diff --git a/src/chat.rs b/src/chat.rs
index 1d787a1d0..f21ce144a 100644
--- a/src/chat.rs
+++ b/src/chat.rs
@@ -2669,10 +2669,12 @@ pub(crate) async fn get_chat_id_by_grpid(
 /// Adds a message to device chat.
 ///
 /// Optional `label` can be provided to ensure that message is added only once.
-pub async fn add_device_msg(
+/// If `important` is true, a notification will be sent.
+pub async fn add_device_msg_with_importance(
     context: &Context,
     label: Option<&str>,
     msg: Option<&mut Message>,
+    important: bool,
 ) -> Result<MsgId, Error> {
     ensure!(
         label.is_some() || msg.is_some(),
@@ -2732,12 +2734,24 @@ pub async fn add_device_msg(
     }
 
     if !msg_id.is_unset() {
-        context.emit_event(Event::IncomingMsg { chat_id, msg_id });
+        if important {
+            context.emit_event(Event::IncomingMsg { chat_id, msg_id });
+        } else {
+            context.emit_event(Event::MsgsChanged { chat_id, msg_id });
+        }
     }
 
     Ok(msg_id)
 }
 
+pub async fn add_device_msg(
+    context: &Context,
+    label: Option<&str>,
+    msg: Option<&mut Message>,
+) -> Result<MsgId, Error> {
+    add_device_msg_with_importance(context, label, msg, false).await
+}
+
 pub async fn was_device_msg_ever_added(context: &Context, label: &str) -> Result<bool, Error> {
     ensure!(!label.is_empty(), "empty label");
     if let Ok(()) = context
diff --git a/src/config.rs b/src/config.rs
index 2c59d6435..ddb266e7b 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -117,6 +117,11 @@ pub enum Config {
 
     #[strum(serialize = "sys.config_keys")]
     SysConfigKeys,
+
+    #[strum(props(default = "0"))]
+    /// Whether we send a warning if the password is wrong (set to false when we send a warning
+    /// because we do not want to send a second warning)
+    NotifyAboutWrongPw,
 }
 
 impl Context {
diff --git a/src/configure/mod.rs b/src/configure/mod.rs
index 4894ee747..7afa6be98 100644
--- a/src/configure/mod.rs
+++ b/src/configure/mod.rs
@@ -70,6 +70,7 @@ impl Context {
 
         let mut param = LoginParam::from_database(self, "").await;
         let success = configure(self, &mut param).await;
+        self.set_config(Config::NotifyAboutWrongPw, None).await?;
 
         if let Some(provider) = provider::get_provider_info(&param.addr) {
             if let Some(config_defaults) = &provider.config_defaults {
@@ -100,11 +101,12 @@ impl Context {
 
         match success {
             Ok(_) => {
+                self.set_config(Config::NotifyAboutWrongPw, Some("1"))
+                    .await?;
                 progress!(self, 1000);
                 Ok(())
             }
             Err(err) => {
-                error!(self, "Configure Failed: {}", err);
                 progress!(self, 0);
                 Err(err)
             }
@@ -457,7 +459,10 @@ async fn try_imap_connections(
         .await
         .is_ok()
     {
-        return Ok(()); // we directly return here if it was autoconfig or the connection succeeded
+        return Ok(());
+    }
+    if was_autoconfig {
+        bail!("autoconfig did not succeed");
     }
 
     progress!(context, 670);
@@ -491,7 +496,7 @@ async fn try_imap_connection(
         return Ok(());
     }
     if was_autoconfig {
-        return Ok(());
+        bail!("autoconfig did not succeed");
     }
 
     progress!(context, 650 + variation * 30);
@@ -551,7 +556,7 @@ async fn try_smtp_connections(
         return Ok(());
     }
     if was_autoconfig {
-        return Ok(());
+        bail!("No SMTP connection");
     }
     progress!(context, 850);
 
diff --git a/src/context.rs b/src/context.rs
index 016c27d4f..5458282bf 100644
--- a/src/context.rs
+++ b/src/context.rs
@@ -53,6 +53,8 @@ pub struct InnerContext {
     pub(crate) generating_key_mutex: Mutex<()>,
     /// Mutex to enforce only a single running oauth2 is running.
     pub(crate) oauth2_mutex: Mutex<()>,
+    /// Mutex to prevent a race condition when a "your pw is wrong" warning is sent, resulting in multiple messeges being sent.
+    pub(crate) wrong_pw_warning_mutex: Mutex<()>,
     pub(crate) translated_stockstrings: RwLock<HashMap<usize, String>>,
     pub(crate) events: Events,
 
@@ -120,6 +122,7 @@ impl Context {
             last_smeared_timestamp: RwLock::new(0),
             generating_key_mutex: Mutex::new(()),
             oauth2_mutex: Mutex::new(()),
+            wrong_pw_warning_mutex: Mutex::new(()),
             translated_stockstrings: RwLock::new(HashMap::new()),
             events: Events::default(),
             scheduler: RwLock::new(Scheduler::Stopped),
diff --git a/src/imap/mod.rs b/src/imap/mod.rs
index cd9779c4a..bb095d2e6 100644
--- a/src/imap/mod.rs
+++ b/src/imap/mod.rs
@@ -28,7 +28,7 @@ use crate::mimeparser;
 use crate::oauth2::dc_get_oauth2_access_token;
 use crate::param::Params;
 use crate::provider::get_provider_info;
-use crate::{scheduler::InterruptInfo, stock::StockMessage};
+use crate::{chat, scheduler::InterruptInfo, stock::StockMessage};
 
 mod client;
 mod idle;
@@ -36,6 +36,7 @@ pub mod select_folder;
 mod session;
 
 use client::Client;
+use message::Message;
 use session::Session;
 
 type Result<T> = std::result::Result<T, Error>;
@@ -116,6 +117,7 @@ pub struct Imap {
     connected: bool,
     interrupt: Option<stop_token::StopSource>,
     should_reconnect: bool,
+    login_failed_once: bool,
 }
 
 #[derive(Debug)]
@@ -189,6 +191,7 @@ impl Imap {
             connected: Default::default(),
             interrupt: Default::default(),
             should_reconnect: Default::default(),
+            login_failed_once: Default::default(),
         }
     }
 
@@ -293,18 +296,40 @@ impl Imap {
                 // needs to be set here to ensure it is set on reconnects.
                 self.connected = true;
                 self.session = Some(session);
+                self.login_failed_once = false;
                 Ok(())
             }
+
             Err((err, _)) => {
                 let imap_user = self.config.imap_user.to_owned();
                 let message = context
                     .stock_string_repl_str(StockMessage::CannotLogin, &imap_user)
                     .await;
 
-                emit_event!(
-                    context,
-                    Event::ErrorNetwork(format!("{} ({})", message, err))
-                );
+                warn!(context, "{} ({})", message, err);
+                emit_event!(context, Event::ErrorNetwork(message.clone()));
+
+                let lock = context.wrong_pw_warning_mutex.lock().await;
+                if self.login_failed_once
+                    && context.get_config_bool(Config::NotifyAboutWrongPw).await
+                {
+                    if let Err(e) = context.set_config(Config::NotifyAboutWrongPw, None).await {
+                        warn!(context, "{}", e);
+                    }
+                    drop(lock);
+
+                    let mut msg = Message::new(Viewtype::Text);
+                    msg.text = Some(message);
+                    if let Err(e) =
+                        chat::add_device_msg_with_importance(context, None, Some(&mut msg), true)
+                            .await
+                    {
+                        warn!(context, "{}", e);
+                    }
+                } else {
+                    self.login_failed_once = true;
+                }
+
                 self.trigger_reconnect();
                 Err(Error::LoginFailed(format!("cannot login as {}", imap_user)))
             }
diff --git a/src/smtp/mod.rs b/src/smtp/mod.rs
index 1296c796c..2e4ad6e57 100644
--- a/src/smtp/mod.rs
+++ b/src/smtp/mod.rs
@@ -183,7 +183,7 @@ impl Smtp {
                 .stock_string_repl_str2(
                     StockMessage::ServerResponse,
                     format!("SMTP {}:{}", domain, port),
-                    format!("{}, ({:?})", err.to_string(), err),
+                    err.to_string(),
                 )
                 .await;
 
diff --git a/src/stock.rs b/src/stock.rs
index 9754b1d3a..84ef72f09 100644
--- a/src/stock.rs
+++ b/src/stock.rs
@@ -130,7 +130,9 @@ pub enum StockMessage {
     ))]
     AcSetupMsgBody = 43,
 
-    #[strum(props(fallback = "Cannot login as %1$s."))]
+    #[strum(props(
+        fallback = "Cannot login as \"%1$s\". Please check if the email address and the password are correct."
+    ))]
     CannotLogin = 60,
 
     #[strum(props(fallback = "Could not connect to %1$s: %2$s"))]