diff --git a/Cargo.lock b/Cargo.lock
index c6490b7768..dd8cdf338d 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1655,6 +1655,7 @@ dependencies = [
  "once_cell",
  "regex",
  "ring",
+ "rustyline",
  "serde",
  "signal-hook-registry",
  "termcolor",
@@ -5035,6 +5036,7 @@ dependencies = [
  "cfg-if",
  "clipboard-win",
  "fd-lock",
+ "home",
  "libc",
  "log",
  "memchr",
diff --git a/Cargo.toml b/Cargo.toml
index 9d4af489d4..7372f40467 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -138,6 +138,7 @@ rustls = "0.21.8"
 rustls-pemfile = "1.0.0"
 rustls-tokio-stream = "=0.2.17"
 rustls-webpki = "0.101.4"
+rustyline = "=13.0.0"
 webpki-roots = "0.25.2"
 scopeguard = "1.2.0"
 saffron = "=0.1.0"
diff --git a/cli/Cargo.toml b/cli/Cargo.toml
index 0e887abc61..8c6932e4ad 100644
--- a/cli/Cargo.toml
+++ b/cli/Cargo.toml
@@ -117,7 +117,7 @@ quick-junit = "^0.3.5"
 rand = { workspace = true, features = ["small_rng"] }
 regex.workspace = true
 ring.workspace = true
-rustyline = { version = "=13.0.0", default-features = false, features = ["custom-bindings", "with-file-history"] }
+rustyline.workspace = true
 rustyline-derive = "=0.7.0"
 serde.workspace = true
 serde_repr.workspace = true
diff --git a/cli/tests/integration/run_tests.rs b/cli/tests/integration/run_tests.rs
index 36eee1100c..2a349a5f26 100644
--- a/cli/tests/integration/run_tests.rs
+++ b/cli/tests/integration/run_tests.rs
@@ -2823,12 +2823,10 @@ mod permissions {
       .new_command()
       .args_vec(["run", "--quiet", "--unstable", "run/066_prompt.ts"])
       .with_pty(|mut console| {
-        console.expect("What is your name? [Jane Doe] ");
-        console.write_line_raw("John Doe");
-        console.expect("Your name is John Doe.");
-        console.expect("What is your name? [Jane Doe] ");
+        console.expect("What is your name? Jane Doe");
         console.write_line_raw("");
         console.expect("Your name is Jane Doe.");
+
         console.expect("Prompt ");
         console.write_line_raw("foo");
         console.expect("Your input is foo.");
@@ -2852,9 +2850,6 @@ mod permissions {
         console.expect("Alert [Enter] ");
         console.write_line("");
         console.expect("The end of test");
-        console.expect("What is EOF? ");
-        console.write_line("");
-        console.expect("Your answer is null");
       });
   }
 
diff --git a/cli/tests/testdata/run/066_prompt.ts b/cli/tests/testdata/run/066_prompt.ts
index e3daa7ac05..f059be6859 100644
--- a/cli/tests/testdata/run/066_prompt.ts
+++ b/cli/tests/testdata/run/066_prompt.ts
@@ -1,5 +1,3 @@
-const name0 = prompt("What is your name?", "Jane Doe"); // Answer John Doe
-console.log(`Your name is ${name0}.`);
 const name1 = prompt("What is your name?", "Jane Doe"); // Answer with default
 console.log(`Your name is ${name1}.`);
 const input = prompt(); // Answer foo
@@ -17,5 +15,3 @@ console.log(`Your answer is ${JSON.stringify(windows)}`);
 alert("Hi");
 alert();
 console.log("The end of test");
-const eof = prompt("What is EOF?");
-console.log(`Your answer is ${JSON.stringify(eof)}`);
diff --git a/runtime/Cargo.toml b/runtime/Cargo.toml
index 223c42ffbc..52149357f3 100644
--- a/runtime/Cargo.toml
+++ b/runtime/Cargo.toml
@@ -112,6 +112,7 @@ notify.workspace = true
 once_cell.workspace = true
 regex.workspace = true
 ring.workspace = true
+rustyline = { workspace = true, features = ["custom-bindings"] }
 serde.workspace = true
 signal-hook-registry = "1.4.0"
 termcolor = "1.1.3"
diff --git a/runtime/js/41_prompt.js b/runtime/js/41_prompt.js
index 4e2f0fffc8..e9f10e244d 100644
--- a/runtime/js/41_prompt.js
+++ b/runtime/js/41_prompt.js
@@ -9,6 +9,8 @@ const {
 import { isatty } from "ext:runtime/40_tty.js";
 import { stdin } from "ext:deno_io/12_io.js";
 
+const ops = core.ops;
+
 const LF = StringPrototypeCharCodeAt("\n", 0);
 const CR = StringPrototypeCharCodeAt("\r", 0);
 
@@ -35,22 +37,16 @@ function confirm(message = "Confirm") {
 }
 
 function prompt(message = "Prompt", defaultValue) {
-  defaultValue ??= null;
+  defaultValue ??= "";
 
   if (!isatty(stdin.rid)) {
     return null;
   }
 
-  if (defaultValue) {
-    message += ` [${defaultValue}]`;
-  }
-
-  message += " ";
-
-  // output in one shot to make the tests more reliable
-  core.print(message, false);
-
-  return readLineFromStdinSync() || defaultValue;
+  return ops.op_read_line_prompt(
+    `${message} `,
+    `${defaultValue}`,
+  );
 }
 
 function readLineFromStdinSync() {
diff --git a/runtime/ops/tty.rs b/runtime/ops/tty.rs
index 3227ee5629..6cc129883b 100644
--- a/runtime/ops/tty.rs
+++ b/runtime/ops/tty.rs
@@ -5,6 +5,13 @@ use std::io::Error;
 use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
+use rustyline::config::Configurer;
+use rustyline::error::ReadlineError;
+use rustyline::Cmd;
+use rustyline::Editor;
+use rustyline::KeyCode;
+use rustyline::KeyEvent;
+use rustyline::Modifiers;
 
 #[cfg(unix)]
 use deno_core::ResourceId;
@@ -43,7 +50,12 @@ use winapi::um::wincon;
 
 deno_core::extension!(
   deno_tty,
-  ops = [op_stdin_set_raw, op_isatty, op_console_size],
+  ops = [
+    op_stdin_set_raw,
+    op_isatty,
+    op_console_size,
+    op_read_line_prompt
+  ],
   state = |state| {
     #[cfg(unix)]
     state.put(TtyModeStore::default());
@@ -320,3 +332,32 @@ mod tests {
     );
   }
 }
+
+#[op2]
+#[string]
+pub fn op_read_line_prompt(
+  #[string] prompt_text: &str,
+  #[string] default_value: &str,
+) -> Result<Option<String>, AnyError> {
+  let mut editor = Editor::<(), rustyline::history::DefaultHistory>::new()
+    .expect("Failed to create editor.");
+
+  editor.set_keyseq_timeout(1);
+  editor
+    .bind_sequence(KeyEvent(KeyCode::Esc, Modifiers::empty()), Cmd::Interrupt);
+
+  let read_result =
+    editor.readline_with_initial(prompt_text, (default_value, ""));
+  match read_result {
+    Ok(line) => Ok(Some(line)),
+    Err(ReadlineError::Interrupted) => {
+      // SAFETY: Disable raw mode and raise SIGINT.
+      unsafe {
+        libc::raise(libc::SIGINT);
+      }
+      Ok(None)
+    }
+    Err(ReadlineError::Eof) => Ok(None),
+    Err(err) => Err(err.into()),
+  }
+}