diff --git a/deltachat-ffi/deltachat.h b/deltachat-ffi/deltachat.h
index caf95e2c6..4ccb61d51 100644
--- a/deltachat-ffi/deltachat.h
+++ b/deltachat-ffi/deltachat.h
@@ -353,6 +353,10 @@ char*           dc_get_blobdir               (const dc_context_t* context);
  * - `fetch_existing_msgs` = 1=fetch most recent existing messages on configure (default),
  *                    0=do not fetch existing messages on configure.
  *                    In both cases, existing recipients are added to the contact database.
+ * - `max_smtp_rcpt_to` = set the max. number of recipients that should be used for `RCPT TO:` smtp header.
+ *                    If a message needs to be sent to more recipients, multiple messages are sent out,
+ *                    each with exactly the same MIME-message (with `To:` mime headers that may contain all recipients)
+ *                    (defaults to 50)
  *
  * If you want to retrieve a value, use dc_get_config().
  *
diff --git a/src/config.rs b/src/config.rs
index 1ceff9a08..188e27fb9 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -69,6 +69,9 @@ pub enum Config {
     #[strum(props(default = "0"))] // also change MediaQuality.default() on changes
     MediaQuality,
 
+    #[strum(props(default = "50"))]
+    MaxSmtpRcptTo,
+
     /// If set to "1", on the first time `start_io()` is called after configuring,
     /// the newest existing messages are fetched.
     /// Existing recipients are added to the contact database regardless of this setting.
diff --git a/src/smtp/send.rs b/src/smtp/send.rs
index 4ffa64682..1767c70c4 100644
--- a/src/smtp/send.rs
+++ b/src/smtp/send.rs
@@ -3,6 +3,7 @@
 use super::Smtp;
 use async_smtp::*;
 
+use crate::config::Config;
 use crate::context::Context;
 use crate::events::EventType;
 use itertools::Itertools;
@@ -33,38 +34,41 @@ impl Smtp {
         job_id: u32,
     ) -> Result<()> {
         let message_len_bytes = message.len();
+        let chunk_size = context.get_config_int(Config::MaxSmtpRcptTo).await as usize;
 
-        let recipients_display = recipients.iter().map(|x| x.to_string()).join(",");
+        for recipients_chunk in recipients.chunks(chunk_size).into_iter() {
+            let recipients = recipients_chunk.to_vec();
+            let recipients_display = recipients.iter().map(|x| x.to_string()).join(",");
 
-        let envelope =
-            Envelope::new(self.from.clone(), recipients).map_err(Error::EnvelopeError)?;
-        let mail = SendableEmail::new(
-            envelope,
-            format!("{}", job_id), // only used for internal logging
-            message,
-        );
-
-        if let Some(ref mut transport) = self.transport {
-            // The timeout is 1min + 3min per MB.
-            let timeout = 60 + (180 * message_len_bytes / 1_000_000) as u64;
-            transport
-                .send_with_timeout(mail, Some(&Duration::from_secs(timeout)))
-                .await
-                .map_err(Error::SendError)?;
-
-            context.emit_event(EventType::SmtpMessageSent(format!(
-                "Message len={} was smtp-sent to {}",
-                message_len_bytes, recipients_display
-            )));
-            self.last_success = Some(std::time::SystemTime::now());
-
-            Ok(())
-        } else {
-            warn!(
-                context,
-                "uh? SMTP has no transport, failed to send to {}", recipients_display
+            let envelope =
+                Envelope::new(self.from.clone(), recipients).map_err(Error::EnvelopeError)?;
+            let mail = SendableEmail::new(
+                envelope,
+                format!("{}", job_id), // only used for internal logging
+                &message,
             );
-            Err(Error::NoTransport)
+
+            if let Some(ref mut transport) = self.transport {
+                // The timeout is 1min + 3min per MB.
+                let timeout = 60 + (180 * message_len_bytes / 1_000_000) as u64;
+                transport
+                    .send_with_timeout(mail, Some(&Duration::from_secs(timeout)))
+                    .await
+                    .map_err(Error::SendError)?;
+
+                context.emit_event(EventType::SmtpMessageSent(format!(
+                    "Message len={} was smtp-sent to {}",
+                    message_len_bytes, recipients_display
+                )));
+                self.last_success = Some(std::time::SystemTime::now());
+            } else {
+                warn!(
+                    context,
+                    "uh? SMTP has no transport, failed to send to {}", recipients_display
+                );
+                return Err(Error::NoTransport);
+            }
         }
+        Ok(())
     }
 }