diff --git a/cli/file_watcher.rs b/cli/file_watcher.rs
index c7fff4632d..84b30dfd26 100644
--- a/cli/file_watcher.rs
+++ b/cli/file_watcher.rs
@@ -4,9 +4,7 @@ use crate::colors;
 use crate::fs_util::canonicalize_path;
 
 use deno_core::error::AnyError;
-use deno_core::futures::stream::{Stream, StreamExt};
 use deno_core::futures::Future;
-use deno_core::parking_lot::Mutex;
 use log::info;
 use notify::event::Event as NotifyEvent;
 use notify::event::EventKind;
@@ -15,57 +13,42 @@ use notify::Error as NotifyError;
 use notify::RecommendedWatcher;
 use notify::RecursiveMode;
 use notify::Watcher;
-use pin_project::pin_project;
 use std::collections::HashSet;
 use std::path::PathBuf;
-use std::pin::Pin;
 use std::sync::Arc;
-use std::task::Context;
-use std::task::Poll;
 use std::time::Duration;
-use tokio::pin;
 use tokio::select;
+use tokio::sync::mpsc;
 use tokio::time::sleep;
-use tokio::time::Instant;
-use tokio::time::Sleep;
 
 const DEBOUNCE_INTERVAL: Duration = Duration::from_millis(200);
 
-#[pin_project(project = DebounceProjection)]
-struct Debounce {
-  #[pin]
-  timer: Sleep,
-  changed_paths: Arc<Mutex<HashSet<PathBuf>>>,
+struct DebouncedReceiver {
+  receiver: mpsc::UnboundedReceiver<Vec<PathBuf>>,
 }
 
-impl Debounce {
-  fn new() -> Self {
-    Self {
-      timer: sleep(DEBOUNCE_INTERVAL),
-      changed_paths: Arc::new(Mutex::new(HashSet::new())),
-    }
+impl DebouncedReceiver {
+  fn new_with_sender() -> (Arc<mpsc::UnboundedSender<Vec<PathBuf>>>, Self) {
+    let (sender, receiver) = mpsc::unbounded_channel();
+    (Arc::new(sender), Self { receiver })
   }
-}
 
-impl Stream for Debounce {
-  type Item = Vec<PathBuf>;
-
-  /// Note that this never returns `Poll::Ready(None)`, which means that the
-  /// file watcher will be alive until the Deno process is terminated.
-  fn poll_next(
-    self: Pin<&mut Self>,
-    cx: &mut Context,
-  ) -> Poll<Option<Self::Item>> {
-    let mut changed_paths = self.changed_paths.lock();
-    if changed_paths.len() > 0 {
-      Poll::Ready(Some(changed_paths.drain().collect()))
-    } else {
-      drop(changed_paths);
-      let mut timer = self.project().timer;
-      if timer.as_mut().poll(cx).is_ready() {
-        timer.reset(Instant::now() + DEBOUNCE_INTERVAL);
+  async fn recv(&mut self) -> Option<Vec<PathBuf>> {
+    let mut received_items = self
+      .receiver
+      .recv()
+      .await?
+      .into_iter()
+      .collect::<HashSet<_>>(); // prevent duplicates
+    loop {
+      tokio::select! {
+        items = self.receiver.recv() => {
+          received_items.extend(items?);
+        }
+        _ = sleep(DEBOUNCE_INTERVAL) => {
+          return Some(received_items.into_iter().collect());
+        }
       }
-      Poll::Pending
     }
   }
 }
@@ -91,14 +74,14 @@ pub enum ResolutionResult<T> {
 
 async fn next_restart<R, T, F>(
   resolver: &mut R,
-  debounce: &mut Pin<&mut Debounce>,
+  debounced_receiver: &mut DebouncedReceiver,
 ) -> (Vec<PathBuf>, Result<T, AnyError>)
 where
   R: FnMut(Option<Vec<PathBuf>>) -> F,
   F: Future<Output = ResolutionResult<T>>,
 {
   loop {
-    let changed = debounce.next().await;
+    let changed = debounced_receiver.recv().await;
     match resolver(changed).await {
       ResolutionResult::Ignore => {
         log::debug!("File change ignored")
@@ -140,8 +123,7 @@ where
   F1: Future<Output = ResolutionResult<T>>,
   F2: Future<Output = Result<(), AnyError>>,
 {
-  let debounce = Debounce::new();
-  pin!(debounce);
+  let (sender, mut receiver) = DebouncedReceiver::new_with_sender();
 
   // Store previous data. If module resolution fails at some point, the watcher will try to
   // continue watching files using these data.
@@ -161,7 +143,7 @@ where
         colors::intense_blue("Watcher"),
       );
 
-      let (paths, result) = next_restart(&mut resolver, &mut debounce).await;
+      let (paths, result) = next_restart(&mut resolver, &mut receiver).await;
       paths_to_watch = paths;
       resolution_result = result;
     }
@@ -175,13 +157,13 @@ where
   };
 
   loop {
-    let watcher = new_watcher(&paths_to_watch, &debounce)?;
+    let watcher = new_watcher(&paths_to_watch, sender.clone())?;
 
     match resolution_result {
       Ok(operation_arg) => {
         let fut = error_handler(operation(operation_arg));
         select! {
-          (paths, result) = next_restart(&mut resolver, &mut debounce) => {
+          (paths, result) = next_restart(&mut resolver, &mut receiver) => {
             if result.is_ok() {
               paths_to_watch = paths;
             }
@@ -207,7 +189,7 @@ where
       }
     }
 
-    let (paths, result) = next_restart(&mut resolver, &mut debounce).await;
+    let (paths, result) = next_restart(&mut resolver, &mut receiver).await;
     if result.is_ok() {
       paths_to_watch = paths;
     }
@@ -219,10 +201,8 @@ where
 
 fn new_watcher(
   paths: &[PathBuf],
-  debounce: &Debounce,
+  sender: Arc<mpsc::UnboundedSender<Vec<PathBuf>>>,
 ) -> Result<RecommendedWatcher, AnyError> {
-  let changed_paths = Arc::clone(&debounce.changed_paths);
-
   let mut watcher: RecommendedWatcher =
     Watcher::new(move |res: Result<NotifyEvent, NotifyError>| {
       if let Ok(event) = res {
@@ -233,9 +213,9 @@ fn new_watcher(
           let paths = event
             .paths
             .iter()
-            .filter_map(|path| canonicalize_path(path).ok());
-          let mut changed_paths = changed_paths.lock();
-          changed_paths.extend(paths);
+            .filter_map(|path| canonicalize_path(path).ok())
+            .collect();
+          sender.send(paths).unwrap();
         }
       }
     })?;
diff --git a/cli/ops/runtime_compiler.rs b/cli/ops/runtime_compiler.rs
index d79a5fe31f..af99f12caa 100644
--- a/cli/ops/runtime_compiler.rs
+++ b/cli/ops/runtime_compiler.rs
@@ -166,7 +166,9 @@ async fn op_emit(
     args.import_map_path
   {
     let import_map_specifier = resolve_url_or_path(&import_map_str)
-      .context(format!("Bad URL (\"{}\") for import map.", import_map_str))?;
+      .with_context(|| {
+        format!("Bad URL (\"{}\") for import map.", import_map_str)
+      })?;
     let import_map = if let Some(value) = args.import_map {
       ImportMap::from_json(import_map_specifier.as_str(), &value.to_string())?
     } else {
diff --git a/cli/tests/integration/watcher_tests.rs b/cli/tests/integration/watcher_tests.rs
index 42ca4b520e..c9a5632c04 100644
--- a/cli/tests/integration/watcher_tests.rs
+++ b/cli/tests/integration/watcher_tests.rs
@@ -18,7 +18,7 @@ macro_rules! assert_contains {
 // Helper function to skip watcher output that contains "Restarting"
 // phrase.
 fn skip_restarting_line(
-  mut stderr_lines: impl Iterator<Item = String>,
+  stderr_lines: &mut impl Iterator<Item = String>,
 ) -> String {
   loop {
     let msg = stderr_lines.next().unwrap();
@@ -69,10 +69,18 @@ fn child_lines(
 ) -> (impl Iterator<Item = String>, impl Iterator<Item = String>) {
   let stdout_lines = std::io::BufReader::new(child.stdout.take().unwrap())
     .lines()
-    .map(|r| r.unwrap());
+    .map(|r| {
+      let line = r.unwrap();
+      eprintln!("STDOUT: {}", line);
+      line
+    });
   let stderr_lines = std::io::BufReader::new(child.stderr.take().unwrap())
     .lines()
-    .map(|r| r.unwrap());
+    .map(|r| {
+      let line = r.unwrap();
+      eprintln!("STERR: {}", line);
+      line
+    });
   (stdout_lines, stderr_lines)
 }
 
@@ -106,13 +114,7 @@ fn lint_watch_test() {
     .stderr(std::process::Stdio::piped())
     .spawn()
     .expect("Failed to spawn script");
-  let mut stderr = child.stderr.as_mut().unwrap();
-  let mut stderr_lines = std::io::BufReader::new(&mut stderr)
-    .lines()
-    .map(|r| r.unwrap());
-
-  // TODO(lucacasonato): remove this timeout. It seems to be needed on Linux.
-  std::thread::sleep(std::time::Duration::from_secs(1));
+  let (_stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
   let mut output = read_all_lints(&mut stderr_lines);
   let expected = std::fs::read_to_string(badly_linted_output).unwrap();
@@ -130,7 +132,6 @@ fn lint_watch_test() {
   // Change content of the file again to be badly-linted1
   std::fs::copy(&badly_linted_fixed2, &badly_linted)
     .expect("Failed to copy file");
-  std::thread::sleep(std::time::Duration::from_secs(1));
 
   output = read_all_lints(&mut stderr_lines);
   let expected = std::fs::read_to_string(badly_linted_fixed2_output).unwrap();
@@ -172,13 +173,7 @@ fn lint_watch_without_args_test() {
     .stderr(std::process::Stdio::piped())
     .spawn()
     .expect("Failed to spawn script");
-  let mut stderr = child.stderr.as_mut().unwrap();
-  let mut stderr_lines = std::io::BufReader::new(&mut stderr)
-    .lines()
-    .map(|r| r.unwrap());
-
-  // TODO(lucacasonato): remove this timeout. It seems to be needed on Linux.
-  std::thread::sleep(std::time::Duration::from_secs(1));
+  let (_stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
   let mut output = read_all_lints(&mut stderr_lines);
   let expected = std::fs::read_to_string(badly_linted_output).unwrap();
@@ -187,7 +182,6 @@ fn lint_watch_without_args_test() {
   // Change content of the file again to be badly-linted1
   std::fs::copy(&badly_linted_fixed1, &badly_linted)
     .expect("Failed to copy file");
-  std::thread::sleep(std::time::Duration::from_secs(1));
 
   output = read_all_lints(&mut stderr_lines);
   let expected = std::fs::read_to_string(badly_linted_fixed1_output).unwrap();
@@ -236,18 +230,12 @@ fn lint_all_files_on_each_change_test() {
     .stderr(std::process::Stdio::piped())
     .spawn()
     .expect("Failed to spawn script");
-  let mut stderr = child.stderr.as_mut().unwrap();
-  let mut stderr_lines = std::io::BufReader::new(&mut stderr)
-    .lines()
-    .map(|r| r.unwrap());
-
-  std::thread::sleep(std::time::Duration::from_secs(1));
+  let (_stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
   assert_contains!(read_line("Checked", &mut stderr_lines), "Checked 2 files");
 
   std::fs::copy(&badly_linted_fixed2, &badly_linted_2)
     .expect("Failed to copy file");
-  std::thread::sleep(std::time::Duration::from_secs(1));
 
   assert_contains!(read_line("Checked", &mut stderr_lines), "Checked 2 files");
 
@@ -276,12 +264,13 @@ fn fmt_watch_test() {
     .stderr(std::process::Stdio::piped())
     .spawn()
     .unwrap();
-  let (_stdout_lines, stderr_lines) = child_lines(&mut child);
+  let (_stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
-  // TODO(lucacasonato): remove this timeout. It seems to be needed on Linux.
-  std::thread::sleep(std::time::Duration::from_secs(1));
-
-  assert!(skip_restarting_line(stderr_lines).contains("badly_formatted.js"));
+  assert_contains!(
+    skip_restarting_line(&mut stderr_lines),
+    "badly_formatted.js"
+  );
+  assert_contains!(read_line("Checked", &mut stderr_lines), "Checked 1 file");
 
   let expected = std::fs::read_to_string(fixed.clone()).unwrap();
   let actual = std::fs::read_to_string(badly_formatted.clone()).unwrap();
@@ -289,7 +278,12 @@ fn fmt_watch_test() {
 
   // Change content of the file again to be badly formatted
   std::fs::copy(&badly_formatted_original, &badly_formatted).unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
+  assert_contains!(
+    skip_restarting_line(&mut stderr_lines),
+    "badly_formatted.js"
+  );
+  assert_contains!(read_line("Checked", &mut stderr_lines), "Checked 1 file");
 
   // Check if file has been automatically formatted by watcher
   let expected = std::fs::read_to_string(fixed).unwrap();
@@ -316,12 +310,13 @@ fn fmt_watch_without_args_test() {
     .stderr(std::process::Stdio::piped())
     .spawn()
     .unwrap();
-  let (_stdout_lines, stderr_lines) = child_lines(&mut child);
+  let (_stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
-  // TODO(lucacasonato): remove this timeout. It seems to be needed on Linux.
-  std::thread::sleep(std::time::Duration::from_secs(1));
-
-  assert!(skip_restarting_line(stderr_lines).contains("badly_formatted.js"));
+  assert_contains!(
+    skip_restarting_line(&mut stderr_lines),
+    "badly_formatted.js"
+  );
+  assert_contains!(read_line("Checked", &mut stderr_lines), "Checked 1 file");
 
   let expected = std::fs::read_to_string(fixed.clone()).unwrap();
   let actual = std::fs::read_to_string(badly_formatted.clone()).unwrap();
@@ -329,7 +324,11 @@ fn fmt_watch_without_args_test() {
 
   // Change content of the file again to be badly formatted
   std::fs::copy(&badly_formatted_original, &badly_formatted).unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+  assert_contains!(
+    skip_restarting_line(&mut stderr_lines),
+    "badly_formatted.js"
+  );
+  assert_contains!(read_line("Checked", &mut stderr_lines), "Checked 1 file");
 
   // Check if file has been automatically formatted by watcher
   let expected = std::fs::read_to_string(fixed).unwrap();
@@ -361,9 +360,6 @@ fn fmt_check_all_files_on_each_change_test() {
     .unwrap();
   let (_stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
-  // TODO(lucacasonato): remove this timeout. It seems to be needed on Linux.
-  std::thread::sleep(std::time::Duration::from_secs(1));
-
   assert_contains!(
     read_line("error", &mut stderr_lines),
     "Found 2 not formatted files in 2 files"
@@ -372,8 +368,6 @@ fn fmt_check_all_files_on_each_change_test() {
   // Change content of the file again to be badly formatted
   std::fs::copy(&badly_formatted_original, &badly_formatted_1).unwrap();
 
-  std::thread::sleep(std::time::Duration::from_secs(1));
-
   assert_contains!(
     read_line("error", &mut stderr_lines),
     "Found 2 not formatted files in 2 files"
@@ -407,7 +401,6 @@ fn bundle_js_watch() {
 
   let (_stdout_lines, mut stderr_lines) = child_lines(&mut deno);
 
-  std::thread::sleep(std::time::Duration::from_secs(1));
   assert_contains!(stderr_lines.next().unwrap(), "Check");
   assert_contains!(stderr_lines.next().unwrap(), "file_to_watch.js");
   assert_contains!(stderr_lines.next().unwrap(), "mod6.bundle.js");
@@ -416,7 +409,7 @@ fn bundle_js_watch() {
   wait_for("Bundle finished", &mut stderr_lines);
 
   write(&file_to_watch, "console.log('Hello world2');").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Check");
   assert_contains!(stderr_lines.next().unwrap(), "File change detected!");
   assert_contains!(stderr_lines.next().unwrap(), "file_to_watch.js");
@@ -427,7 +420,7 @@ fn bundle_js_watch() {
 
   // Confirm that the watcher keeps on working even if the file is updated and has invalid syntax
   write(&file_to_watch, "syntax error ^^").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "File change detected!");
   assert_contains!(stderr_lines.next().unwrap(), "error: ");
   wait_for("Bundle failed", &mut stderr_lines);
@@ -456,7 +449,6 @@ fn bundle_watch_not_exit() {
     .unwrap();
   let (_stdout_lines, mut stderr_lines) = child_lines(&mut deno);
 
-  std::thread::sleep(std::time::Duration::from_secs(1));
   assert_contains!(stderr_lines.next().unwrap(), "error:");
   assert_contains!(stderr_lines.next().unwrap(), "Bundle failed");
   // the target file hasn't been created yet
@@ -464,12 +456,14 @@ fn bundle_watch_not_exit() {
 
   // Make sure the watcher actually restarts and works fine with the proper syntax
   write(&file_to_watch, "console.log(42);").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Check");
   assert_contains!(stderr_lines.next().unwrap(), "File change detected!");
   assert_contains!(stderr_lines.next().unwrap(), "file_to_watch.js");
   assert_contains!(stderr_lines.next().unwrap(), "target.js");
+
   wait_for("Bundle finished", &mut stderr_lines);
+
   // bundled file is created
   assert!(target_file.is_file());
   check_alive_then_kill(deno);
@@ -497,13 +491,8 @@ fn run_watch() {
   assert_contains!(stdout_lines.next().unwrap(), "Hello world");
   wait_for("Process finished", &mut stderr_lines);
 
-  // TODO(lucacasonato): remove this timeout. It seems to be needed on Linux.
-  std::thread::sleep(std::time::Duration::from_secs(1));
-
   // Change content of the file
   write(&file_to_watch, "console.log('Hello world2');").unwrap();
-  // Events from the file watcher is "debounced", so we need to wait for the next execution to start
-  std::thread::sleep(std::time::Duration::from_secs(1));
 
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stdout_lines.next().unwrap(), "Hello world2");
@@ -517,21 +506,21 @@ fn run_watch() {
     "import { foo } from './another_file.js'; console.log(foo);",
   )
   .unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stdout_lines.next().unwrap(), '0');
   wait_for("Process finished", &mut stderr_lines);
 
   // Confirm that restarting occurs when a new file is updated
   write(&another_file, "export const foo = 42;").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stdout_lines.next().unwrap(), "42");
   wait_for("Process finished", &mut stderr_lines);
 
   // Confirm that the watcher keeps on working even if the file is updated and has invalid syntax
   write(&file_to_watch, "syntax error ^^").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stderr_lines.next().unwrap(), "error:");
   wait_for("Process failed", &mut stderr_lines);
@@ -542,21 +531,21 @@ fn run_watch() {
     "import { foo } from './another_file.js'; console.log(foo);",
   )
   .unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stdout_lines.next().unwrap(), "42");
   wait_for("Process finished", &mut stderr_lines);
 
   // Update the content of the imported file with invalid syntax
   write(&another_file, "syntax error ^^").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stderr_lines.next().unwrap(), "error:");
   wait_for("Process failed", &mut stderr_lines);
 
   // Modify the imported file and make sure that restarting occurs
   write(&another_file, "export const foo = 'modified!';").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stdout_lines.next().unwrap(), "modified!");
   wait_for("Process finished", &mut stderr_lines);
@@ -613,9 +602,6 @@ fn run_watch_load_unload_events() {
   )
   .unwrap();
 
-  // Events from the file watcher is "debounced", so we need to wait for the next execution to start
-  std::thread::sleep(std::time::Duration::from_secs(1));
-
   // Wait for the restart
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
 
@@ -650,13 +636,12 @@ fn run_watch_not_exit() {
     .unwrap();
   let (mut stdout_lines, mut stderr_lines) = child_lines(&mut child);
 
-  std::thread::sleep(std::time::Duration::from_secs(1));
   assert_contains!(stderr_lines.next().unwrap(), "error:");
   assert_contains!(stderr_lines.next().unwrap(), "Process failed");
 
   // Make sure the watcher actually restarts and works fine with the proper syntax
   write(&file_to_watch, "console.log(42);").unwrap();
-  std::thread::sleep(std::time::Duration::from_secs(1));
+
   assert_contains!(stderr_lines.next().unwrap(), "Restarting");
   assert_contains!(stdout_lines.next().unwrap(), "42");
   wait_for("Process finished", &mut stderr_lines);
@@ -905,6 +890,6 @@ fn test_watch_doc() {
 
   // We only need to scan for a Check file://.../foo.ts$3-6 line that
   // corresponds to the documentation block being type-checked.
-  assert_contains!(skip_restarting_line(stderr_lines), "foo.ts$3-6");
+  assert_contains!(skip_restarting_line(&mut stderr_lines), "foo.ts$3-6");
   check_alive_then_kill(child);
 }
diff --git a/cli/tools/fmt.rs b/cli/tools/fmt.rs
index 2149552cd6..9172421b51 100644
--- a/cli/tools/fmt.rs
+++ b/cli/tools/fmt.rs
@@ -19,6 +19,7 @@ use crate::fs_util::specifier_to_file_path;
 use crate::fs_util::{collect_files, get_extension, is_supported_ext_fmt};
 use crate::text_encoding;
 use deno_ast::ParsedSource;
+use deno_core::anyhow::Context;
 use deno_core::error::generic_error;
 use deno_core::error::AnyError;
 use deno_core::futures;
@@ -525,7 +526,8 @@ struct FileContents {
 }
 
 fn read_file_contents(file_path: &Path) -> Result<FileContents, AnyError> {
-  let file_bytes = fs::read(&file_path)?;
+  let file_bytes = fs::read(&file_path)
+    .with_context(|| format!("Error reading {}", file_path.display()))?;
   let charset = text_encoding::detect_charset(&file_bytes);
   let file_text = text_encoding::convert_to_utf8(&file_bytes, charset)?;
   let had_bom = file_text.starts_with(text_encoding::BOM_CHAR);