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* [PATCH proxmox v2] sendmail: conform more to mime Content-Disposition header and wrap lines
@ 2026-02-19 14:58 Shannon Sterz
  0 siblings, 0 replies; only message in thread
From: Shannon Sterz @ 2026-02-19 14:58 UTC (permalink / raw)
  To: pbs-devel

the http and mime Content-Disposition headers function slightly
differently. for the http version the following would be valid
according to rfc 6266 [1]:

Content-Disposition: attachment; filename="file.pdf";
    filename*=UTF-8''file.pdf

specifying multiple filename attributes like this isn't valid for mime
messages. according to rfc 2183 [2] the above should be expressed like
so for mime messages (one variant, multiple are supported):

Content-Disposition: attachment;
    filename*0*=UTF-8''file.bin

while rfc 2183 [2] would in theory allow for multiple filename
parameters similar to rfc 6266, in practice MIME::Tools [2] considers
this as ambigous content [3]. in more recent versions of Proxmox Mail
Gateway, such messages are rejected [4].

this patch implements proper filename handling and also wraps
filenames in the content disposition and content type headers
appropriatelly to a mail being rejected due to having mime headers
that are too long as described in rfcs 2231 [5] and 2045 [6].

[1]: https://datatracker.ietf.org/doc/html/rfc6266/
[2]: https://datatracker.ietf.org/doc/html/rfc2183#section-2
[3]: https://metacpan.org/pod/MIME::Head#ambiguous_content
[4]:
https://git.proxmox.com/?p=pmg-api.git;a=commitdiff;h=66f51c62f789b4c20308b7594fbbb357721b0844
[5]: https://datatracker.ietf.org/doc/html/rfc2231#section-7
[6]: https://datatracker.ietf.org/doc/html/rfc2045/#section-6.8

Signed-off-by: Shannon Sterz <s.sterz@proxmox.com>
---

tested this with peat on the following muas:

* aerc
* thunderbird
* ios mail app
* canary mail app
* start mail web client
* gmail web client
* outlook web client

noticed this when peat suddenly struggled to send mails. thanks @ Stoiko
Ivanov for helping with analysing this issue.

Changelog:
---------

* wrap lines more correctly ensuring that encoded lines don't exceed 76
  chars (thanks @ Stoiko Ivanov)
* refactored the wrapping logic to be more general

 proxmox-sendmail/src/lib.rs | 167 ++++++++++++++++++++++++++++--------
 1 file changed, 129 insertions(+), 38 deletions(-)

diff --git a/proxmox-sendmail/src/lib.rs b/proxmox-sendmail/src/lib.rs
index f5b04afd..ec8488a4 100644
--- a/proxmox-sendmail/src/lib.rs
+++ b/proxmox-sendmail/src/lib.rs
@@ -44,23 +44,83 @@ const RFC5987SET: &AsciiSet = &CONTROLS
 /// base64 encode and hard-wrap the base64 encoded string every 72 characters. this improves
 /// compatibility.
 fn encode_base64_formatted<T: AsRef<[u8]>>(raw: T) -> String {
-    const TEXT_WIDTH: usize = 72;
-
     let encoded = proxmox_base64::encode(raw);
-    let bytes = encoded.as_bytes();

-    let lines = bytes.len().div_ceil(TEXT_WIDTH);
-    let mut out = Vec::with_capacity(bytes.len() + lines - 1); // account for 1 newline per line
+    format_text(&encoded, |_| "".into(), "", 0, true)
+}

-    for (line, chunk) in bytes.chunks(TEXT_WIDTH).enumerate() {
+fn encode_filename_formatted(filename: &str) -> String {
+    let encoded = format!("UTF-8''{}", utf8_percent_encode(filename, RFC5987SET));
+
+    let format_prefix = |l| {
+        if let Some(l) = l {
+            format!("\tfilename*{l}*=")
+        } else {
+            "\tfilename*NN*=".into()
+        }
+    };
+
+    format_text(&encoded, format_prefix, ";", 0, true)
+}
+
+fn format_text<F>(
+    text: &str,
+    prefix: F,
+    suffix: &str,
+    shorten_first: usize,
+    skip_last_suffix: bool,
+) -> String
+where
+    F: Fn(Option<usize>) -> String,
+{
+    const DEFAULT_TEXT_WIDTH: usize = 72;
+
+    let bytes = text.as_bytes();
+    let suffix = suffix.as_bytes();
+
+    let format_text_len = suffix.len() + prefix(None).len();
+    let lines = (bytes.len() + shorten_first).div_ceil(DEFAULT_TEXT_WIDTH - format_text_len);
+
+    // bytes + formatting and "\n" per line - no "\n" in the last line
+    let mut capacity = bytes.len() + (format_text_len + 1) * lines - 1;
+
+    if skip_last_suffix {
+        capacity -= suffix.len();
+    }
+
+    let mut out = Vec::with_capacity(capacity);
+    let first_line_length = DEFAULT_TEXT_WIDTH - shorten_first - format_text_len;
+
+    let (total_lines, bytes) =
+        if let Some((first, rest)) = bytes.split_at_checked(first_line_length) {
+            out.extend_from_slice(prefix(Some(0)).as_bytes());
+            out.extend_from_slice(first);
+            out.extend_from_slice(suffix);
+            if !rest.is_empty() {
+                out.push(b'\n');
+            }
+            (1, rest)
+        } else {
+            (0, bytes)
+        };
+
+    for (line, chunk) in bytes
+        .chunks(DEFAULT_TEXT_WIDTH - format_text_len)
+        .enumerate()
+    {
+        let line = line + total_lines;
+        out.extend_from_slice(prefix(Some(line)).as_bytes());
         out.extend_from_slice(chunk);
+
         if line + 1 != lines {
-            // do not end last line with newline to give caller control over doing so.
+            out.extend_from_slice(suffix);
             out.push(b'\n');
+        } else if !skip_last_suffix {
+            out.extend_from_slice(suffix);
         }
     }

-    // SAFETY: base64 encoded, which is 7-bit chars (ASCII) and thus always valid UTF8
+    // SAFETY: all input slices were valid utf-8 string slices
     unsafe { String::from_utf8_unchecked(out) }
 }

@@ -104,24 +164,41 @@ impl Attachment<'_> {

         let mut attachment = String::new();

-        let encoded_filename = if self.filename.is_ascii() {
-            &self.filename
-        } else {
-            &format!("=?utf-8?B?{}?=", proxmox_base64::encode(&self.filename))
-        };
-
         let _ = writeln!(attachment, "\n--{file_boundary}");
-        let _ = writeln!(
-            attachment,
-            "Content-Type: {}; name=\"{encoded_filename}\"",
-            self.mime,
-        );

-        // both `filename` and `filename*` are included for additional compatibility
+        let _ = write!(attachment, "Content-Type: {};\n\tname=\"", self.mime);
+
+        if self.filename.is_ascii() {
+            let _ = write!(attachment, "{}", &self.filename);
+        } else {
+            let encoded = proxmox_base64::encode(&self.filename);
+            let prefix_fn = |line| {
+                if Some(0) == line {
+                    "=?utf-8?B?"
+                } else {
+                    "\t=?utf-8?B?"
+                }
+                .into()
+            };
+
+            // minus one here as the first line isn't indented
+            let skip_first = "\tname=\"".len() - 1;
+
+            let _ = write!(
+                attachment,
+                "{}",
+                format_text(&encoded, prefix_fn, "?=", skip_first, false)
+            );
+        }
+
+        // should be fine to add one here, the last line should be at most 72 chars. according to
+        // rfc 2045 encoded output lines should be "no more than 76 characters each"
+        let _ = writeln!(attachment, "\"");
+
         let _ = writeln!(
             attachment,
-            "Content-Disposition: attachment; filename=\"{encoded_filename}\";\n\tfilename*=UTF-8''{}",
-            utf8_percent_encode(&self.filename, RFC5987SET)
+            "Content-Disposition: attachment;\n{}",
+            encode_filename_formatted(&self.filename)
         );

         attachment.push_str("Content-Transfer-Encoding: base64\n\n");
@@ -809,9 +886,10 @@ Content-Transfer-Encoding: 7bit
 Lorem Ipsum Dolor Sit
 Amet
 ------_=_NextPart_001_1732806251
-Content-Type: application/octet-stream; name="deadbeef.bin"
-Content-Disposition: attachment; filename="deadbeef.bin";
-	filename*=UTF-8''deadbeef.bin
+Content-Type: application/octet-stream;
+	name="deadbeef.bin"
+Content-Disposition: attachment;
+	filename*0*=UTF-8''deadbeef.bin
 Content-Transfer-Encoding: base64

 3q2+796tvu/erb7v3q3erb7v3q2+796tvu/erd6tvu/erb7v3q2+796t3q2+796tvu/erb7v
@@ -838,7 +916,7 @@ Content-Transfer-Encoding: base64
         )
         .with_recipient_and_name("Receiver Name", "receiver@example.com")
         .with_attachment("deadbeef.bin", "application/octet-stream", &bin)
-        .with_attachment("🐄💀.bin", "image/bmp", &bin)
+        .with_attachment("🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀🐄💀.bin", "image/bmp", &bin)
         .with_html_alt("<html lang=\"de-at\"><head></head><body>\n\t<pre>\n\t\tLorem Ipsum Dolor Sit Amet\n\t</pre>\n</body></html>");

         let body = mail.format_mail(1732806251).expect("could not format mail");
@@ -879,17 +957,28 @@ Content-Transfer-Encoding: 7bit
 </body></html>
 ------_=_NextPart_002_1732806251--
 ------_=_NextPart_001_1732806251
-Content-Type: application/octet-stream; name="deadbeef.bin"
-Content-Disposition: attachment; filename="deadbeef.bin";
-	filename*=UTF-8''deadbeef.bin
+Content-Type: application/octet-stream;
+	name="deadbeef.bin"
+Content-Disposition: attachment;
+	filename*0*=UTF-8''deadbeef.bin
 Content-Transfer-Encoding: base64

 3q2+796tvu/erb7v3q3erb7v3q2+796tvu/erd6tvu/erb7v3q2+796t3q2+796tvu/erb7v
 3q2+796tvu8=
 ------_=_NextPart_001_1732806251
-Content-Type: image/bmp; name="=?utf-8?B?8J+QhPCfkoAuYmlu?="
-Content-Disposition: attachment; filename="=?utf-8?B?8J+QhPCfkoAuYmlu?=";
-	filename*=UTF-8''%F0%9F%90%84%F0%9F%92%80.bin
+Content-Type: image/bmp;
+	name="=?utf-8?B?8J+QhPCfkoDwn5CE8J+SgPCfkITwn5KA8J+QhPCfkoDwn5CE8J+Sg?=
+	=?utf-8?B?PCfkITwn5KA8J+QhPCfkoDwn5CE8J+SgPCfkITwn5KA8J+QhPCfkoDwn5CE?=
+	=?utf-8?B?8J+SgPCfkITwn5KA8J+QhPCfkoDwn5CE8J+SgPCfkITwn5KA8J+QhPCfkoA?=
+	=?utf-8?B?uYmlu?="
+Content-Disposition: attachment;
+	filename*0*=UTF-8''%F0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%92%80%F;
+	filename*1*=0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%92%80%F0%9F%90%8;
+	filename*2*=4%F0%9F%92%80%F0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%9;
+	filename*3*=2%80%F0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%92%80%F0%9;
+	filename*4*=F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F;
+	filename*5*=0%9F%92%80%F0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%92%8;
+	filename*6*=0%F0%9F%90%84%F0%9F%92%80%F0%9F%90%84%F0%9F%92%80.bin
 Content-Transfer-Encoding: base64

 3q2+796tvu/erb7v3q3erb7v3q2+796tvu/erd6tvu/erb7v3q2+796t3q2+796tvu/erb7v
@@ -997,17 +1086,19 @@ PGh0bWwgbGFuZz0iZGUtYXQiPjxoZWFkPjwvaGVhZD48Ym9keT4KCTxwcmU+CgkJTG9yZW0g
 SXBzdW0gRMO2bG9yIFNpdCBBbWV0Cgk8L3ByZT4KPC9ib2R5PjwvaHRtbD4=
 ------_=_NextPart_002_1732806251--
 ------_=_NextPart_001_1732806251
-Content-Type: application/octet-stream; name="deadbeef.bin"
-Content-Disposition: attachment; filename="deadbeef.bin";
-	filename*=UTF-8''deadbeef.bin
+Content-Type: application/octet-stream;
+	name="deadbeef.bin"
+Content-Disposition: attachment;
+	filename*0*=UTF-8''deadbeef.bin
 Content-Transfer-Encoding: base64

 3q2+796tvu/erb7v3q3erb7v3q2+796tvu/erd6tvu/erb7v3q2+796t3q2+796tvu/erb7v
 3q2+796tvu8=
 ------_=_NextPart_001_1732806251
-Content-Type: image/bmp; name="=?utf-8?B?8J+QhPCfkoAuYmlu?="
-Content-Disposition: attachment; filename="=?utf-8?B?8J+QhPCfkoAuYmlu?=";
-	filename*=UTF-8''%F0%9F%90%84%F0%9F%92%80.bin
+Content-Type: image/bmp;
+	name="=?utf-8?B?8J+QhPCfkoAuYmlu?="
+Content-Disposition: attachment;
+	filename*0*=UTF-8''%F0%9F%90%84%F0%9F%92%80.bin
 Content-Transfer-Encoding: base64

 3q2+796tvu/erb7v3q3erb7v3q2+796tvu/erd6tvu/erb7v3q2+796t3q2+796tvu/erb7v
--
2.47.3





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