diff --git a/cli/tools/repl/editor.rs b/cli/tools/repl/editor.rs
index 69fec9df06..73196d3f34 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);
-  }
+    if let Err(e) = self.inner.lock().append_history(&self.history_file_path) {
+      if self.errored_on_history_save.load(Relaxed) {
+        return;
+      }
 
-  pub fn save_history(&self) -> Result<(), AnyError> {
-    std::fs::create_dir_all(self.history_file_path.parent().unwrap())?;
-
-    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 a41fe61187..d4d8060f53 100644
--- a/cli/tools/repl/mod.rs
+++ b/cli/tools/repl/mod.rs
@@ -154,7 +154,7 @@ 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)?;
 
   println!("Deno {}", crate::version::deno());
   println!("exit using ctrl+d, ctrl+c, or close()");
@@ -169,35 +169,42 @@ pub async fn run(
     match line {
       Ok(line) => {
         should_exit_on_interrupt = false;
+        editor.update_history(line.clone());
 
-        if line == ".restart" {
-          println!("Started a new REPL session. Global scope has been reset.");
-          repl_session = create_repl_session(
-            ps,
-            module_url.clone(),
-            maybe_eval_files.clone(),
-            maybe_eval.clone(),
-          )
-          .await?;
-          continue;
-        } else if line == ".help" {
-          print_help();
-          continue;
-        } else if line == ".exit" {
-          break;
+        match &line {
+          ".restart" => {
+            println!(
+              "Started a new REPL session. Global scope has been reset."
+            );
+            repl_session = create_repl_session(
+              ps,
+              module_url.clone(),
+              maybe_eval_files.clone(),
+              maybe_eval.clone(),
+            )
+            .await?;
+            continue;
+          }
+          ".help" => {
+            print_help();
+            continue;
+          }
+          ".exit" => {
+            break;
+          }
+          line => {
+            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
+            // consistent behavior in when the user evaluates a call to close().
+            if repl_session.closing().await? {
+              break;
+            }
+
+            println!("{}", output);
+          }
         }
-
-        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
-        // consistent behavior in when the user evaluates a call to close().
-        if repl_session.closing().await? {
-          break;
-        }
-
-        println!("{}", output);
-
-        editor.add_history_entry(line);
       }
       Err(ReadlineError::Interrupted) => {
         if should_exit_on_interrupt {
@@ -217,7 +224,5 @@ pub async fn run(
     }
   }
 
-  editor.save_history()?;
-
   Ok(repl_session.worker.get_exit_code())
 }