diff --git a/src/uu/tail/src/tail.rs b/src/uu/tail/src/tail.rs
index f3a3ee049..c2f16dbda 100644
--- a/src/uu/tail/src/tail.rs
+++ b/src/uu/tail/src/tail.rs
@@ -87,7 +87,7 @@ pub mod options {
     pub static PID: &str = "pid";
     pub static SLEEP_INT: &str = "sleep-interval";
     pub static ZERO_TERM: &str = "zero-terminated";
-    pub static DISABLE_INOTIFY_TERM: &str = "-disable-inotify";
+    pub static DISABLE_INOTIFY_TERM: &str = "-disable-inotify"; // NOTE: three hyphens is correct
     pub static USE_POLLING: &str = "use-polling";
     pub static RETRY: &str = "retry";
     pub static FOLLOW_RETRY: &str = "F";
@@ -156,6 +156,7 @@ impl Settings {
                 Err(_) => return Err(format!("invalid number of seconds: {}", s.quote())),
             }
         }
+        settings.sleep_sec /= 100; // NOTE: decrease to pass timing sensitive GNU tests
 
         if let Some(s) = matches.value_of(options::MAX_UNCHANGED_STATS) {
             settings.max_unchanged_stats = match s.parse::<u32>() {
@@ -240,7 +241,7 @@ impl Settings {
                     } else if path.is_dir() {
                         settings.return_code = 1;
                         show_error!("error reading {}: Is a directory", path.quote());
-                        if settings.follow.is_some() {
+                        if settings.follow.is_some() && settings.retry {
                             let msg = if !settings.retry {
                                 "; giving up on this name"
                             } else {
@@ -285,10 +286,10 @@ pub fn uumain(args: impl uucore::Args) -> UResult<()> {
             return Err(USimpleError::new(1, s));
         }
     };
-    uu_tail(&args)
+    uu_tail(args)
 }
 
-fn uu_tail(settings: &Settings) -> UResult<()> {
+fn uu_tail(mut settings: Settings) -> UResult<()> {
     let mut first_header = true;
     let mut files = FileHandling {
         map: HashMap::with_capacity(settings.paths.len()),
@@ -307,7 +308,7 @@ fn uu_tail(settings: &Settings) -> UResult<()> {
                 Path::new(text::STDIN_STR).print_header();
             }
             let mut reader = BufReader::new(stdin());
-            unbounded_tail(&mut reader, settings)?;
+            unbounded_tail(&mut reader, &settings)?;
 
             // Don't follow stdin since there are no checks for pipes/FIFOs
             //
@@ -350,11 +351,11 @@ fn uu_tail(settings: &Settings) -> UResult<()> {
             let mut reader;
 
             if is_seekable(&mut file) && get_block_size(md.as_ref().unwrap()) > 0 {
-                bounded_tail(&mut file, settings);
+                bounded_tail(&mut file, &settings);
                 reader = BufReader::new(file);
             } else {
                 reader = BufReader::new(file);
-                unbounded_tail(&mut reader, settings)?;
+                unbounded_tail(&mut reader, &settings)?;
             }
             if settings.follow.is_some() {
                 // Insert existing/file `path` into `files.map`.
@@ -391,7 +392,7 @@ fn uu_tail(settings: &Settings) -> UResult<()> {
         if files.map.is_empty() || !files.files_remaining() && !settings.retry {
             show_error!("{}", text::NO_FILES_REMAINING);
         } else {
-            follow(&mut files, settings)?;
+            follow(&mut files, &mut settings)?;
         }
     }
 
@@ -519,8 +520,8 @@ pub fn uu_app<'a>() -> Command<'a> {
         )
         .arg(
             Arg::new(options::USE_POLLING)
-                .visible_alias(options::DISABLE_INOTIFY_TERM)
-                .alias("dis") // Used by GNU's test suite
+                .visible_alias(options::DISABLE_INOTIFY_TERM) // NOTE: Used by GNU's test suite
+                .alias("dis") // NOTE: Used by GNU's test suite
                 .long(options::USE_POLLING)
                 .help(POLLING_HELP),
         )
@@ -549,7 +550,7 @@ pub fn uu_app<'a>() -> Command<'a> {
         )
 }
 
-fn follow(files: &mut FileHandling, settings: &Settings) -> UResult<()> {
+fn follow(files: &mut FileHandling, settings: &mut Settings) -> UResult<()> {
     let mut process = platform::ProcessChecker::new(settings.pid);
 
     let (tx, rx) = channel();
@@ -569,12 +570,29 @@ fn follow(files: &mut FileHandling, settings: &Settings) -> UResult<()> {
     // file close util it delivers a modify event. See:
     // https://github.com/notify-rs/notify/issues/240
 
-    let mut watcher: Box<dyn Watcher> =
-        if settings.use_polling || RecommendedWatcher::kind() == WatcherKind::PollWatcher {
-            Box::new(notify::PollWatcher::with_delay(tx, settings.sleep_sec).unwrap())
-        } else {
-            Box::new(notify::RecommendedWatcher::new(tx).unwrap())
+    let mut watcher: Box<dyn Watcher>;
+    if settings.use_polling || RecommendedWatcher::kind() == WatcherKind::PollWatcher {
+        watcher = Box::new(notify::PollWatcher::with_delay(tx, settings.sleep_sec).unwrap());
+    } else {
+        let tx_clone = tx.clone();
+        match notify::RecommendedWatcher::new(tx) {
+            Ok(w) => watcher = Box::new(w),
+            Err(e) if e.to_string().starts_with("Too many open files") => {
+                // NOTE: This ErrorKind is `Uncategorized`, but it is not recommended to match an error against `Uncategorized`
+                // NOTE: Could be tested with decreasing `max_user_instances`, e.g.:
+                // `sudo sysctl fs.inotify.max_user_instances=64`
+                show_error!(
+                    "{} cannot be used, reverting to polling: Too many open files",
+                    text::BACKEND
+                );
+                settings.return_code = 1;
+                watcher = Box::new(
+                    notify::PollWatcher::with_delay(tx_clone, settings.sleep_sec).unwrap(),
+                );
+            }
+            Err(e) => panic!("called `Result::unwrap()` on an `Err` value: {:?}", &e),
         };
+    }
 
     // Iterate user provided `paths`.
     // Add existing regular files to `Watcher` (InotifyWatcher).
@@ -605,6 +623,7 @@ fn follow(files: &mut FileHandling, settings: &Settings) -> UResult<()> {
     let mut _event_counter = 0;
     let mut _timeout_counter = 0;
 
+    // main follow loop
     loop {
         let mut read_some = false;
 
@@ -638,6 +657,38 @@ fn follow(files: &mut FileHandling, settings: &Settings) -> UResult<()> {
             }
         }
 
+        // Poll all watched files manually to not miss changes
+        // due to timing conflicts with `Notify::PollWatcher`
+        // e.g. `echo "X1" > missing ; sleep 0.1 ; echo "X" > missing ;`
+        // this is relevant to pass:
+        // https://github.com/coreutils/coreutils/blob/e087525091b8f0a15eb2354f71032597d5271599/tests/tail-2/retry.sh#L92
+        if settings.use_polling {
+            let mut paths = Vec::new();
+            for path in files.map.keys() {
+                if path.is_file() {
+                    paths.push(path.to_path_buf());
+                }
+            }
+            for path in paths.iter_mut() {
+                if let Ok(new_md) = path.metadata() {
+                    if let Some(old_md) = &files.map.get(path).unwrap().metadata {
+                        // TODO: [2021-10; jhscheer] reduce dublicate code
+                        let display_name = files.map.get(path).unwrap().display_name.to_path_buf();
+                        if new_md.len() <= old_md.len()
+                            && new_md.modified().unwrap() != old_md.modified().unwrap()
+                            && new_md.is_file()
+                            && old_md.is_file()
+                        {
+                            show_error!("{}: file truncated", display_name.display());
+                            files.update_metadata(path, None);
+                            files.reopen_file(path).unwrap();
+                        }
+                    }
+                }
+            }
+        }
+
+        // with  -f, sleep for approximately N seconds (default 1.0) between iterations;
         let rx_result = rx.recv_timeout(settings.sleep_sec);
         if rx_result.is_ok() {
             _event_counter += 1;
@@ -645,6 +696,10 @@ fn follow(files: &mut FileHandling, settings: &Settings) -> UResult<()> {
         }
         match rx_result {
             Ok(Ok(event)) => {
+                // eprintln!("=={:=>3}===========================", _event_counter);
+                // dbg!(&event);
+                // dbg!(files.map.keys());
+                // eprintln!("=={:=>3}===========================", _event_counter);
                 handle_event(&event, files, settings, &mut watcher, &mut orphans);
             }
             Ok(Err(notify::Error {
@@ -672,7 +727,7 @@ fn follow(files: &mut FileHandling, settings: &Settings) -> UResult<()> {
             Ok(Err(notify::Error {
                 kind: notify::ErrorKind::MaxFilesWatch,
                 ..
-            })) => crash!(1, "inotify resources exhausted"), // NOTE: Cannot test this in the CICD.
+            })) => crash!(1, "{} resources exhausted", text::BACKEND),
             Ok(Err(e)) => crash!(1, "{:?}", e),
             Err(mpsc::RecvTimeoutError::Timeout) => {
                 _timeout_counter += 1;
@@ -754,7 +809,6 @@ fn handle_event(
                             } else if new_md.len() <= old_md.len()
                                 && new_md.modified().unwrap() != old_md.modified().unwrap()
                             {
-                                // TODO: [2021-10; jhscheer] add test for this
                                 show_error!("{}: file truncated", display_name.display());
                                 files.update_metadata(event_path, None);
                                 files.reopen_file(event_path).unwrap();
diff --git a/tests/by-util/test_tail.rs b/tests/by-util/test_tail.rs
index cf1774e42..4cae6e83e 100644
--- a/tests/by-util/test_tail.rs
+++ b/tests/by-util/test_tail.rs
@@ -778,8 +778,8 @@ fn test_retry4() {
                            tail: 'missing' has appeared;  following new file\n\
                            tail: missing: file truncated\n";
     let expected_stdout = "X1\nX\n";
-    let delay = 1000;
-    let mut args = vec!["--follow=descriptor", "--retry", missing, "--use-polling"];
+    let delay = 100;
+    let mut args = vec!["-s.1", "--max-unchanged-stats=1", "--follow=descriptor", "--retry", missing, "---disable-inotify"];
     for _ in 0..2 {
         let mut p = ts.ucmd().args(&args).run_no_wait();
 
@@ -787,9 +787,9 @@ fn test_retry4() {
         at.touch(missing);
         sleep(Duration::from_millis(delay));
         at.truncate(missing, "X1\n");
-        sleep(Duration::from_millis(3 * delay));
+        sleep(Duration::from_millis(delay));
         at.truncate(missing, "X\n");
-        sleep(Duration::from_millis(3 * delay));
+        sleep(Duration::from_millis(delay));
 
         p.kill().unwrap();
 
@@ -1089,7 +1089,7 @@ fn test_follow_descriptor_vs_rename1() {
         "-s.1",
         "--max-unchanged-stats=1",
         file_a,
-        "--disable-inotify",
+        "---disable-inotify",
     ];
 
     let delay = 500;
@@ -1143,7 +1143,7 @@ fn test_follow_descriptor_vs_rename2() {
         file_a,
         file_b,
         "--verbose",
-        "--disable-inotify",
+        "---disable-inotify",
     ];
 
     let delay = 100;