I first posted this to spf-discuss, but folk there said that Microsoft do not reject based on SPF issues, and that it was more suitable for this list. Apologies if there is etiquette I breach.

We send out quite large amounts of mail from groups.ilovefreegle.org. A small proportion of them get bounced back by Hotmail.

So far as I can tell from the NDR (source below, but with the recipient email masked to xxxxx, and with the large content trimmed) what is happening is: We mail a hotmail user. The Hotmail user is set up to forward. I'm guessing that from headers like this:
Resent-From: <x <mailto:s.bon...@hotmail.com>xxxx>
X-MS-Exchange-Inbox-Rules-Loop: x <mailto:s.bon...@hotmail.com>xxxx
The message is then sent from one of Microsoft's servers to another, as per this header:
Received: from EUR02-AM5-obe.outbound.protection.outlook.com ([40.92.67.40]) by COL004-MC5F27.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23143);
That server then fails SPF and non-delivers because the SPF records for my domain don't list Hotmail's server 40.92.67.40. Obviously. However it's quite possible that I've mis-read this, or am doing something else wrong. I've had a suggestion that I should add a sender-id record of "spf2.0/pra ?all", but I'm not familiar with sender-id.

I've had no luck getting the attention of anyone at Microsoft at a suitable level. Any help welcome.

Edward


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Date: Sun, 26 Mar 2017 17:27:01 -0700
From: st...@hotmail.com
Subject: [Eastbourne Freegle] What's New (22 messages) - Mobile Phone, metal
detector, single duvet, tiles, Plastic straws...
To: ge...@ilovefreegle.org
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--B5BA3D3E-6C6A-42C6-A416-C5FAE338BD42
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This is an email abuse report for an email message received from IP 40.92.67.40 on Sun, 26 Mar 2017 17:27:00 -0700. The message below did not meet the sending domain's authentication policy. For more information about this format please see http://www.ietf.org/rfc/rfc5965.txt.

--B5BA3D3E-6C6A-42C6-A416-C5FAE338BD42
Content-Type: message/feedback-report

Feedback-Type: auth-failure
User-Agent: XMR/2.2
Version: 1.0
Original-Mail-From: <eastbournefreegle-a...@groups.ilovefreegle.org>
Arrival-Date: Sun, 26 Mar 2017 17:27:00 -0700
Message-ID: <69c98f5352c5af2e73169bc8bea6a...@users.ilovefreegle.org>
Authentication-Results: hotmail.com; spf=fail (sender IP is 40.92.67.40; identity alignment result is pass and alignment mode is relaxed) smtp.mailfrom=eastbournefreegle-a...@groups.ilovefreegle.org; dkim=permerror (identity alignment result is pass and alignment mode is relaxed) header.d=groups.ilovefreegle.org; x-hmca=fail header.id=eastbournefreegle-a...@groups.ilovefreegle.org
Source-IP: 40.92.67.40
Auth-Failure: spf
Reported-Domain: groups.ilovefreegle.org
DKIM-Domain: groups.ilovefreegle.org
DKIM-Identity: @groups.ilovefreegle.org
DKIM-Selector: x


--B5BA3D3E-6C6A-42C6-A416-C5FAE338BD42
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Authentication-Results: hotmail.com; spf=fail (sender IP is 40.92.67.40; identity alignment result is pass and alignment mode is relaxed) smtp.mailfrom=eastbournefreegle-a...@groups.ilovefreegle.org; dkim=permerror (identity alignment result is pass and alignment mode is relaxed) header.d=groups.ilovefreegle.org; x-hmca=fail header.id=eastbournefreegle-a...@groups.ilovefreegle.org
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From: Eastbourne Freegle <eastbournefreegle-a...@groups.ilovefreegle.org>
To: "REDACTED" <postmas...@outlook.com>
Subject: [Eastbourne Freegle] What's New (22 messages) - Mobile Phone, metal
detector, single duvet, tiles, Plastic straws...
Thread-Topic: [Eastbourne Freegle] What's New (22 messages) - Mobile Phone,
metal detector, single duvet, tiles, Plastic straws...
Thread-Index: AQHSppDYm1pV6pQ93Uq46X2he1PFEQ==
Date: Mon, 27 Mar 2017 00:26:53 +0000
Message-ID: <69c98f5352c5af2e73169bc8bea6a...@users.ilovefreegle.org>
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