient_email_address:blocked) (in reply to end of DATA command) Reporting-MTA: dns; p00-icloudmta-asmtp-us-west-3a-100-percent-10.p00-icloudmta-asmtp-vip.icloud-mail-production.svc.kube.us-west-3a.k8s.cloud.apple.com X-Postfix-Queue-ID: 8979C18013F8 X-Postfix-Sender: rfc822; sender_email_address Arrival-Date: Thu, 20 Mar 2025 12:30:05 +0000 (UTC) Final-Recipient: rfc822; @****** Original-Recipient: rfc822;recipient_email_address Action: failed Status: 5.0.0 Remote-MTA: dns; d329469a.ess.barracudanetworks.com Diagnostic-Code: smtp; 550 permanent failure for one or more recipients (recipient_email_address:blocked) Return-Path: <sender_email_address> DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=sender_domain; s=sig1; bh=CyUt/U7mIHwXB5OQctPjRH/OxLH7GsLR54JjGuRkj9Y=; h=From:Message-Id:Content-Type:Mime-Version:Subject:Date:To:x-icloud-hme; b=hwEbggsctiCRlMlEgovBTjB/0sPRCb2k+1wzHRZ2dZNrZdOqvFSNWU+Aki9Bl8nfv eEOoXz5qWxO2b2rEBl08lmRQ3hCyroayIn4keBRrgkxL1uu4zMTaDUHyau2vVnzC3h ZmwQtQxiu7QvTS/Sp8jjJ/niOPSzlfhphqMxnQAZi/jmJGcZPadT8K+7+PhRllVnI+ TElJarN1ORQu+CaPGhEs9/F7AIcjJNemnVg1cude7EUuO9va8ou49oFExWTLt7YSMl s+88hxxGu3GugD3eBnitzVo7s7/O9qkIbDUjk3w04/p/VOJ+35Mvi+v/zB9brpYwC1 B4dZP+AhwJDYA== Received: from smtpclient.apple (ms-asmtp-me-k8s.p00.prod.me.com [17.57.154.37]) by p00-icloudmta-asmtp-us-west-3a-100-percent-10.p00-icloudmta-asmtp-vip.icloud-mail-production.svc.kube.us-west-3a.k8s.cloud.apple.com (Postfix) with ESMTPSA id 8979C18013F8; Thu, 20 Mar 2025 12:30:05 +0000 (UTC) From: Marcel Brunel <sender_email_address> Message-Id: <2E8D69EA-FCA6-4F5D-9D42-22A955C073F6@sender_domain> Content-Type: multipart/alternative; boundary="Apple-Mail=_F9AC7D29-8520-4B25-9362-950CB20ADEC5" Mime-Version: 1.0 (Mac OS X Mail 16.0 (3826.400.131.1.6)) Subject: Re: [EXTERNAL] - Re: Brunel - 2024 taxes Date: Thu, 20 Mar 2025 07:29:27 -0500 In-Reply-To: <SA0PR18MB350300DE7274C018F66EEA24F2D82@SA0PR18MB3503_namprd18_prod_outlook_com> To: Troy Womack <recipient_email_address> References: <SA0PR18MB350314D0B88E283C5C8E1BB6F2DE2@SA0PR18MB3503_namprd18_prod_outlook_com> <9B337A3E-D373-48C5-816F-C1884BDA6F42@sender_domain> <SA0PR18MB350341A7172E8632D018A910F2D82@SA0PR18MB3503_namprd18_prod_outlook_com> <SA0PR18MB350300DE7274C018F66EEA24F2D82@SA0PR18MB3503_namprd18_prod_outlook_com> X-Mailer: Apple Mail (2.3826.400.131.1.6) X-Proofpoint-ORIG-GUID: uqebp2OIbPqBr3dYsAxdFVkCNbM5Cxyl X-Proofpoint-GUID: uqebp2OIbPqBr3dYsAxdFVkCNbM5Cxyl X-Proofpoint-Virus-Version: vendor=baseguard engine=ICAP:2.0.293,Aquarius:18.0.1093,Hydra:6.0.680,FMLib:17.12.68.34 definitions=2025-03-20_03,2025-03-19_01,2024-11-22_01 X-Proofpoint-Spam-Details: rule=notspam policy=default score=0 bulkscore=0 clxscore=1030 suspectscore=0 mlxlogscore=999 mlxscore=0 phishscore=0 malwarescore=0 spamscore=0 adultscore=0 classifier=spam adjust=0 reason=mlx scancount=1 engine=8.19.0-2411120000 definitions=main-2503200077