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feat: Upload whole certificate chain when uploading a certificate for…
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… S/MIME in pkcs12 format. Include whole certificate chain in signed messages. Use whole certificate chain to verify certificates.

Fixes #9190

Signed-off-by: Patrick Bender <[email protected]>
Signed-off-by: Richard Steinmetz <[email protected]>
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@IchbinkeinReh @st3iny
IchbinkeinReh authored and st3iny committed May 28, 2024
1 parent 3351645 commit bcc2530
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Showing 8 changed files with 291 additions and 4 deletions.
10 changes: 8 additions & 2 deletions lib/Service/SmimeService.php
View file
Original file line number Diff line number Diff line change
Expand Up @@ -182,13 +182,16 @@ public function parseCertificate(string $certificate): SmimeCertificateInfo {
}
}

$decryptedCertificateFile = $this->tempManager->getTemporaryFile();
file_put_contents($decryptedCertificateFile, $certificate);

$caBundle = [$this->certificateManager->getAbsoluteBundlePath()];
return new SmimeCertificateInfo(
$certificateData['subject']['CN'] ?? null,
$certificateData['subject']['emailAddress'] ?? $certificateData['subject']['CN'],
$certificateData['validTo_time_t'],
$purposes,
openssl_x509_checkpurpose($certificate, X509_PURPOSE_ANY, $caBundle) === true,
openssl_x509_checkpurpose($certificate, X509_PURPOSE_ANY, $caBundle, $decryptedCertificateFile) === true,
);
}

Expand Down Expand Up @@ -376,13 +379,16 @@ public function signMimePart(Horde_Mime_Part $part,
);
}

$decryptedCertificateFile = $this->tempManager->getTemporaryFile();
file_put_contents($decryptedCertificateFile, $decryptedCertificate);

$inPath = $this->tempManager->getTemporaryFile();
$outPath = $this->tempManager->getTemporaryFile();
file_put_contents($inPath, $part->toString([
'canonical' => true,
'headers' => true,
]));
if (!openssl_pkcs7_sign($inPath, $outPath, $decryptedCertificate, $decryptedKey, null)) {
if (!openssl_pkcs7_sign($inPath, $outPath, $decryptedCertificate, $decryptedKey, null, PKCS7_DETACHED, $decryptedCertificateFile)) {
throw new SmimeSignException('Failed to sign MIME part');
}

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61 changes: 61 additions & 0 deletions src/tests/data/[email protected]
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Original file line number Diff line number Diff line change
@@ -0,0 +1,61 @@
-----BEGIN CERTIFICATE-----
MIIFUjCCAzqgAwIBAgIQPNReuUyM+DUIY0jIs9wXfjANBgkqhkiG9w0BAQsFADAU
MRIwEAYDVQQDDAlTL01JTUUgQ0EwHhcNMjMwMTI2MTAxMjIzWhcNMjQwMTI2MTAx
MjIzWjAzMQ0wCwYDVQQDDAR1c2VyMSIwIAYJKoZIhvcNAQkBFhN1c2VyQGltYXAu
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aYAHcRXlsEqTNzseEXHIYWHosJLHRQ==
-----END CERTIFICATE-----

-----BEGIN CERTIFICATE-----
MIIFCTCCAvGgAwIBAgIUIPN87gXhW2+tZ34jbBb/GY/C9yMwDQYJKoZIhvcNAQEL
BQAwFDESMBAGA1UEAwwJUy9NSU1FIENBMB4XDTIzMDEyNjA5NDMwNVoXDTMzMDEy
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4LC3+GEsTFdDgpSOJ6sUj7f6kQkXjOAHhngReX8Zv+l9pnENtdZiKJCz4Vl4
-----END CERTIFICATE-----
2 changes: 1 addition & 1 deletion src/tests/unit/util/pkcs12.spec.js
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Original file line number Diff line number Diff line change
Expand Up @@ -36,7 +36,7 @@ describe('pkcs12', () => {
})

it('correctly handles PKCS#12 files with multiple cert bags', () => {
const certPem = readTestData('[email protected]').replaceAll('\n', '\r\n')
const certPem = readTestData('[email protected].chain.crt').replaceAll('\n', '\r\n')
const keyPem = readTestData('[email protected]').replaceAll('\n', '\r\n')
const pkcs12Der = toArrayBuffer(readTestDataRaw('[email protected]'))

Expand Down
2 changes: 1 addition & 1 deletion src/util/pkcs12.js
View file
Original file line number Diff line number Diff line change
Expand Up @@ -51,7 +51,7 @@ export function convertPkcs12ToPem(pkcs12Der, password) {
}

return {
certificate: forge.pki.certificateToPem(certBags[0].cert),
certificate: certBags.map((certBag) => forge.pki.certificateToPem(certBag.cert)).join('\r\n'),
privateKey: forge.pki.privateKeyToPem(keyBags[0].key),
}
}
Expand Down
34 changes: 34 additions & 0 deletions tests/Unit/Service/SmimeServiceTest.php
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Original file line number Diff line number Diff line change
Expand Up @@ -423,6 +423,36 @@ public function provideParseCertificateData(): array {
false,
),
],
[ // Full chain: Leaf -> Intermediate CA -> CA
$this->getTestCertificate('[email protected]'),
new SmimeCertificateInfo(
'chain',
'[email protected]',
4870519697,
new SmimeCertificatePurposes(true, true),
true,
),
],
[ // Partial chain: Leaf -> Intermediate CA
$this->getTestCertificate('[email protected]'),
new SmimeCertificateInfo(
'chain',
'[email protected]',
4870519697,
new SmimeCertificatePurposes(true, true),
true,
),
],
[ // Leaf only
$this->getTestCertificate('[email protected]'),
new SmimeCertificateInfo(
'chain',
'[email protected]',
4870519697,
new SmimeCertificatePurposes(true, true),
false,
),
],
];
}

Expand All @@ -435,6 +465,10 @@ public function testParseCertificate(SmimeCertificate $certificate,
->method('getAbsoluteBundlePath')
->willReturn(__DIR__ . '/../../data/smime-certs/imap.localhost.ca.crt');

$this->tempManager->expects(self::once())
->method('getTemporaryFile')
->willReturnCallback(fn () => $this->createTempFile());

$this->assertEquals(
$expected,
$this->smimeService->parseCertificate($certificate->getCertificate()),
Expand Down
32 changes: 32 additions & 0 deletions tests/data/smime-certs/[email protected]
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Original file line number Diff line number Diff line change
@@ -0,0 +1,32 @@
-----BEGIN CERTIFICATE-----
MIIFdDCCA1ygAwIBAgIRAJp/VZ0n301xLR86gjdy8BswDQYJKoZIhvcNAQELBQAw
MDEuMCwGA1UEAwwlaW1hcC5sb2NhbGhvc3QgUy9NSU1FIEludGVybWVkaWF0ZSBD
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LKrGUdB8XKI=
-----END CERTIFICATE-----
62 changes: 62 additions & 0 deletions tests/data/smime-certs/[email protected]
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Original file line number Diff line number Diff line change
@@ -0,0 +1,62 @@
-----BEGIN CERTIFICATE-----
MIIFdDCCA1ygAwIBAgIRAJp/VZ0n301xLR86gjdy8BswDQYJKoZIhvcNAQELBQAw
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LKrGUdB8XKI=
-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----
MIIFMjCCAxqgAwIBAgIQRknyt1KzW/+fU1oN1f82RjANBgkqhkiG9w0BAQsFADAj
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92 changes: 92 additions & 0 deletions tests/data/smime-certs/[email protected]
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