diff --git a/src/job.rs b/src/job.rs
index 6eb4997f1..cb39b6823 100644
--- a/src/job.rs
+++ b/src/job.rs
@@ -3,6 +3,7 @@
 //! This module implements a job queue maintained in the SQLite database
 //! and job types.
 
+use std::env;
 use std::fmt;
 use std::future::Future;
 
@@ -31,6 +32,7 @@ use crate::message::{self, Message, MessageState};
 use crate::mimefactory::MimeFactory;
 use crate::param::*;
 use crate::smtp::Smtp;
+use crate::upload::upload_file;
 use crate::{scheduler::InterruptInfo, sql};
 
 // results in ~3 weeks for the last backoff timespan
@@ -726,7 +728,25 @@ pub async fn send_msg_job(context: &Context, msg_id: MsgId) -> Result<Option<Job
         }
     };
 
-    let mimefactory = MimeFactory::from_msg(context, &msg, attach_selfavatar).await?;
+    // Upload file if DCC_UPLOAD_URL is set.
+    // See upload-server folder for an example.
+    // TODO: Move into send_msg_to_smtp job.
+    let mut did_upload_file = false;
+    if let Some(file) = msg.get_file(context) {
+        if let Ok(endpoint) = env::var("DCC_UPLOAD_URL") {
+            info!(context, "Upload file attachement to {}", endpoint);
+            let file_url = upload_file(context, endpoint, file).await?;
+            let text = msg.text.clone().unwrap_or("".into());
+            let suffix = format!("\n\nFile attachement: {}", file_url);
+            msg.set_text(Some(format!("{}{}", text, suffix)));
+            did_upload_file = true;
+        }
+    }
+
+    let mut mimefactory = MimeFactory::from_msg(context, &msg, attach_selfavatar).await?;
+    if did_upload_file {
+        mimefactory.set_include_file(false);
+    }
 
     let mut recipients = mimefactory.recipients();
 
diff --git a/src/lib.rs b/src/lib.rs
index 8ada41560..e8f47b00c 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -67,6 +67,7 @@ mod simplify;
 mod smtp;
 pub mod stock;
 mod token;
+pub(crate) mod upload;
 #[macro_use]
 mod dehtml;
 
diff --git a/src/mimefactory.rs b/src/mimefactory.rs
index cdff779fa..308396c9b 100644
--- a/src/mimefactory.rs
+++ b/src/mimefactory.rs
@@ -50,6 +50,7 @@ pub struct MimeFactory<'a, 'b> {
     context: &'a Context,
     last_added_location_id: u32,
     attach_selfavatar: bool,
+    include_file: bool,
 }
 
 /// Result of rendering a message, ready to be submitted to a send job.
@@ -159,6 +160,7 @@ impl<'a, 'b> MimeFactory<'a, 'b> {
             last_added_location_id: 0,
             attach_selfavatar,
             context,
+            include_file: true,
         };
         Ok(factory)
     }
@@ -206,6 +208,7 @@ impl<'a, 'b> MimeFactory<'a, 'b> {
             req_mdn: false,
             last_added_location_id: 0,
             attach_selfavatar: false,
+            include_file: true,
         };
 
         Ok(res)
@@ -409,6 +412,10 @@ impl<'a, 'b> MimeFactory<'a, 'b> {
             .collect()
     }
 
+    pub fn set_include_file(&mut self, include_file: bool) {
+        self.include_file = include_file
+    }
+
     pub async fn render(mut self) -> Result<RenderedEmail, Error> {
         // Headers that are encrypted
         // - Chat-*, except Chat-Version
@@ -900,7 +907,7 @@ impl<'a, 'b> MimeFactory<'a, 'b> {
         let mut parts = Vec::new();
 
         // add attachment part
-        if chat::msgtype_has_file(self.msg.viewtype) {
+        if chat::msgtype_has_file(self.msg.viewtype) && self.include_file {
             if !is_file_size_okay(context, &self.msg).await {
                 bail!(
                     "Message exceeds the recommended {} MB.",
diff --git a/src/upload.rs b/src/upload.rs
new file mode 100644
index 000000000..481250f02
--- /dev/null
+++ b/src/upload.rs
@@ -0,0 +1,17 @@
+use crate::context::Context;
+use crate::error::{bail, Result};
+use async_std::path::PathBuf;
+
+/// Upload file to a HTTP upload endpoint.
+pub async fn upload_file(_context: &Context, endpoint: String, file: PathBuf) -> Result<String> {
+    // TODO: Use tokens for upload, encrypt file with PGP.
+    let response = surf::post(endpoint).body_file(file)?.await;
+    if let Err(err) = response {
+        bail!("Upload failed: {}", err);
+    }
+    let mut response = response.unwrap();
+    match response.body_string().await {
+        Ok(string) => Ok(string),
+        Err(err) => bail!("Invalid response from upload: {}", err),
+    }
+}