diff --git a/src/shell/commands/head.rs b/src/shell/commands/head.rs
index acfa7c0..cd84cde 100644
--- a/src/shell/commands/head.rs
+++ b/src/shell/commands/head.rs
@@ -81,47 +81,147 @@ fn copy_lines<F: FnMut(&mut [u8]) -> Result<usize>>(
   Ok(ExecuteResult::from_exit_code(0))
 }
 
+fn copy_all_but_last_lines<F: FnMut(&mut [u8]) -> Result<usize>>(
+  writer: &mut ShellPipeWriter,
+  skip_last: u64,
+  kill_signal: &KillSignal,
+  mut read: F,
+) -> Result<ExecuteResult> {
+  // read all content first
+  let mut content = Vec::new();
+  let mut buffer = vec![0; 512];
+  loop {
+    if let Some(exit_code) = kill_signal.aborted_code() {
+      return Ok(ExecuteResult::from_exit_code(exit_code));
+    }
+    let read_bytes = read(&mut buffer)?;
+    if read_bytes == 0 {
+      break;
+    }
+    content.extend_from_slice(&buffer[..read_bytes]);
+  }
+
+  // count total lines
+  let total_lines = content.iter().filter(|&&b| b == b'\n').count() as u64;
+
+  // output all but the last N lines
+  if total_lines <= skip_last {
+    return Ok(ExecuteResult::from_exit_code(0));
+  }
+  let lines_to_print = total_lines - skip_last;
+
+  let mut line_count = 0u64;
+  let mut start = 0;
+  for (i, &b) in content.iter().enumerate() {
+    if let Some(exit_code) = kill_signal.aborted_code() {
+      return Ok(ExecuteResult::from_exit_code(exit_code));
+    }
+    if b == b'\n' {
+      line_count += 1;
+      if line_count <= lines_to_print {
+        writer.write_all(&content[start..=i])?;
+      }
+      start = i + 1;
+      if line_count >= lines_to_print {
+        break;
+      }
+    }
+  }
+
+  Ok(ExecuteResult::from_exit_code(0))
+}
+
 fn execute_head(mut context: ShellCommandContext) -> Result<ExecuteResult> {
   let flags = parse_args(&context.args)?;
-  if flags.path == "-" {
-    copy_lines(
-      &mut context.stdout,
-      flags.lines,
-      context.state.kill_signal(),
-      |buf| context.stdin.read(buf),
-      512,
-    )
-  } else {
-    let path = flags.path;
-    match File::open(context.state.cwd().join(path)) {
-      Ok(mut file) => copy_lines(
-        &mut context.stdout,
-        flags.lines,
-        context.state.kill_signal(),
-        |buf| file.read(buf).map_err(Into::into),
-        512,
-      ),
-      Err(err) => {
-        context.stderr.write_line(&format!(
-          "head: {}: {}",
-          path.to_string_lossy(),
-          err
-        ))?;
-        Ok(ExecuteResult::from_exit_code(1))
+  match flags.lines {
+    LineCount::First(max_lines) => {
+      if flags.path == "-" {
+        copy_lines(
+          &mut context.stdout,
+          max_lines,
+          context.state.kill_signal(),
+          |buf| context.stdin.read(buf),
+          512,
+        )
+      } else {
+        let path = flags.path;
+        match File::open(context.state.cwd().join(path)) {
+          Ok(mut file) => copy_lines(
+            &mut context.stdout,
+            max_lines,
+            context.state.kill_signal(),
+            |buf| file.read(buf).map_err(Into::into),
+            512,
+          ),
+          Err(err) => {
+            context.stderr.write_line(&format!(
+              "head: {}: {}",
+              path.to_string_lossy(),
+              err
+            ))?;
+            Ok(ExecuteResult::from_exit_code(1))
+          }
+        }
+      }
+    }
+    LineCount::AllButLast(skip_last) => {
+      if flags.path == "-" {
+        copy_all_but_last_lines(
+          &mut context.stdout,
+          skip_last,
+          context.state.kill_signal(),
+          |buf| context.stdin.read(buf),
+        )
+      } else {
+        let path = flags.path;
+        match File::open(context.state.cwd().join(path)) {
+          Ok(mut file) => copy_all_but_last_lines(
+            &mut context.stdout,
+            skip_last,
+            context.state.kill_signal(),
+            |buf| file.read(buf).map_err(Into::into),
+          ),
+          Err(err) => {
+            context.stderr.write_line(&format!(
+              "head: {}: {}",
+              path.to_string_lossy(),
+              err
+            ))?;
+            Ok(ExecuteResult::from_exit_code(1))
+          }
+        }
       }
     }
   }
 }
 
+#[derive(Debug, PartialEq, Clone, Copy)]
+enum LineCount {
+  /// print first N lines
+  First(u64),
+  /// print all but last N lines
+  AllButLast(u64),
+}
+
 #[derive(Debug, PartialEq)]
 struct HeadFlags<'a> {
   path: &'a OsStr,
-  lines: u64,
+  lines: LineCount,
+}
+
+fn parse_line_count(s: &str) -> Result<LineCount> {
+  if let Some(rest) = s.strip_prefix('-') {
+    let num = rest.parse::<u64>()?;
+    Ok(LineCount::AllButLast(num))
+  } else {
+    let num = s.parse::<u64>()?;
+    Ok(LineCount::First(num))
+  }
 }
 
 fn parse_args<'a>(args: &'a [OsString]) -> Result<HeadFlags<'a>> {
   let mut path: Option<&'a OsStr> = None;
-  let mut lines: Option<u64> = None;
+  let mut lines: Option<LineCount> = None;
   let mut iterator = parse_arg_kinds(args).into_iter();
   while let Some(arg) = iterator.next() {
     match arg {
@@ -137,9 +237,11 @@ fn parse_args<'a>(args: &'a [OsString]) -> Result<HeadFlags<'a>> {
       }
       ArgKind::ShortFlag('n') => match iterator.next() {
         Some(ArgKind::Arg(arg)) => {
-          let num = arg.to_str().and_then(|a| a.parse::<u64>().ok());
-          if let Some(num) = num {
-            lines = Some(num);
+          if let Some(s) = arg.to_str() {
+            match parse_line_count(s) {
+              Ok(count) => lines = Some(count),
+              Err(_) => bail!("expected a numeric value following -n"),
+            }
           } else {
             bail!("expected a numeric value following -n")
           }
@@ -150,7 +252,7 @@ fn parse_args<'a>(args: &'a [OsString]) -> Result<HeadFlags<'a>> {
         if flag == "lines" || flag == "lines=" {
           bail!("expected a value for --lines");
         } else if let Some(arg) = flag.strip_prefix("lines=") {
-          lines = Some(arg.parse::<u64>()?);
+          lines = Some(parse_line_count(arg)?);
         } else {
           arg.bail_unsupported()?
         }
@@ -161,7 +263,7 @@ fn parse_args<'a>(args: &'a [OsString]) -> Result<HeadFlags<'a>> {
 
   Ok(HeadFlags {
     path: path.unwrap_or(OsStr::new("-")),
-    lines: lines.unwrap_or(10),
+    lines: lines.unwrap_or(LineCount::First(10)),
   })
 }
 
@@ -231,56 +333,78 @@ mod test {
       parse_args(&[]).unwrap(),
       HeadFlags {
         path: OsStr::new("-"),
-        lines: 10
+        lines: LineCount::First(10)
       }
     );
     assert_eq!(
       parse_args(&["-n".into(), "5".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("-"),
-        lines: 5
+        lines: LineCount::First(5)
       }
     );
     assert_eq!(
       parse_args(&["--lines=5".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("-"),
-        lines: 5
+        lines: LineCount::First(5)
       }
     );
     assert_eq!(
       parse_args(&["path".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("path"),
-        lines: 10
+        lines: LineCount::First(10)
       }
     );
     assert_eq!(
       parse_args(&["-n".into(), "5".into(), "path".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("path"),
-        lines: 5
+        lines: LineCount::First(5)
       }
     );
     assert_eq!(
       parse_args(&["--lines=5".into(), "path".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("path"),
-        lines: 5
+        lines: LineCount::First(5)
       }
     );
     assert_eq!(
       parse_args(&["path".into(), "-n".into(), "5".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("path"),
-        lines: 5
+        lines: LineCount::First(5)
       }
     );
     assert_eq!(
       parse_args(&["path".into(), "--lines=5".into()]).unwrap(),
       HeadFlags {
         path: OsStr::new("path"),
-        lines: 5
+        lines: LineCount::First(5)
+      }
+    );
+    // negative line counts (all but last N)
+    assert_eq!(
+      parse_args(&["-n".into(), "-1".into()]).unwrap(),
+      HeadFlags {
+        path: OsStr::new("-"),
+        lines: LineCount::AllButLast(1)
+      }
+    );
+    assert_eq!(
+      parse_args(&["-n".into(), "-5".into(), "path".into()]).unwrap(),
+      HeadFlags {
+        path: OsStr::new("path"),
+        lines: LineCount::AllButLast(5)
+      }
+    );
+    assert_eq!(
+      parse_args(&["--lines=-3".into()]).unwrap(),
+      HeadFlags {
+        path: OsStr::new("-"),
+        lines: LineCount::AllButLast(3)
       }
     );
     assert_eq!(
@@ -304,4 +428,83 @@ mod test {
       "unsupported flag: -t"
     );
   }
+
+  #[tokio::test]
+  async fn copies_all_but_last_lines() {
+    let (reader, mut writer) = pipe();
+    let reader_handle = reader.pipe_to_string_handle();
+    let data = b"line1\nline2\nline3\nline4\nline5\n";
+    let mut offset = 0;
+    let result = copy_all_but_last_lines(
+      &mut writer,
+      1,
+      &KillSignal::default(),
+      |buffer| {
+        if offset >= data.len() {
+          return Ok(0);
+        }
+        let read_length = min(buffer.len(), data.len() - offset);
+        buffer[..read_length]
+          .copy_from_slice(&data[offset..(offset + read_length)]);
+        offset += read_length;
+        Ok(read_length)
+      },
+    );
+    drop(writer);
+    assert_eq!(reader_handle.await.unwrap(), "line1\nline2\nline3\nline4\n");
+    assert_eq!(result.unwrap().into_exit_code_and_handles().0, 0);
+  }
+
+  #[tokio::test]
+  async fn copies_all_but_last_two_lines() {
+    let (reader, mut writer) = pipe();
+    let reader_handle = reader.pipe_to_string_handle();
+    let data = b"line1\nline2\nline3\nline4\nline5\n";
+    let mut offset = 0;
+    let result = copy_all_but_last_lines(
+      &mut writer,
+      2,
+      &KillSignal::default(),
+      |buffer| {
+        if offset >= data.len() {
+          return Ok(0);
+        }
+        let read_length = min(buffer.len(), data.len() - offset);
+        buffer[..read_length]
+          .copy_from_slice(&data[offset..(offset + read_length)]);
+        offset += read_length;
+        Ok(read_length)
+      },
+    );
+    drop(writer);
+    assert_eq!(reader_handle.await.unwrap(), "line1\nline2\nline3\n");
+    assert_eq!(result.unwrap().into_exit_code_and_handles().0, 0);
+  }
+
+  #[tokio::test]
+  async fn copies_all_but_last_lines_when_skip_exceeds_total() {
+    let (reader, mut writer) = pipe();
+    let reader_handle = reader.pipe_to_string_handle();
+    let data = b"line1\nline2\n";
+    let mut offset = 0;
+    let result = copy_all_but_last_lines(
+      &mut writer,
+      5,
+      &KillSignal::default(),
+      |buffer| {
+        if offset >= data.len() {
+          return Ok(0);
+        }
+        let read_length = min(buffer.len(), data.len() - offset);
+        buffer[..read_length]
+          .copy_from_slice(&data[offset..(offset + read_length)]);
+        offset += read_length;
+        Ok(read_length)
+      },
+    );
+    drop(writer);
+    // when skip_last >= total_lines, output should be empty
+    assert_eq!(reader_handle.await.unwrap(), "");
+    assert_eq!(result.unwrap().into_exit_code_and_handles().0, 0);
+  }
 }
diff --git a/tests/integration_test.rs b/tests/integration_test.rs
index 362c86c..ba94079 100644
--- a/tests/integration_test.rs
+++ b/tests/integration_test.rs
@@ -953,6 +953,46 @@ async fn head() {
     .assert_stdout("foo\nbar\nbaz\n")
     .run()
     .await;
+
+  // negative line count: -n -1 (all but last 1 line)
+  TestBuilder::new()
+    .command("head -n -1")
+    .stdin("line1\nline2\nline3\nline4\nline5\n")
+    .assert_stdout("line1\nline2\nline3\nline4\n")
+    .run()
+    .await;
+
+  // negative line count: -n -2 (all but last 2 lines)
+  TestBuilder::new()
+    .command("head -n -2")
+    .stdin("line1\nline2\nline3\nline4\nline5\n")
+    .assert_stdout("line1\nline2\nline3\n")
+    .run()
+    .await;
+
+  // negative line count with --lines
+  TestBuilder::new()
+    .command("head --lines=-3")
+    .stdin("line1\nline2\nline3\nline4\nline5\n")
+    .assert_stdout("line1\nline2\n")
+    .run()
+    .await;
+
+  // negative line count with file
+  TestBuilder::new()
+    .command("head -n -1 file")
+    .file("file", "line1\nline2\nline3\nline4\nline5\n")
+    .assert_stdout("line1\nline2\nline3\nline4\n")
+    .run()
+    .await;
+
+  // negative line count where skip >= total lines (empty output)
+  TestBuilder::new()
+    .command("head -n -10")
+    .stdin("line1\nline2\nline3\n")
+    .assert_stdout("")
+    .run()
+    .await;
 }
 
 // Basic integration tests as there are unit tests in the commands