K-9: 'From' header is missing.

[JakeQZ]

Expected behavior

Email should be sent to GMail and Yahoo account holders.

Actual behavior

GMail and Yahoo reject emails with the following errors:

GMail:
Reason: There was an error while attempting to deliver your message with [Subject: ""] to @gmail.com. MTA * received this response from the destination host IP - 209.85.145.27 - 550 , 550-5.7.1 [188.121.53.111] Our system has detected that this message is
550-5.7.1 not RFC 5322 compliant:
550-5.7.1 'From' header is missing.
550-5.7.1 To reduce the amount of spam sent to Gmail, this message has been
550-5.7.1 blocked. Please visit
550-5.7.1 https://support.google.com/mail/?p=RfcMessageNonCompliant
550 5.7.1 and review RFC 5322 specifications for more information. a75-v6si5640959ioa.39 - gsmtp

Yahoo:
Reason: There was an error while attempting to deliver your message with [Subject: ""] to @yahoo.co.uk. MTA * received this response from the destination host IP - 212.82.101.46 - 554 , 554 Message not allowed - [299]
.

Note that other mail servers accepted and delivered the message.

Steps to reproduce

1. Install and set-up K-9;
2. Reply-All to an email with about 30 recipients, some with a Yahoo or GMail address;
3. Check Inbox for 'Message Delivery Failure' responses.

Environment

K-9 Mail version:
5.403

Android version:
4.1.2
(Samsung GT-I8160)

Account type (IMAP, POP3, WebDAV/Exchange):
POP3

[JakeQZ]

Closer inspection of the rejected message shows the problem is probably with the To: line preceding From:. With about 30 recipients, it wraps to the next line at just shy of 1,000 characters, but without a space or tab as the first character on the new line. It seems that this throws Yahoo and GMail's parsers so they don't pick up the From: line at all.

To: Some Body <[email protected]>,...,Somebody Else
<[email protected]>,...,A N Other <[email protected]>
From: Bug Reporter <[email protected]>

Should be

To: Some Body <[email protected]>,...,Somebody Else
 <[email protected]>,...,A N Other <[email protected]>
From: Bug Reporter <[email protected]>

Note the space where the To: field continues to the next line.

Please see https://tools.ietf.org/html/rfc5322#section-2.2.3:

Long Header Fields

Each header field is logically a single line of characters comprising
the field name, the colon, and the field body. For convenience
however, and to deal with the 998/78 character limitations per line,
the field body portion of a header field can be split into a
multiple-line representation; this is called "folding". The general
rule is that wherever this specification allows for folding white
space (not simply WSP characters), a CRLF may be inserted before any
WSP.

The CRLF may be inserted _before_, not _instead of_ the WSP.

[dmth]

@JakeQZ Thank you for your thorough report.
I also experienced the "'From' header is missing" Message from GMail and Yahoo when replying to threads with > 29 To addresses.

Nevertheless, I cannot support your linebreak-idea from https://github.com/k9mail/k-9/issues/3544#issuecomment-410562270 as other raw-viewers (such as Thunderbird do not show a broken list of To addresses.

In addition, in my "broken" E-Mail the From header precedes the To header

Date: Tue, 07 Aug 2018 15:24:14 +0200
From: Bug Reporter <[email protected]>
To: Some Body <[email protected]>,...,Somebody Else <[email protected]>,...,A N Other <[email protected]>
Subject: A Subject
User-Agent: K-9 Mail for Android

[JakeQZ]

Nevertheless, I cannot support your linebreak-idea from #3544 (comment) as other raw-viewers (such as Thunderbird do not show a broken list of To addresses.

If I open the rejected message in Thunderbird, the list of To addresses is truncated at the one which wraps to the next line, which shows with an empty email address.

[eolith]

Also encountering this issue on a family even planning set of emails. All yahoo and gmail addresses bounceback, which is a lot of them. Had this for a couple months, and just decided to address it today after another one. Please resolve, as I have to use another app. I've used K9 mail for a long time, but this is worth switching over.

[cketti]

Duplicate of #822.

[stephanroch]

Please consider to reopen and fix this bug. #822 is still open (and not scheduled for immediate resolution?), but only #3554 has an example and a good analysis. The folding of long header fields breaks RFC-5332 2.2.3. The CRLF may be inserted before, not instead of the WSP.

[xvanausloos]

Hello,

I have same issue using K9 email client in Android. (latest version)
Is a fix available?

Thank you

[Fjorstut]

As above, please consider to fix this issue. I receive 'undeliverable mail' (*) bounce back messages when trying to sent to many recipients. I receive bounce back messages from only gmail and yahoo recipients.

*yahoo says: 554 Message not allowed - [299]
*gmail says: 550 5.7.1 [ip] Our system has detected that this message is not RFC 5322 compliant: 'From' header is missing.

[JakeQZ]

It looks like this has been fixed in the code base (#3912, 14 Feb) but not yet included in a release (latest release 2 Sep 2018).

Please could we have a new release which includes this fix (https://github.com/k9mail/k-9/pull/3912#issuecomment-521985166)?

[siccovansas]

@JakeQZ I'm not involved in K-9, but you can track the progress to the new 5.800 version here: https://github.com/k9mail/k-9/milestone/24

I agree that it has been quite a while since the last release, but I am really pleased to see that K-9 is being actively developed :)!