diff --git a/crates/ruff_server/src/server/api.rs b/crates/ruff_server/src/server/api.rs
index d649379d48317..38166fdf68795 100644
--- a/crates/ruff_server/src/server/api.rs
+++ b/crates/ruff_server/src/server/api.rs
@@ -55,6 +55,7 @@ pub(super) fn request<'a>(req: server::Request) -> Task<'a> {
     }
     .unwrap_or_else(|err| {
         tracing::error!("Encountered error when routing request with ID {id}: {err}");
+        show_err_msg!("Ruff failed to handle a request from the editor. Check the error log for more details.");
         let result: Result<()> = Err(err);
         Task::immediate(id, result)
     })
@@ -84,6 +85,7 @@ pub(super) fn notification<'a>(notif: server::Notification) -> Task<'a> {
     }
     .unwrap_or_else(|err| {
         tracing::error!("Encountered error when routing notification: {err}");
+        show_err_msg!("Ruff failed to handle a notification from the editor. Check the error log for more details.");
         Task::nothing()
     })
 }
@@ -122,6 +124,7 @@ fn local_notification_task<'a, N: traits::SyncNotificationHandler>(
     Ok(Task::local(move |session, notifier, _, _| {
         if let Err(err) = N::run(session, notifier, params) {
             tracing::error!("An error occurred while running {id}: {err}");
+            show_err_msg!("Ruff encountered a problem. Check the error log for more details.");
         }
     }))
 }
@@ -140,6 +143,7 @@ fn background_notification_thread<'a, N: traits::BackgroundDocumentNotificationH
         Box::new(move |notifier, _| {
             if let Err(err) = N::run_with_snapshot(snapshot, notifier, params) {
                 tracing::error!("An error occurred while running {id}: {err}");
+                show_err_msg!("Ruff encountered a problem. Check the error log for more details.");
             }
         })
     }))
@@ -182,6 +186,10 @@ fn respond<Req>(
 ) where
     Req: traits::RequestHandler,
 {
+    if let Err(err) = &result {
+        tracing::error!("An error occurred with result ID {id}: {err}");
+        show_err_msg!("Ruff encountered a problem. Check the error log for more details.");
+    }
     if let Err(err) = responder.respond(id, result) {
         tracing::error!("Failed to send response: {err}");
     }
diff --git a/crates/ruff_server/src/server/api/requests/execute_command.rs b/crates/ruff_server/src/server/api/requests/execute_command.rs
index c8cdb7fdec05a..28b309b5978e0 100644
--- a/crates/ruff_server/src/server/api/requests/execute_command.rs
+++ b/crates/ruff_server/src/server/api/requests/execute_command.rs
@@ -145,7 +145,8 @@ fn apply_edit(
                 let reason = response
                     .failure_reason
                     .unwrap_or_else(|| String::from("unspecified reason"));
-                tracing::error!("Failed to apply workspace edit: {}", reason);
+                tracing::error!("Failed to apply workspace edit: {reason}");
+                show_err_msg!("Ruff was unable to apply edits: {reason}");
             }
             Task::nothing()
         },
diff --git a/crates/ruff_server/src/session/settings.rs b/crates/ruff_server/src/session/settings.rs
index a29692a63c419..de30b922d75cf 100644
--- a/crates/ruff_server/src/session/settings.rs
+++ b/crates/ruff_server/src/session/settings.rs
@@ -100,6 +100,7 @@ impl AllSettings {
             serde_json::from_value(options)
                 .map_err(|err| {
                     tracing::error!("Failed to deserialize initialization options: {err}. Falling back to default client settings...");
+                    show_err_msg!("Ruff received invalid client settings - falling back to default client settings.");
                 })
                 .unwrap_or_default(),
         )