diff --git a/src/blob.rs b/src/blob.rs
index f3059ec0cc..44a4577ffb 100644
--- a/src/blob.rs
+++ b/src/blob.rs
@@ -1423,7 +1423,7 @@ mod tests {
                 .set_config(Config::MediaQuality, Some(media_quality_config))
                 .await?;
             let file = alice.get_blobdir().join("file").with_extension(extension);
-            let file_name = format!("file{extension}");
+            let file_name = format!("file.{extension}");
 
             fs::write(&file, &bytes)
                 .await
@@ -1457,6 +1457,8 @@ mod tests {
             alice_msg.save_file(&alice, &file_saved).await?;
             check_image_size(file_saved, compressed_width, compressed_height);
 
+            println!("{}", sent.payload());
+
             let bob_msg = bob.recv_msg(&sent).await;
             assert_eq!(bob_msg.get_viewtype(), Viewtype::Image);
             assert_eq!(bob_msg.get_width() as u32, compressed_width);
diff --git a/src/chat.rs b/src/chat.rs
index 320fffb854..7eb5f312f0 100644
--- a/src/chat.rs
+++ b/src/chat.rs
@@ -893,13 +893,12 @@ impl ChatId {
                     .context("no file stored in params")?;
                 msg.param.set(Param::File, blob.as_name());
                 if msg.viewtype == Viewtype::File {
-                    if let Some((better_type, _)) =
-                        message::guess_msgtype_from_suffix(&blob.to_abs_path())
-                            // We do not do an automatic conversion to other viewtypes here so that
-                            // users can send images as "files" to preserve the original quality
-                            // (usually we compress images). The remaining conversions are done by
-                            // `prepare_msg_blob()` later.
-                            .filter(|&(vt, _)| vt == Viewtype::Webxdc || vt == Viewtype::Vcard)
+                    if let Some((better_type, _)) = message::guess_msgtype_from_suffix(msg)
+                        // We do not do an automatic conversion to other viewtypes here so that
+                        // users can send images as "files" to preserve the original quality
+                        // (usually we compress images). The remaining conversions are done by
+                        // `prepare_msg_blob()` later.
+                        .filter(|&(vt, _)| vt == Viewtype::Webxdc || vt == Viewtype::Vcard)
                     {
                         msg.viewtype = better_type;
                     }
@@ -2695,8 +2694,7 @@ async fn prepare_msg_blob(context: &Context, msg: &mut Message) -> Result<()> {
             // Typical conversions:
             // - from FILE to AUDIO/VIDEO/IMAGE
             // - from FILE/IMAGE to GIF */
-            if let Some((better_type, _)) = message::guess_msgtype_from_suffix(&blob.to_abs_path())
-            {
+            if let Some((better_type, _)) = message::guess_msgtype_from_suffix(msg) {
                 if better_type != Viewtype::Webxdc
                     || context
                         .ensure_sendable_webxdc_file(&blob.to_abs_path())
@@ -2729,6 +2727,7 @@ async fn prepare_msg_blob(context: &Context, msg: &mut Message) -> Result<()> {
             }
         }
         msg.param.set(Param::File, blob.as_name());
+        // TODO not sure if we still need the next part
         if let (Some(filename), Some(blob_ext)) = (msg.param.get(Param::Filename), blob.suffix()) {
             let stem = match filename.rsplit_once('.') {
                 Some((stem, _)) => stem,
@@ -2739,7 +2738,7 @@ async fn prepare_msg_blob(context: &Context, msg: &mut Message) -> Result<()> {
         }
 
         if !msg.param.exists(Param::MimeType) {
-            if let Some((_, mime)) = message::guess_msgtype_from_suffix(&blob.to_abs_path()) {
+            if let Some((_, mime)) = message::guess_msgtype_from_suffix(msg) {
                 msg.param.set(Param::MimeType, mime);
             }
         }
diff --git a/src/message.rs b/src/message.rs
index e35785269e..95363db402 100644
--- a/src/message.rs
+++ b/src/message.rs
@@ -626,8 +626,8 @@ impl Message {
     pub fn get_filemime(&self) -> Option<String> {
         if let Some(m) = self.param.get(Param::MimeType) {
             return Some(m.to_string());
-        } else if let Some(file) = self.param.get(Param::File) {
-            if let Some((_, mime)) = guess_msgtype_from_suffix(Path::new(file)) {
+        } else if self.param.exists(Param::File) {
+            if let Some((_, mime)) = guess_msgtype_from_suffix(self) {
                 return Some(mime.to_string());
             }
             // we have a file but no mimetype, let's use a generic one
@@ -1109,6 +1109,7 @@ impl Message {
     }
 
     /// Creates a new blob and sets it as a file associated with a message.
+    /// TODO this could also deduplicate
     pub async fn set_file_from_bytes(
         &mut self,
         context: &Context,
@@ -1459,7 +1460,14 @@ pub async fn get_msg_read_receipts(
         .await
 }
 
-pub(crate) fn guess_msgtype_from_suffix(path: &Path) -> Option<(Viewtype, &str)> {
+pub(crate) fn guess_msgtype_from_suffix(msg: &Message) -> Option<(Viewtype, &'static str)> {
+    msg.param
+        .get(Param::Filename)
+        .or_else(|| msg.param.get(Param::File))
+        .and_then(|file| guess_msgtype_from_path_suffix(Path::new(file)))
+}
+
+pub(crate) fn guess_msgtype_from_path_suffix(path: &Path) -> Option<(Viewtype, &'static str)> {
     let extension: &str = &path.extension()?.to_str()?.to_lowercase();
     let info = match extension {
         // before using viewtype other than Viewtype::File,
@@ -2201,15 +2209,15 @@ mod tests {
     #[test]
     fn test_guess_msgtype_from_suffix() {
         assert_eq!(
-            guess_msgtype_from_suffix(Path::new("foo/bar-sth.mp3")),
+            guess_msgtype_from_path_suffix(Path::new("foo/bar-sth.mp3")),
             Some((Viewtype::Audio, "audio/mpeg"))
         );
         assert_eq!(
-            guess_msgtype_from_suffix(Path::new("foo/file.html")),
+            guess_msgtype_from_path_suffix(Path::new("foo/file.html")),
             Some((Viewtype::File, "text/html"))
         );
         assert_eq!(
-            guess_msgtype_from_suffix(Path::new("foo/file.xdc")),
+            guess_msgtype_from_path_suffix(Path::new("foo/file.xdc")),
             Some((Viewtype::Webxdc, "application/webxdc+zip"))
         );
     }
diff --git a/src/mimefactory.rs b/src/mimefactory.rs
index 8780073041..c1feed2bcc 100644
--- a/src/mimefactory.rs
+++ b/src/mimefactory.rs
@@ -1,6 +1,7 @@
 //! # MIME message production.
 
 use std::collections::HashSet;
+use std::path::Path;
 
 use anyhow::{bail, Context as _, Result};
 use base64::Engine as _;
@@ -1511,14 +1512,19 @@ pub(crate) fn wrapped_base64_encode(buf: &[u8]) -> String {
 async fn build_body_file(
     context: &Context,
     msg: &Message,
-    base_name: &str,
+    base_name: &str, // TODO unused parameter
 ) -> Result<(PartBuilder, String)> {
+    let file_name = msg.get_filename().context("msg has no file")?;
+    let suffix = Path::new(&file_name)
+        .extension()
+        .and_then(|e| e.to_str())
+        .unwrap_or("dat");
+
     let blob = msg
         .param
         .get_blob(Param::File, context)
         .await?
         .context("msg has no file")?;
-    let suffix = blob.suffix().unwrap_or("dat");
 
     // Get file name to use for sending.  For privacy purposes, we do
     // not transfer the original filenames eg. for images; these names
@@ -1562,18 +1568,14 @@ async fn build_body_file(
                 ),
             &suffix
         ),
-        _ => msg
-            .param
-            .get(Param::Filename)
-            .unwrap_or_else(|| blob.as_file_name())
-            .to_string(),
+        _ => file_name,
     };
 
     /* check mimetype */
     let mimetype: mime::Mime = match msg.param.get(Param::MimeType) {
         Some(mtype) => mtype.parse()?,
         None => {
-            if let Some(res) = message::guess_msgtype_from_suffix(blob.as_rel_path()) {
+            if let Some(res) = message::guess_msgtype_from_suffix(msg) {
                 res.1.parse()?
             } else {
                 mime::APPLICATION_OCTET_STREAM
diff --git a/src/mimeparser.rs b/src/mimeparser.rs
index 4eb80b4d9e..3cbe32c130 100644
--- a/src/mimeparser.rs
+++ b/src/mimeparser.rs
@@ -2030,10 +2030,12 @@ fn get_mime_type(
         }
         mime::APPLICATION => match mimetype.subtype() {
             mime::OCTET_STREAM => match filename {
-                Some(filename) => match message::guess_msgtype_from_suffix(Path::new(&filename)) {
-                    Some((viewtype, _)) => viewtype,
-                    None => Viewtype::File,
-                },
+                Some(filename) => {
+                    match message::guess_msgtype_from_path_suffix(Path::new(&filename)) {
+                        Some((viewtype, _)) => viewtype,
+                        None => Viewtype::File,
+                    }
+                }
                 None => Viewtype::File,
             },
             _ => Viewtype::File,