2 files changed, 29 insertions, 15 deletions

diff --git a/cli/tools/repl/editor.rs b/cli/tools/repl/editor.rs
index 69fec9df0..73196d3f3 100644
--- a/cli/tools/repl/editor.rs
+++ b/cli/tools/repl/editor.rs
@@ -5,6 +5,7 @@ use crate::colors;
 use deno_ast::swc::parser::error::SyntaxError;
 use deno_ast::swc::parser::token::Token;
 use deno_ast::swc::parser::token::Word;
+use deno_core::anyhow::Context as _;
 use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use deno_core::serde_json;
@@ -27,6 +28,8 @@ use rustyline::{ConditionalEventHandler, Event, EventContext, RepeatCount};
 use rustyline_derive::{Helper, Hinter};
 use std::borrow::Cow;
 use std::path::PathBuf;
+use std::sync::atomic::AtomicBool;
+use std::sync::atomic::Ordering::Relaxed;
 use std::sync::Arc;
 
 use super::channel::RustylineSyncMessageSender;
@@ -368,10 +371,14 @@ impl Highlighter for EditorHelper {
 pub struct ReplEditor {
   inner: Arc<Mutex<Editor<EditorHelper>>>,
   history_file_path: PathBuf,
+  errored_on_history_save: Arc<AtomicBool>,
 }
 
 impl ReplEditor {
-  pub fn new(helper: EditorHelper, history_file_path: PathBuf) -> Self {
+  pub fn new(
+    helper: EditorHelper,
+    history_file_path: PathBuf,
+  ) -> Result<Self, AnyError> {
     let editor_config = Config::builder()
       .completion_type(CompletionType::List)
       .build();
@@ -389,25 +396,35 @@ impl ReplEditor {
       EventHandler::Conditional(Box::new(TabEventHandler)),
     );
 
-    ReplEditor {
+    let history_file_dir = history_file_path.parent().unwrap();
+    std::fs::create_dir_all(history_file_dir).with_context(|| {
+      format!(
+        "Unable to create directory for the history file: {}",
+        history_file_dir.display()
+      )
+    })?;
+
+    Ok(ReplEditor {
       inner: Arc::new(Mutex::new(editor)),
       history_file_path,
-    }
+      errored_on_history_save: Arc::new(AtomicBool::new(false)),
+    })
   }
 
   pub fn readline(&self) -> Result<String, ReadlineError> {
     self.inner.lock().readline("> ")
   }
 
-  pub fn add_history_entry(&self, entry: String) {
+  pub fn update_history(&self, entry: String) {
     self.inner.lock().add_history_entry(entry);
-  }
-
-  pub fn save_history(&self) -> Result<(), AnyError> {
-    std::fs::create_dir_all(self.history_file_path.parent().unwrap())?;
+    if let Err(e) = self.inner.lock().append_history(&self.history_file_path) {
+      if self.errored_on_history_save.load(Relaxed) {
+        return;
+      }
 
-    self.inner.lock().save_history(&self.history_file_path)?;
-    Ok(())
+      self.errored_on_history_save.store(true, Relaxed);
+      eprintln!("Unable to save history file: {}", e);
+    }
   }
 }
 
diff --git a/cli/tools/repl/mod.rs b/cli/tools/repl/mod.rs
index c8efd3d95..e37591583 100644
--- a/cli/tools/repl/mod.rs
+++ b/cli/tools/repl/mod.rs
@@ -89,7 +89,7 @@ pub async fn run(
   };
 
   let history_file_path = ps.dir.root.join("deno_history.txt");
-  let editor = ReplEditor::new(helper, history_file_path);
+  let editor = ReplEditor::new(helper, history_file_path)?;
 
   if let Some(eval_files) = maybe_eval_files {
     for eval_file in eval_files {
@@ -131,6 +131,7 @@ pub async fn run(
     match line {
       Ok(line) => {
         should_exit_on_interrupt = false;
+        editor.update_history(line.clone());
         let output = repl_session.evaluate_line_and_get_output(&line).await?;
 
         // We check for close and break here instead of making it a loop condition to get
@@ -140,8 +141,6 @@ pub async fn run(
         }
 
         println!("{}", output);
-
-        editor.add_history_entry(line);
       }
       Err(ReadlineError::Interrupted) => {
         if should_exit_on_interrupt {
@@ -161,7 +160,5 @@ pub async fn run(
     }
   }
 
-  editor.save_history()?;
-
   Ok(repl_session.worker.get_exit_code())
 }