8000 [Mime] Line endings not correct when using S/MIME and Linux · Issue #36398 · symfony/symfony · GitHub
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[Mime] Line endings not correct when using S/MIME and Linux #36398

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TokkCorp opened this issue Apr 9, 2020 · 4 comments · Fixed by #36463
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[Mime] Line endings not correct when using S/MIME and Linux #36398

TokkCorp opened this issue Apr 9, 2020 · 4 comments · Fixed by #36463
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Bug Mime Status: Needs Review

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@TokkCorp
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TokkCorp commented Apr 9, 2020 •
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Symfony version(s) affected: 5.0+

Description
When sending mails using the symfony mailer the line endings in the message to the mailserver are missing the carriage return if S/MIME encryption is used on a linux server.

I've prepared four examples of what gets send to the mailserver:

Because of the wrong endings sending huge files leads to the following error:
PHP Fatal error: Uncaught Symfony\Component\Mailer\Exception\TransportException: Expected response code "250" but got code "501", with message "501 Syntax error - line too long". in /example/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php:298

How to reproduce
The Problem will occur always when sending an S/MIME encrypted Mail like this:

$email = (new Email())
    ->from('sender@example.com')
    ->to('recipient@example.com')
    ->subject('Encrypted mail with attachment')
    ->attachFromPath('./attachments/LoremIpsum.pdf')
    ->text(fopen('./attachments/content.txt', 'r'))
    ->html(fopen('./attachments/content.html', 'r'));

$encrypter = new SMimeEncrypter('./cert/smime.cer');
$encryptedEmail = $encrypter->encrypt($email);

The wrong line endings are also present without an attachment but the server error will occure only if the message is long enough to exceed the maximal line length.

Possible Solution
Fix the line endings in S/MIME encrypted messages.

Additional Information
It is working using Swiftmailer on the same systems so I would conclude the error is in the mailer component and not in openssl or any other system.
@TokkCorp TokkCorp added the Bug label Apr 9, 2020
@xabbuh xabbuh added the Mime label Apr 9, 2020
@nicolas-grekas
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/cc @sstok maybe?

@sstok
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sstok commented Apr 16, 2020

https://github.com/openssl/openssl/blob/6d9b4d7f4bf1ea9bc1d1b1bd8b7e83c6fbeed395/crypto/asn1/asn_mime.c#L244

if (flags & SMIME_CRLFEOL)
        mime_eol = "\r\n";
    else
        mime_eol = "\n";

But there is no way to use this constant directly in PHP (gotta love the OpenSSL extension).
I'm working on a pull request to normalize the line-ending to their correct format 👍

@sstok sstok mentioned this issue Apr 16, 2020
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@sstok
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sstok commented Apr 16, 2020

@TokkCorp can you try if #36463 fixes the problem?

@TokkCorp
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Just tried and can confirm that it is working with the change from this commit.

fabpot added a commit that referenced this issue Apr 17, 2020
@fabpot
bug #36463 [Mime] Ensure proper line-ending for SMIME (sstok)
6f81e03 
This PR was merged into the 5.0 branch.

Discussion
----------

[Mime] Ensure proper line-ending for SMIME

| Q             | A
| ------------- | ---
| Branch?       | 5.0
| Bug fix?      | yes
| New feature?  | no
| Deprecations? | no
| Tickets       | Fix #36398
| License       | MIT
| Doc PR        |

Commits
-------

5e3ccc2 [Mime] Ensure proper line-ending for SMIME
@fabpot fabpot closed this as completed Apr 17, 2020
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[Mime] Ensure proper line-ending for SMIME sstok/symfony
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@fabpot @nicolas-grekas @sstok @xabbuh @TokkCorp @carsonbot
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