Cloudron rejects iCloud forwarding only when “Delete after forwarding” is enabled (SMTP 550 on MAIL FROM)
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Hello Cloudron Support,
I’m running Cloudron Mail on my server (mail.estudios507.com / IP 199.241.136.89). I’m trying to set up automatic forwarding from iCloud Mail to a mailbox hosted on Cloudron.
Setup:
• iCloud account: jackhasday@mac.com
• In iCloud.com (Mail Settings): forwarding to inbox@jackhasday.com (mailbox hosted on my Cloudron)
• Option enabled: “Delete messages after forwarding”Issue:
When “Delete messages after forwarding” is enabled, Cloudron rejects the forwarded message with an SMTP 550 error during the MAIL FROM command, following this pattern:550 Mail from domain '<domain>' is not allowed from your host (in reply to MAIL FROM command)
In the bounce messages I can see:
• Reporting-MTA: outbound.ms.icloud.com (iCloud is the system delivering the forwarded message)
• Return-Path / envelope-from: e.g. jack@estudios507.com or jack.jr@jardineshasday.com
• Final recipient: inbox@jackhasday.comKey behavior:
1. If I disable “Delete messages after forwarding” in iCloud, forwarding works and there is no bounce. However, I don’t want to use it this way because the messages that have already been forwarded remain stored in the iCloud mailbox, and there is no way to delete them automatically.
2. If the original email arriving at jackhasday@mac.com comes from external domains (for example Hotmail, gmail, etc), forwarding works fine even with delete enabled.
3. The bounce happens specifically when the original email arriving at jackhasday@mac.com comes from a domain that is also hosted on my Cloudron (for example estudios507.com, jardineshasday.com, and other customer domains hosted on this server). I understand the issue is limited to domains hosted on my own Cloudron, but I cannot make an exception or workaround based on that because most of those locally-hosted domains belong to customers who email me regularly. If those customers email jackhasday@mac.com for support or services, the forwarded message bounces and I never receive it in inbox@jackhasday.com.
4. The bounce only happens when iCloud is forwarding in “forward + delete” mode (the bounce shows X-Apple-Action: FORWARD_DISCARD/...).What I need:
• Identify which Cloudron restriction/policy is triggering “Mail from domain ‘X’ is not allowed from your host” in this scenario.
• Confirm whether there is a supported and safe way in Cloudron to allow this specific flow (forwarding from iCloud with delete enabled) without broadly weakening anti-spoofing protections.I can provide full bounce headers and/or server logs if needed.
Best regards,
Jack Hasday -
Hello @estudios507
Thank you for the detailed report. I will try to assist you to my best capabilities.
@estudios507 said in Cloudron rejects iCloud forwarding only when “Delete after forwarding” is enabled (SMTP 550 on MAIL FROM):
Identify which Cloudron restriction/policy is triggering “Mail from domain ‘X’ is not allowed from your host” in this scenario.
Regarding why this is happening.
When iCloud forwards messages in delete mode, iCloud uses the original sender’s MAIL FROM (envelope-from) unchanged instead of rewriting it. If that original sender domain is hosted on the same Cloudron server, Cloudron sees an external connection (from iCloud’s outbound IP) claiming to send mail from its own domain.
Cloudron treats that as spoofing and rejects it.
@estudios507 said in Cloudron rejects iCloud forwarding only when “Delete after forwarding” is enabled (SMTP 550 on MAIL FROM):
Confirm whether there is a supported and safe way in Cloudron to allow this specific flow (forwarding from iCloud with delete enabled) without broadly weakening anti-spoofing protections.
There is also another topic regarding this issue with iCloud, see: https://forum.cloudron.io/topic/1998/mail-error-after-sending-message-mail-from-domain-example-com-is-not-allowed-from-your-host
A fix is to add the iCloud servers to the domain A's SPF record.
Your current SPF record is:dig TXT estudios507.com +short "v=spf1 a:mail.estudios507.com include:_spf.safewebservices.com ~all"You can edit that to include apple:
"v=spf1 a:mail.estudios507.com include:_spf.safewebservices.com include:_spf.apple.com ~all"after that edit it can take some time to propagate, but this should resolve your issue.
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Below is a bounce generated when the original email was sent from jack@estudios507.com to jackhasday@mac.com, and then iCloud attempted to forward it (with “Delete after forwarding” enabled) to inbox@jackhasday.com. The forward was rejected by my Cloudron server:
This is a system-generated message to inform you that your email could not
be delivered to one or more recipients. Details of the email and the error are as follows:<inbox@jackhasday.com>: host mail.estudios507.com[199.241.136.89] said: 550 Mail from domain 'estudios507.com' is not allowed from your host (in reply to MAIL FROM command) Reporting-MTA: dns; outbound.ms.icloud.com X-Postfix-Queue-ID: 475EA180017D X-Postfix-Sender: rfc822; jack@estudios507.com Arrival-Date: Wed, 21 Jan 2026 19:07:34 +0000 (UTC) Final-Recipient: rfc822; *****@************** Original-Recipient: rfc822;jackhasday@mac.com Action: failed Status: 5.0.0 Remote-MTA: dns; mail.estudios507.com Diagnostic-Code: smtp; 550 Mail from domain 'estudios507.com' is not allowed from your host Return-Path: <jack@estudios507.com> Received: from outbound.ms.icloud.com (unknown [127.0.0.2]) by p00-icloudmta-asmtp-us-west-3a-60-percent-4 (Postfix) with ESMTPS id 475EA180017D for <inbox@jackhasday.com>; Wed, 21 Jan 2026 19:07:34 +0000 (UTC) ARC-Seal: i=1; a=rsa-sha256; cv=none; d=icloud.com; s=arc-0513; b=S2yd6TLvBnhNOxNVHkkFXncFtr9aYrUkKvhEWh/ImSz5efDxug/Fzl/F71A6rPLpp+66oHQwMr3u2XKTDzJeduL7YAAFpe8uH6Qu3ret+RwD0ZbOro0DOkgS4oWh5OqHi17xuGnJ54kEppQvWrea2H5qgAMf/AH+vuu7VhC5k+YaHB6QdGFiBmG8M0OHqUR+9Ksufb9rK38Ll6x+Kjbxa7+ko34GOEZ4snUedwa/U6LyRClYDxUDIZI/5ySnBFaammMSXSkZQaXyl1+3Kek+IOr1oqVK0RvGvdjlloKC8tSOtST16/wxOm5fWqooRoX4vK18hv6i0ImYtQ4I21p32g== ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=icloud.com; s=arc-0513; h=from:to:subject:message-id:date:mime-version:content-type:dkim-signature; bh=uBdSC2KDIl7+AkVnH20TzbYC/UkYANx/BH9ehYm/0vE=; b=inlB4F04p2wQyhVJ8d1BGTIOrYc+mio1WQBnt/2RV3CZHZDvuGw/rrXk8n61ND8At/9RsuI7aJO0QByQ8LUnmv/Jy0VEsSnNzw1IRWfNhwhPxJ0tN/6xJM9HWyNIA+I93jz9FL8SxHHeZ12VPmEDDR2/h8qwEaCRuVNJRp8Z19cK3YgsUN7f0jOG3HgPrE39wJmdNJ83XfGc+qAJMwqwwvtVMWqTHD84ZN5wia/ZJ+CDjbMzRwKd86NS4esa6LaZ7RmzvpjUYMBY85aLw/NVfCo8w1l7b7djloSEXXsmYicl5PgZey4J/9yRnXKMLEjD2Eoc4HEhQbhXVt5n6EBfkQ== ARC-Authentication-Results: i=1; arc.icloud.com; arc=none; dmarc=pass header.from=estudios507.com; dkim=pass header.d=estudios507.com header.i=@estudios507.com header.b=Sv/1I+80; spf=pass (spf.icloud.com: domain of jack@estudios507.com designates 199.241.136.89 as permitted sender) smtp.mailfrom=jack@estudios507.com Received: from unknown (unknown [10.52.196.11]) by p00-icloudmta-asmtp-us-west-3a-60-percent-4 (Postfix) with SMTP id CD5CB18001A8 for <inbox@jackhasday.com>; Wed, 21 Jan 2026 19:07:33 +0000 (UTC) Received: from p00-icloudmta-smtpin-us-east-2d-100-percent-1 by p102-mailgateway-smtp-677754878b-94pct (mailgateway 2544B77) with SMTP id 46b248cb-85a3-4e75-8860-af40d23a0f87 for <jackhasday@mac.com>; Wed, 21 Jan 2026 19:07:33 GMT X-ICLOUD-MAIL-BWL: 1 X-Apple-Action: FORWARD_DISCARD/inbox@jackhasday.com Original-Recipient: rfc822;jackhasday@mac.com x-apple-request-uuid: 46b248cb-85a3-4e75-8860-af40d23a0f87 Received: from mail.estudios507.com (mail.estudios507.com [199.241.136.89]) by p00-icloudmta-smtpin-us-east-2d-100-percent-1 (Postfix) with ESMTPS id 34F59C00E91 for <jackhasday@mac.com>; Wed, 21 Jan 2026 19:07:28 +0000 (UTC) X-ICL-Info: GAtbRVYDBVFFSlVHSgQEUFUKE0oWX1gHVQoPB0UBD1tbS1JGVgEFVFtBX1cdVAsIFBoNNx1DQhcREAkETQABTBYWC1ceVAsHBg0TExFfRVdFTkgUF10WEBZEDBYbW14DBh0HDjhdVwFbGgkaWFhTDhpECxYRXBgHBg0TExFfRVdFTkgUF10WEgELWxoZWVpMEAoSAhxZWRFASVFZG19bQhEdWxILREMGHBYVQkgHGAEaFEYaEVQLXkJNU05MAXUgWEAkNTkdAlJEOEtPTHJyT0RMX0Y8BHdaN0xUQThVRRYAHQ8YCwUGVVsaCRpG X-ICL-Score: 2.33303302422 Authentication-Results: bimi.icloud.com; bimi=none X-ARC-Info: policy=fail; arc=none; r1=-20; r2=0 Authentication-Results: arc.icloud.com; arc=none Authentication-Results: dmarc.icloud.com; dmarc=pass header.from=estudios507.com X-DMARC-Policy: v=DMARC1; p=reject; pct=100 X-DMARC-Info: pass=pass; dmarc-policy=reject; s=r1; d=r1; pdomain=estudios507.com Authentication-Results: dkim-verifier.icloud.com; dkim=pass header.d=estudios507.com header.i=@estudios507.com header.b=Sv/1I+80 Received-SPF: pass (spf.icloud.com: domain of jack@estudios507.com designates 199.241.136.89 as permitted sender) receiver=spf.icloud.com; client-ip=199.241.136.89; helo=mail.estudios507.com; envelope-from=jack@estudios507.com Authentication-Results: spf.icloud.com; spf=pass (spf.icloud.com: domain of jack@estudios507.com designates 199.241.136.89 as permitted sender) smtp.mailfrom=jack@estudios507.com Received: (Haraka outbound); Wed, 21 Jan 2026 19:07:26 +0000 Authentication-Results: mail.estudios507.com; auth=pass (plain) From: E507 | Jack Hasday <jack@estudios507.com> Content-Type: multipart/alternative; boundary="Apple-Mail=_8AB95481-D215-4A19-A0CB-0090E0E79688" Mime-Version: 1.0 (Mac OS X Mail 16.0 \(3864.400.12\)) Subject: Test Message-Id: <745941CB-9BBA-401A-84BD-1591D4A8B526@estudios507.com> Date: Wed, 21 Jan 2026 14:07:14 -0500 To: Jack Hasday <jackhasday@mac.com> X-Mailer: Apple Mail (2.3864.400.12) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=estudios507.com; s=cloudron-026c7d; h=from:subject:date:message-id:to:mime-version; bh=y43DVsgG2sU95VoXJ0FNgPZl58lguq516l82fE0M9Ac=; b=Sv/1I+80bXdOtk7RYow8yU3V3UAfdSrSymfGzYLCdA9SO59/TTCEjGjLD1K7CuzMBLq39LGI1H D9Izniv7jegFHJP+B/FUSgjVj6kfdgu+7kbkLSvHIlNS5ottOgS2nxRCFRrKlnpwj4tioQcZupLH +pELZV5MT2SlDlW1ToSwE= X-Proofpoint-ORIG-GUID: lifheCblypm6Yf9Jas2NgnRYtz2szM_1 X-Proofpoint-GUID: lifheCblypm6Yf9Jas2NgnRYtz2szM_1 X-Proofpoint-Spam-Details-Enc: AW1haW4tMjYwMTIxMDE2MCBTYWx0ZWRfX4C54gR/nkgrb Jq9rzGCHrksr37sqEjTssH2rFfOa2+dKf9n9s8E4IcjjrmXCu3ybYQpKjnYVLUFgj9pvjBl0U1i KkTMyBkWAc4yOIoJvj0gc2X5nJdWY1YUPeR2rNWi2DB537QpcnkVkUZd50BltYhcGcC7jSdWHHH 75J7WCuM7BppM7fsK6h/lfizkvSsrdcitmj5sH0irsE3PKjMwbSWDJnoEjzurYjqTnR/DWStDYR sCkS/XuyjX899H0jr5C8up0+ba73z+TrEOvTqlZvU4cbesi2xSNYIprbV0LuA6+s6G8DTMyez1S nopO4LSNy4M8Ovwldtl X-JNJ: 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 X-Authority-Info-Out: v=2.4 cv=Y5f1cxeN c=1 sm=1 tr=0 ts=697123f6 cx=c_apl:c_apl_out:c_pps a=Ng/DTdlv9dYXrlarcUhKoA==:117 a=ry2iD/qIpUaetSALygwXCg==:17 a=vUbySO9Y5rIA:10 a=ulvbZRrZjisA:10 a=VkNPw1HP01LnGYTKEx00:22 a=8lJhZ5ieAAAA:8 a=wUyKfIghAAAA:20 a=OlGai0vOSlytd9CZm7AA:9 a=lqcHg5cX4UMA:10 a=PRpDppDLrCsA:10 a=QEXdDO2ut3YA:10 a=FDb1XksWRdYA:10 a=gP4qA3YHpW5r2j2eUlAA:9 a=OKjO5_YqkLUv6xfn:21 a=_W_S_7VecoQA:10 a=CjuIK1q_8ugA:10 a=HXjIzolwW10A:10 a=T6a71-JsGAwA:10 a=Vkyao1OQ-qhFCJ-NQpkk:22 X-Proofpoint-Virus-Version: X-Proofpoint-Spam-Details: rule=notspam policy=default score=0 spamscore=0 clxscore=1030 bulkscore=0 mlxlogscore=512 phishscore=0 malwarescore=0 suspectscore=0 mlxscore=0 adultscore=0 classifier=spam authscore=0 adjust=0 reason=mlx scancount=1 engine=8.22.0-2510240001 definitions=main-2601210160 X-JNJ: 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 -
Below is a second bounce generated when the original email was sent from jack.jr@jardineshasday.com to jackhasday@mac.com, and then iCloud attempted to forward it (with “Delete after forwarding” enabled) to inbox@jackhasday.com. The forward was also rejected by my Cloudron server:
This is a system-generated message to inform you that your email could not
be delivered to one or more recipients. Details of the email and the error are as follows:<inbox@jackhasday.com>: host mail.estudios507.com[199.241.136.89] said: 550 Mail from domain 'jardineshasday.com' is not allowed from your host (in reply to MAIL FROM command) Reporting-MTA: dns; outbound.ms.icloud.com X-Postfix-Queue-ID: 325F21800435 X-Postfix-Sender: rfc822; jack.jr@jardineshasday.com Arrival-Date: Wed, 21 Jan 2026 19:15:47 +0000 (UTC) Final-Recipient: rfc822; *****@************** Original-Recipient: rfc822;jackhasday@mac.com Action: failed Status: 5.0.0 Remote-MTA: dns; mail.estudios507.com Diagnostic-Code: smtp; 550 Mail from domain 'jardineshasday.com' is not allowed from your host Return-Path: <jack.jr@jardineshasday.com> Received: from outbound.ms.icloud.com (unknown [127.0.0.2]) by p00-icloudmta-asmtp-us-west-3a-20-percent-1 (Postfix) with ESMTPS id 325F21800435 for <inbox@jackhasday.com>; Wed, 21 Jan 2026 19:15:47 +0000 (UTC) ARC-Seal: i=1; a=rsa-sha256; cv=none; d=icloud.com; s=arc-0513; b=NwePU52YPB5g8CvhYlOZRV4RuLpPepXFXChfOBAHfjuskdDlU7U+gtyKSgqfFoQxW0ie00VK0/LMtdogYq7qu2Xikrz5yRwPbTSRLdT41WnsO0RVwNMfYvqJRCdvy66EeRPiWHwLg0Eu9trOA0SHcmFrJQ18Fbbozx/4iNznCHfypwVydXjj7LnsbZpB0y8iZ6xF5eWrs2JMnkiEijmRJksQ/4oBhYFMgM48tIzxWBmlmP/MECl/cUuiq+jQGETcZuAZE9LPx6iqHzxY8u199Uz8uIX9Z4LeC62IsXFpl+A0lAzcbvFNg/7WCjynmO3dR86Lu0c2o3VdyxM24b5G5g== ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=icloud.com; s=arc-0513; h=from:to:subject:message-id:date:mime-version:content-type:dkim-signature; bh=B8Rq7JfCpjn8orX4LKFaNcIdBzBmhpd4dlBrVjqXnPM=; b=h9YkNs4Phgpq/dvngLz8yMSPy5QLbqlcfr4pe7FTr11NBlWMbAH58s5/8uWsziQ3suyxOk6SjDI0/IcflrJVjJUQwSl1cABJ7ZIeDlUQIZGHH2nzhQF3Wns/D99TbuNhBDovINzTqgrgEbzv3GEwWFWu/CqIQl1r8PjqH3Y1lcebL7Pgnbw48XlvliW8nWUf2qHmIzEEncNAQVeVJ/Z2FLP3z3rxczRLaisE9lgVJwE7MhWUYpMA5fIsu2L9XJx0Y1hqOwp2lBW3lerjLjXiKPXmTnh/Hak2/9dSR8jDfm8RZKBO1hsmwn7iWSib/awzvbXWbbPeZgCOQBMyOqMIBg== ARC-Authentication-Results: i=1; arc.icloud.com; arc=none; dmarc=pass header.from=jardineshasday.com; dkim=pass header.d=jardineshasday.com header.i=@jardineshasday.com header.b=q+vfqcQe; spf=pass (spf.icloud.com: domain of jack.jr@jardineshasday.com designates 199.241.136.89 as permitted sender) smtp.mailfrom=jack.jr@jardineshasday.com Received: from unknown (unknown [10.52.196.11]) by p00-icloudmta-asmtp-us-west-3a-20-percent-1 (Postfix) with SMTP id AB65F1800411 for <inbox@jackhasday.com>; Wed, 21 Jan 2026 19:15:46 +0000 (UTC) Received: from p00-icloudmta-smtpin-us-west-1a-60-percent-39 by p102-mailgateway-smtp-677754878b-9bv27 (mailgateway 2544B77) with SMTP id 0a4cb2a5-6cf4-4a9c-9d3f-93212efa68da for <jackhasday@mac.com>; Wed, 21 Jan 2026 19:15:46 GMT X-Apple-Action: FORWARD_DISCARD/inbox@jackhasday.com Original-Recipient: rfc822;jackhasday@mac.com x-apple-request-uuid: 0a4cb2a5-6cf4-4a9c-9d3f-93212efa68da Received: from mail.estudios507.com (mail.estudios507.com [199.241.136.89]) by p00-icloudmta-smtpin-us-west-1a-60-percent-39 (Postfix) with ESMTPS id 19E7CC001CD for <jackhasday@mac.com>; Wed, 21 Jan 2026 19:15:38 +0000 (UTC) X-ICL-Info: GAtbRVYDBVFFSlVFSgQEUFUKE0oWX1gHVQoPB0UBD1tbS1JGVgEFVFtBX1cdVAsIFBoNWRJCdggUCwIeFlVFChQKAhYBHlUNGFkAE0VaVxAREAgSC1hXEREYH1kbX1tCBxpbHRlTXQoUCgIWAXBbAxZXBRgVEF4HGRZbGhlZWkwQChICHFlZEUBJUVkbX1tCBQ0UShVRXw5bHBUDDVRfDQZMVkBWU1kPVR0CShJRRAYcFwMEEFFFBhQASBQXXRYPHB1bSzwDdVNDTyVEVXMBIEBUUjNABBtaRkhXWkoFAlRFPyRFTgJyJjUTBwUcWVgHBhEHBBxRT0wWFgtJ X-ICL-Score: 2.33303322422 Authentication-Results: bimi.icloud.com; bimi=none X-ARC-Info: policy=fail; arc=none; r1=-20; r2=0 Authentication-Results: arc.icloud.com; arc=none Authentication-Results: dmarc.icloud.com; dmarc=pass header.from=jardineshasday.com X-DMARC-Policy: v=DMARC1; p=reject; pct=100 X-DMARC-Info: pass=pass; dmarc-policy=reject; s=r1; d=r1; pdomain=jardineshasday.com Authentication-Results: dkim-verifier.icloud.com; dkim=pass header.d=jardineshasday.com header.i=@jardineshasday.com header.b=q+vfqcQe Received-SPF: pass (spf.icloud.com: domain of jack.jr@jardineshasday.com designates 199.241.136.89 as permitted sender) receiver=spf.icloud.com; client-ip=199.241.136.89; helo=mail.estudios507.com; envelope-from=jack.jr@jardineshasday.com Authentication-Results: spf.icloud.com; spf=pass (spf.icloud.com: domain of jack.jr@jardineshasday.com designates 199.241.136.89 as permitted sender) smtp.mailfrom=jack.jr@jardineshasday.com Received: (Haraka outbound); Wed, 21 Jan 2026 19:15:36 +0000 Authentication-Results: mail.estudios507.com; auth=pass (plain) From: Jardines Hasday <jack.jr@jardineshasday.com> Content-Type: multipart/alternative; boundary="Apple-Mail=_B1D6017D-890E-40E0-A1CF-155CD24607C1" Mime-Version: 1.0 (Mac OS X Mail 16.0 \(3864.400.12\)) Subject: Test desde Jardines Hasday Message-Id: <D3C166C3-C7B5-4D84-8311-25460FB262DD@jardineshasday.com> Date: Wed, 21 Jan 2026 14:15:24 -0500 To: Jack Hasday <jackhasday@mac.com> X-Mailer: Apple Mail (2.3864.400.12) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=jardineshasday.com; s=cloudron-6667f4; h=from:subject:date:message-id:to:mime-version; bh=VqtpnOtGGQZjIGx33IRyZ889SaJP52QBrZ8qHxdfrqM=; b=q+vfqcQeonnBbDbB3JYYiX6ZHEDt36UK0bM+Nrh6ohSRynlyr6F7AHRdrD4XF173Sm1ys7/wGi oMIiO6vJaQUwC+H1wP/oMqohbM7Nkrs3je3G5E1IoGkVQV2QqwjYCMsh3rmR7Z7zgmz+RB2y/dhX vCwPVxMDamJtSXJiDI11k= X-Proofpoint-Spam-Details-Enc: AW1haW4tMjYwMTIxMDE2MSBTYWx0ZWRfXwrFyr1P6L/bI d/3yYo636bb7U/hxwbs9LQDvNpWvOcaoFmBAxvUW9eil0Riuy4bcDuQhLzZA+Lj6YSMIQ+YgekG 9VtZyHH3WP/BOtzTRpr8pTgsQ8OCP6t0Vj49ENLl6TZomxskE7EpjB5nVpxUOcRLNFdLgObSrFL p6fqEILdB+39T/tkkfnDN3ECUg889ACDqsfOB3yOz020C2cL4AfLz9WRtDX+QrjQCyaYoaoe+vA LX2Tq54mzkQgh+25F/NVhqKHivx8hsP+Ysz0o9wTMVaiVczmRXniPkeJZxqdBqpy+C6lVuzBtfr lavbCA3mCidpfbbiN0y X-Proofpoint-GUID: Mkyn_SIOD2w_wW6PNYAEEYT9qKP1vIEc X-Proofpoint-ORIG-GUID: Mkyn_SIOD2w_wW6PNYAEEYT9qKP1vIEc X-JNJ: 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 X-Authority-Info-Out: v=2.4 cv=SoudKfO0 c=1 sm=1 tr=0 ts=697125e3 cx=c_apl:c_apl_out:c_pps a=Ng/DTdlv9dYXrlarcUhKoA==:117 a=ry2iD/qIpUaetSALygwXCg==:17 a=vUbySO9Y5rIA:10 a=9QMxhTt3bwwA:10 a=VkNPw1HP01LnGYTKEx00:22 a=qTKaMy-KAAAA:8 a=zZ0dxMlp3nlOnM4htLIA:9 a=QEXdDO2ut3YA:10 a=e5bFYvIR1mMA:10 a=HsQN7Jx1AAAA:8 a=-toS3ZsGfbf9Qjwom14A:9 a=kb5bqZQ7yfcur1iC:21 a=_W_S_7VecoQA:10 a=lqcHg5cX4UMA:10 a=CjuIK1q_8ugA:10 a=KQqxNPgzF0kA:10 a=VEiTNn8F7TgA:10 a=ma5am7SHPxQHyC16eOKb:22 a=1EEwl0tWB0_S9o04m0hT:22 X-Proofpoint-Virus-Version: X-Proofpoint-Spam-Details: rule=notspam policy=default score=0 bulkscore=0 malwarescore=0 phishscore=0 spamscore=0 suspectscore=0 adultscore=0 mlxscore=0 clxscore=1030 mlxlogscore=414 classifier=spam authscore=0 adjust=0 reason=mlx scancount=1 engine=8.22.0-2510240001 definitions=main-2601210161 X-JNJ: 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 -
Hello @estudios507
Thank you for the detailed report. I will try to assist you to my best capabilities.
@estudios507 said in Cloudron rejects iCloud forwarding only when “Delete after forwarding” is enabled (SMTP 550 on MAIL FROM):
Identify which Cloudron restriction/policy is triggering “Mail from domain ‘X’ is not allowed from your host” in this scenario.
Regarding why this is happening.
When iCloud forwards messages in delete mode, iCloud uses the original sender’s MAIL FROM (envelope-from) unchanged instead of rewriting it. If that original sender domain is hosted on the same Cloudron server, Cloudron sees an external connection (from iCloud’s outbound IP) claiming to send mail from its own domain.
Cloudron treats that as spoofing and rejects it.
@estudios507 said in Cloudron rejects iCloud forwarding only when “Delete after forwarding” is enabled (SMTP 550 on MAIL FROM):
Confirm whether there is a supported and safe way in Cloudron to allow this specific flow (forwarding from iCloud with delete enabled) without broadly weakening anti-spoofing protections.
There is also another topic regarding this issue with iCloud, see: https://forum.cloudron.io/topic/1998/mail-error-after-sending-message-mail-from-domain-example-com-is-not-allowed-from-your-host
A fix is to add the iCloud servers to the domain A's SPF record.
Your current SPF record is:dig TXT estudios507.com +short "v=spf1 a:mail.estudios507.com include:_spf.safewebservices.com ~all"You can edit that to include apple:
"v=spf1 a:mail.estudios507.com include:_spf.safewebservices.com include:_spf.apple.com ~all"after that edit it can take some time to propagate, but this should resolve your issue.
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J james has marked this topic as solved
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