cannot parse header or From address when replying to a mail #344

wneessen · 2025-04-28T19:57:24Z

A customer tried to reply to a mail today and the delivery was rejected with an error during parsing message for smtputf8 check. The error was: parsing message From address - parsing message: reading header line: line too long

His from address is pretty short, any idea what happend here?

Full log is here (sensitive date redacted):

Apr 28 17:10:15 mail1 mox[5029]: l=info m="new connection" pkg=smtpserver remote=XXX.XXX.XXX.XXX:62607 local=YYY.YYY.YYY.YYY:587 submission=true tls=false viahttps=false listener=public cid=19658108294 delta="77.784µs"
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=ehlo code=250 ecode= duration="54.596µs" cid=19658108294 delta=33.309474ms
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=starttls code=220 ecode=2.0.0 duration="36.196µs" cid=19658108294 delta=19.647185ms
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="starting tls server handshake" pkg=smtpserver cid=19658108294 delta="167.394µs"
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="tls handshake completed" pkg=smtpserver version=tls1.2 ciphersuite=tls_ecdhe_ecdsa_with_aes_128_gcm_sha256 sni=mox.server.tld resumed=false clientcerts=0 cid=19658108294 delta=43.691806ms
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=ehlo code=250 ecode= duration="35.306µs" cid=19658108294 delta=50.73576ms
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=auth code=235 ecode=2.7.0 duration=37.740069ms cid=19658108294 delta=57.159882ms username=user@on.mox.server.tld
Apr 28 17:10:15 mail1 mox[5029]: l=info m="login attempt" pkg=smtpserver address=user@on.mox.server.tld account=user@on.mox.server.tld protocol=submission authmech= result=ok remoteip=XXX.XXX.XXX.XXX localip=YYY.YYY.YYY.YYY tls="version=tls1.2 ciphersuite=tls_ecdhe_ecdsa_with_aes_128_gcm_sha256 sni=mox.server.tld resumed=false alpn=" useragent= tlspubkeyfp= count=3 cid=19658108294 username=user@on.mox.server.tld
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=mail code=250 ecode=2.1.0 duration="37.598µs" cid=19658108294 delta=51.38535ms username=user@on.mox.server.tld
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=rcpt code=250 ecode=2.1.0 duration="32.159µs" cid=19658108294 delta=19.049541ms username=user@on.mox.server.tld
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="parsing message for smtputf8 check" err="reading header line: line too long" pkg=smtpserver cid=19658108294 delta=79.872547ms username=user@on.mox.server.tld
Apr 28 17:10:15 mail1 mox[5029]: l=info m="parsing message From address" err="parsing message: reading header line: line too long" pkg=smtpserver user=user@on.mox.server.tld cid=19658108294 delta="191.783µs" username=user@on.mox.server.tld
Apr 28 17:10:15 mail1 mox[5029]: l=debug m="smtp command result" err="cannot parse header or From address: parsing message: reading header line: line too long" pkg=smtpserver kind=submission cmd=data code=550 ecode=5.6.0 duration=60.580296ms cid=19658108294 delta="342.3µs" username=user@on.mox.server.tld
Apr 28 17:10:18 mail1 mox[5029]: l=debug m="smtp command result" pkg=smtpserver kind=submission cmd=quit code=221 ecode=2.0.0 duration="18.523µs" cid=19658108294 delta=2.685673085s username=user@on.mox.server.tld
Apr 28 17:10:18 mail1 mox[5029]: l=info m="connection closed" pkg=smtpserver cid=19658108294 delta="218.604µs" username=user@on.mox.server.tld

The text was updated successfully, but these errors were encountered:

mjl- · 2025-04-28T22:00:32Z

I don't think the problem is with the From address or header. The error message is just saying it was looking for the From address, and was parsing the message, and then encountered a long header when parsing the message. Any header that is longer than 1000 characters would trigger this.

I don't suppose you have the message, or just its headers, to see what's going on with them?

I check my logging, found a few lines about long header lines. They were spams with an actual too long header (looked like a corrupt dkim header).

Btw, am I understanding it correctly this is during submission (to the queue for outgoing delivery), not for incoming deliveries? If it is during submission, and the headers are indeed too long, we can look at the application and why it generates long headers.

wneessen · 2025-04-29T07:39:08Z

I don't suppose you have the message, or just its headers, to see what's going on with them?

I asked the client for the headers of the original mail and I think it's the References header, which is 1000+ chars long.

Received: from
        eur05-db8-obe.outbound.protection.outlook.com (mail-db8eur05on2125.outbound.protection.outlook.com [40.107.20.125])
        by mox.server.tld ([YYY.YYY.YYY.YYY]) via tcp with ESMTPS id
        j1LhcxAzcCODWET47cvF1w (TLS1.3 TLS_AES_128_GCM_SHA256) for
        user@domain.on.mox.server.tld; 23 Apr 2025 14:00:18 +0200
Received: from AM0PR01MB6515.eurprd01.prod.exchangelabs.com
	2603:10a6:20b:161::13) by AS1PR01MB9011.eurprd01.prod.exchangelabs.com
	2603:10a6:20b:4dc::12) with Microsoft SMTP Server (version=TLS1_2,
	ipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.8655.35; Wed, 23 Apr
	025 12:00:12 +0000
Received: from AM0PR01MB6515.eurprd01.prod.exchangelabs.com
	[fe80::fd51:330c:3070:8e6a]) by AM0PR01MB6515.eurprd01.prod.exchangelabs.com
	[fe80::fd51:330c:3070:8e6a%4]) with mapi id 15.20.8678.021; Wed, 23 Apr 2025
	2:00:12 +0000
From: Info@sender.domain.tld
To: user@domain.on.mox.server.tld
References: AM8PR01MB76841E7AC0D81DD8A1B5C55184DE2@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM8PR01MB76840E4964043D81066B0E3684DE2@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM8PR01MB76843E475B69F8167E9F4D5E84DE AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM8PR01MB7684CB8CDCC31EF096C8999584DE2@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM8PR01MB768497F86FF53BF7EECFEFFF84DE2@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM8PR01MB76841D66C71F4AEAD5EA7C0E84DE2@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM8PR01MB7684A9CB2AB131EC97E44EA184AA2@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM0PR01MB6515511799A707F334095076EA602@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB65150EEFC9A604F37C41B5CAEA602@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB6515D77ABFD69522C50BF86EEA632@AM0PR01MB6515.eurprd01.prod.exchangelabs.com DBBPR01MB7692AB5E6999049F34C207B184582@DBBPR01MB7692.eurprd01.prod.exchangelabs.com <AM8PR01MB76846D32184683482BC882A684E92@AM8PR01MB7684.eurprd01.prod.exchangelabs.com> AM8PR01MB7684261298D18325CA9E9F3F84F42@AM8PR01MB7684.eurprd01.prod.exchangelabs.com AM0PR01MB65151062740C2618B61CFDF4EAA72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB6515AA210788296A629ADFF9EAA72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB6515039939088DD8FE8462B3EAA62@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB651538834C1CEC6C10504D7AEAA62@AM0PR01MB6515.eurprd01.prod.exchangelabs.com DB8PR01MB65208CCFE83D679A2E8EEE0EEAA12@DB8PR01MB6520.eurprd01.prod.exchangelabs.com DB8PR01MB65206A6671E436990D196C6EEAA12@DB8PR01MB6520.eurprd01.prod.exchangelabs.com AM0PR01MB6515DF0DE579D2F74E06951AEAAA2@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB6515E4F6FD2B4F8A9D9A0195EAB72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB6515F99A0648C175DC6A5945EAB72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com AM0PR01MB651561674AAFD4A6A76BAC61EAB72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com <AM0PR01MB6515CF7808B896A2BD06AF33EAB72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com>
In-Reply-To: AM0PR01MB6515CF7808B896A2BD06AF33EAB72@AM0PR01MB6515.eurprd01.prod.exchangelabs.com
Subject: Initiativbewerbung  - Rechtsanwaltsfachangestellte
Date: Wed, 23 Apr 2025 14:00:12 +0200
Message-ID: AM0PR01MB65151EE403B40C8340D894FDEABA2@AM0PR01MB6515.eurprd01.prod.exchangelabs.com
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Btw, am I understanding it correctly this is during submission (to the queue for outgoing delivery), not for incoming deliveries? If it is during submission, and the headers are indeed too long, we can look at the application and why it generates long headers.

Correkt, the client received a mail and tried to reply to it and mox rejected it with the error message in my initial post.

Looks like a typical "MS doesn't care for RFCs and standards" thing.

mjl- · 2025-04-29T11:07:19Z

Yeah, that's the header causing trouble. Outlook should just wrap it over multiple lines. Mox rejects it during submission in part because we don't want to be a bad sender, and we need to protect our reputation: Anything that is invalid about email messages can be held against your mail server or sending domain by receiving mail servers as a sign of spam.

A workaround is probably to send a new message, not reply to the existing message.

If they are a customer of microsoft, they could file a bug report with them (I don't think that's possible if you're not a paying microsoft customer).

Perhaps we should stretch our limits a bit more. I think we already have a way to parse messages less strictly, allowing longer header lines (but there will always be some limit).

wneessen · 2025-04-29T13:14:29Z

A workaround is probably to send a new message, not reply to the existing message.

Yeah, I suggested that too. I haven't heard back but it probably worked.

If they are a customer of microsoft, they could file a bug report with them (I don't think that's possible if you're not a paying microsoft customer).

I don't think they are.

Perhaps we should stretch our limits a bit more. I think we already have a way to parse messages less strictly, allowing longer header lines (but there will always be some limit).

Maybe for headers that are known to hold longer values that might be a good idea. It's the first time i'm seeing this so it's likely a fluke more than a general issue. I think for now we can close this issue as the question on "why" has been answered.

wneessen closed this as completed Apr 29, 2025

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cannot parse header or From address when replying to a mail #344

cannot parse header or From address when replying to a mail #344

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cannot parse header or From address when replying to a mail #344

cannot parse header or From address when replying to a mail #344

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