diff --git a/deltachat-ffi/src/lib.rs b/deltachat-ffi/src/lib.rs
index ea25b5979..eaa15f8f4 100644
--- a/deltachat-ffi/src/lib.rs
+++ b/deltachat-ffi/src/lib.rs
@@ -1245,8 +1245,11 @@ pub unsafe extern "C" fn dc_forward_msgs(
 
     let ffi_context = &*context;
     ffi_context
-        .with_inner(|ctx| chat::forward_msgs(ctx, ids, chat_id))
-        .unwrap_or_log_default(ctx, "Failed to forard message")
+        .with_inner(|ctx| {
+            chat::forward_msgs(ctx, ids, chat_id)
+                .unwrap_or_log_default(ctx, "Failed to forward message")
+        })
+        .unwrap_or_default()
 }
 
 #[no_mangle]
diff --git a/src/chat.rs b/src/chat.rs
index 166d2489f..3d66c63e0 100644
--- a/src/chat.rs
+++ b/src/chat.rs
@@ -805,8 +805,7 @@ pub fn send_msg(context: &Context, chat_id: u32, msg: &mut Message) -> Result<u3
                     break;
                 } else {
                     if let Ok(mut copy) = Message::load_from_db(context, id as u32) {
-                        // TODO: handle cleanup and return early instead
-                        send_msg(context, 0, &mut copy).unwrap();
+                        send_msg(context, 0, &mut copy)?;
                     }
                 }
             }
@@ -1421,7 +1420,7 @@ pub(crate) fn add_contact_to_chat_ex(
         msg.param.set_int(Param::Cmd, 4);
         msg.param.set(Param::Arg, contact.get_addr());
         msg.param.set_int(Param::Arg2, from_handshake.into());
-        msg.id = send_msg(context, chat_id, &mut msg).unwrap_or_default();
+        msg.id = send_msg(context, chat_id, &mut msg)?;
         context.call_cb(Event::MsgsChanged {
             chat_id,
             msg_id: msg.id,
@@ -1532,7 +1531,7 @@ pub fn remove_contact_from_chat(
                         }
                         msg.param.set_int(Param::Cmd, 5);
                         msg.param.set(Param::Arg, contact.get_addr());
-                        msg.id = send_msg(context, chat_id, &mut msg).unwrap_or_default();
+                        msg.id = send_msg(context, chat_id, &mut msg)?;
                         context.call_cb(Event::MsgsChanged {
                             chat_id,
                             msg_id: msg.id,
@@ -1629,7 +1628,7 @@ pub fn set_chat_name(
                     if !chat.name.is_empty() {
                         msg.param.set(Param::Arg, &chat.name);
                     }
-                    msg.id = send_msg(context, chat_id, &mut msg).unwrap_or_default();
+                    msg.id = send_msg(context, chat_id, &mut msg)?;
                     context.call_cb(Event::MsgsChanged {
                         chat_id,
                         msg_id: msg.id,
@@ -1698,7 +1697,7 @@ pub fn set_chat_profile_image(
                     "",
                     DC_CONTACT_ID_SELF,
                 ));
-                msg.id = send_msg(context, chat_id, &mut msg).unwrap_or_default();
+                msg.id = send_msg(context, chat_id, &mut msg)?;
                 emit_event!(
                     context,
                     Event::MsgsChanged {
diff --git a/src/job.rs b/src/job.rs
index b76e13ab6..25ef9e8fe 100644
--- a/src/job.rs
+++ b/src/job.rs
@@ -167,32 +167,36 @@ impl Job {
                     // was sent we need to mark it in the database ASAP as we
                     // otherwise might send it twice.
                     let mut sock = context.smtp.lock().unwrap();
-                    if !sock.send(context, recipients_list, body) {
-                        sock.disconnect();
-                        self.try_again_later(-1i32, sock.error.clone());
-                    } else {
-                        // smtp success, update DB as quick as possible
-                        if 0 != self.foreign_id {
-                            message::update_msg_state(
-                                context,
-                                self.foreign_id,
-                                MessageState::OutDelivered,
-                            );
-                            let chat_id: i32 = context
-                                .sql
-                                .query_get_value(
-                                    context,
-                                    "SELECT chat_id FROM msgs WHERE id=?",
-                                    params![self.foreign_id as i32],
-                                )
-                                .unwrap_or_default();
-                            context.call_cb(Event::MsgDelivered {
-                                chat_id: chat_id as u32,
-                                msg_id: self.foreign_id,
-                            });
+                    match sock.send(context, recipients_list, body) {
+                        Err(err) => {
+                            sock.disconnect();
+                            warn!(context, "smtp failed: {}", err);
+                            self.try_again_later(-1i32, Some(err.to_string()));
+                        }
+                        Ok(()) => {
+                            // smtp success, update db ASAP, then delete smtp file
+                            if 0 != self.foreign_id {
+                                message::update_msg_state(
+                                    context,
+                                    self.foreign_id,
+                                    MessageState::OutDelivered,
+                                );
+                                let chat_id: i32 = context
+                                    .sql
+                                    .query_get_value(
+                                        context,
+                                        "SELECT chat_id FROM msgs WHERE id=?",
+                                        params![self.foreign_id as i32],
+                                    )
+                                    .unwrap_or_default();
+                                context.call_cb(Event::MsgDelivered {
+                                    chat_id: chat_id as u32,
+                                    msg_id: self.foreign_id,
+                                });
+                            }
+                            // now also delete the generated file
+                            dc_delete_file(context, filename);
                         }
-                        // now also delete the generated file
-                        dc_delete_file(context, filename);
                     }
                 } else {
                     warn!(context, "Missing recipients for job {}", self.job_id,);
@@ -214,7 +218,7 @@ impl Job {
         if !inbox.is_connected() {
             connect_to_inbox(context, &inbox);
             if !inbox.is_connected() {
-                self.try_again_later(3, None);
+                self.try_again_later(3, Some("could not connect".into()));
                 return;
             }
         }
@@ -612,10 +616,6 @@ pub fn job_action_exists(context: &Context, action: Action) -> bool {
 pub fn job_send_msg(context: &Context, msg_id: u32) -> Result<(), Error> {
     let mut mimefactory = MimeFactory::load_msg(context, msg_id)?;
 
-    ensure!(!mimefactory.recipients_addr.is_empty(), 
-            "msg {} has no recipients, can not smtp-sent", msg_id
-    );
-
     if chat::msgtype_has_file(mimefactory.msg.type_0) {
         let file_param = mimefactory
             .msg
@@ -672,6 +672,15 @@ pub fn job_send_msg(context: &Context, msg_id: u32) -> Result<(), Error> {
             .recipients_addr
             .push(mimefactory.from_addr.to_string());
     }
+
+    if mimefactory.recipients_addr.is_empty() {
+        warn!(
+            context,
+            "message {} has no recipient, skipping smtp-send", msg_id
+        );
+        return Ok(());
+    }
+
     if mimefactory.out_gossiped {
         chat::set_gossiped_timestamp(context, mimefactory.msg.chat_id, time());
     }
diff --git a/src/smtp.rs b/src/smtp.rs
index f2287b749..5d8ba4654 100644
--- a/src/smtp.rs
+++ b/src/smtp.rs
@@ -3,6 +3,7 @@ use lettre::*;
 
 use crate::constants::*;
 use crate::context::Context;
+use crate::error::Error;
 use crate::events::Event;
 use crate::login_param::LoginParam;
 use crate::oauth2::*;
@@ -14,7 +15,6 @@ pub struct Smtp {
     transport_connected: bool,
     /// Email address we are sending from.
     from: Option<EmailAddress>,
-    pub error: Option<String>,
 }
 
 impl Smtp {
@@ -24,7 +24,6 @@ impl Smtp {
             transport: None,
             transport_connected: false,
             from: None,
-            error: None,
         }
     }
 
@@ -132,11 +131,19 @@ impl Smtp {
         context: &Context,
         recipients: Vec<EmailAddress>,
         message: Vec<u8>,
-    ) -> bool {
+    ) -> Result<(), Error> {
         let message_len = message.len();
 
+        let recipients_display = recipients
+            .iter()
+            .map(|x| format!("{}", x))
+            .collect::<Vec<String>>()
+            .join(",");
+
         if let Some(ref mut transport) = self.transport {
-            let envelope = Envelope::new(self.from.clone(), recipients).expect("invalid envelope");
+            let envelope = Envelope::new(self.from.clone(), recipients);
+            ensure!(envelope.is_ok(), "internal smtp-message construction fail");
+            let envelope = envelope.unwrap();
             let mail = SendableEmail::new(
                 envelope,
                 "mail-id".into(), // TODO: random id
@@ -145,24 +152,22 @@ impl Smtp {
 
             match transport.send(mail) {
                 Ok(_) => {
-                    context.call_cb(Event::SmtpMessageSent(
-                        "Message was sent to SMTP server".into(),
-                    ));
+                    context.call_cb(Event::SmtpMessageSent(format!(
+                        "Message len={} was smtp-sent to {}",
+                        message_len, recipients_display
+                    )));
                     self.transport_connected = true;
-                    true
+                    return Ok(());
                 }
                 Err(err) => {
-                    warn!(
-                        context,
-                        "SMTP failed message size {}, error: {}", message_len, err
-                    );
-                    self.error = Some(format!("{}", err));
-                    false
+                    bail!("SMTP failed len={}: error: {}", message_len, err);
                 }
             }
         } else {
-            warn!(context, "SMTP Failed to send message to {:?}", recipients);
-            false
+            bail!(
+                "uh? SMTP has no transport,  failed to send to {:?}",
+                recipients_display
+            );
         }
     }
 }