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Avoid double encrypting PGP parts encoded as plain text (fixes #1083)
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@mdecimus
mdecimus committed Jan 11, 2025
1 parent 5af0fb4 commit 013c580
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Showing 3 changed files with 156 additions and 16 deletions.
36 changes: 33 additions & 3 deletions crates/jmap/src/email/crypto.rs
View file
Original file line number Diff line number Diff line change
Expand Up @@ -17,7 +17,7 @@ use common::{auth::AccessToken, Server};
use directory::backend::internal::manage;
use jmap_proto::types::{collection::Collection, property::Property};
use mail_builder::{encoders::base64::base64_encode_mime, mime::make_boundary};
use mail_parser::{decoders::base64::base64_decode, Message, MessageParser, MimeHeaders};
use mail_parser::{decoders::base64::base64_decode, Message, MessageParser, MimeHeaders, PartType};
use openpgp::{
parse::Parse,
serialize::stream,
Expand Down Expand Up @@ -372,7 +372,7 @@ impl EncryptMessage for Message<'_> {
}

fn is_encrypted(&self) -> bool {
self.content_type().is_some_and(|ct| {
if self.content_type().is_some_and(|ct| {
let main_type = ct.c_type.as_ref();
let sub_type = ct
.c_subtype
Expand All @@ -390,7 +390,37 @@ impl EncryptMessage for Message<'_> {
}))))
|| (main_type.eq_ignore_ascii_case("multipart")
&& sub_type.eq_ignore_ascii_case("encrypted"))
})
}) {
return true;
}

if self.parts.len() <= 2 {
let mut text_part = None;
let mut is_multipart = false;

for part in &self.parts {
match &part.body {
PartType::Text(text) => {
text_part = Some(text.as_ref());
}
PartType::Multipart(_) => {
is_multipart = true;
}
_ => (),
}
}

match text_part {
Some(text) if self.parts.len() == 1 || is_multipart => {
if text.trim_start().starts_with("-----BEGIN PGP MESSAGE-----") {
return true;
}
}
_ => (),
}
}

false
}
}

Expand Down
134 changes: 122 additions & 12 deletions tests/resources/crypto/is_encrypted.txt
View file
Original file line number Diff line number Diff line change
Expand Up @@ -4,14 +4,14 @@ Content-Type: multipart/encrypted;
boundary="17778885806d6b28_46555a54adda6fa5_d83705f326a6b951"

body
---
!!!
Subject: FALSE
Content-Type: multipart/signed;
protocol="application/pkcs7-signature";
boundary="17778885806d6b28_46555a54adda6fa5_d83705f326a6b951"

body
---
!!!
Subject: TRUE
Content-Type: application/pkcs7-mime;
name="smime.p7m";
Expand All @@ -21,7 +21,7 @@ Content-Disposition: attachment;
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/pkcs7-signature;
name="smime.p7s"; smime-type="signed-data"
Expand All @@ -30,7 +30,7 @@ Content-Disposition: attachment;
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/octet-stream;
name="smime.p7m"
Expand All @@ -39,63 +39,173 @@ Content-Disposition: attachment;
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/octet-stream;
name="smime.p7m"
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/octet-stream
Content-Disposition: attachment;
filename="smime.p7m"
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/octet-stream
Content-Disposition: attachment;
filename="smime.p7s"
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/octet-stream
Content-Disposition: attachment;
filename="smime.p7c"
Content-Transfer-Encoding: base64

body
---
!!!
Subject: TRUE
Content-Type: application/octet-stream
Content-Disposition: attachment;
filename="smime.p7z"
Content-Transfer-Encoding: base64

body
---
!!!
Subject: FALSE
Content-Type: application/octet-stream
Content-Disposition: attachment;
filename="file.gz"
Content-Transfer-Encoding: base64

body
---
!!!
Subject: FALSE
Content-Type: application/octet-stream
Content-Disposition: attachment
Content-Transfer-Encoding: base64

body
---
!!!
Subject: FALSE
Content-Type: multipart/mixed;
boundary="17778885806d6b28_46555a54adda6fa5_d83705f326a6b951"

body
!!!
Subject: TRUE
Content-Type: multipart/mixed; boundary="----sinikael-?=_1-17364333937490.28304631087789"

------sinikael-?=_1-17364333937490.28304631087789
Content-Type: text/plain
Content-Transfer-Encoding: quoted-printable


-----BEGIN PGP MESSAGE-----
Version: Mailvelope v6.0.1
Comment: https://mailvelope.com

wcFMAy3n9oegk2NSARAApgl4nuztm5uxuCe+7ISW9Ox+315/pCHZmOUibORX
xGEbUs+ZgTqKIdYMet3+zSS70ykgjZDvh+cLm1oGmD5ZzLxSMjhgLpqrA0tG
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=3DaQyM
-----END PGP MESSAGE-----

------sinikael-?=_1-17364333937490.28304631087789--
!!!
Subject: TRUE
Content-Type: text/plain
Content-Transfer-Encoding: quoted-printable



-----BEGIN PGP MESSAGE-----
Version: Mailvelope v6.0.1
Comment: https://mailvelope.com

wcFMAy3n9oegk2NSARAApgl4nuztm5uxuCe+7ISW9Ox+315/pCHZmOUibORX
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=3DaQyM
-----END PGP MESSAGE-----
2 changes: 1 addition & 1 deletion tests/src/jmap/crypto.rs
View file
Original file line number Diff line number Diff line change
Expand Up @@ -241,7 +241,7 @@ pub fn check_is_encrypted() {
)
.unwrap();

for raw_message in messages.split("---") {
for raw_message in messages.split("!!!") {
let is_encrypted = raw_message.contains("TRUE");
let message = MessageParser::new()
.parse(raw_message.trim().as_bytes())
Expand Down

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