diff --git a/README.md b/README.md
index 8e24014..da51fc9 100644
--- a/README.md
+++ b/README.md
@@ -114,6 +114,10 @@ Shell syntax such as pipes, redirections, environment-variable expansion, `*`, a
 This avoids shell startup overhead and the noise from correcting for it, especially for fast commands
 (< 5 ms).
 
+Commands containing unquoted, standalone shell operators such as `&&` or `>` require an explicit
+choice: use `-S` / `--shell=default` to interpret shell syntax, or `-N` / `--shell=none` to pass
+the operators as literal arguments.
+
 To enable shell syntax, use `-S` (an alias for `--shell=default`). This selects `sh`
 on Unix (resolved through `PATH`) or `cmd.exe` on Windows:
 ```sh
diff --git a/src/main.rs b/src/main.rs
index 9fe6e5c..0b3bdd9 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -11,9 +11,9 @@ use cli::get_cli_arguments;
 use command::Commands;
 use error::ConsoleOutputError;
 use export::ExportManager;
-use options::Options;
+use options::{ExecutorKind, Options};
 
-use anyhow::Result;
+use anyhow::{bail, Result};
 use colored::*;
 
 pub mod benchmark;
@@ -27,6 +27,7 @@ pub mod outlier_detection;
 pub mod output;
 pub mod parameter;
 pub mod quantity;
+pub mod shell_syntax;
 pub mod timer;
 pub mod util;
 
@@ -40,6 +41,27 @@ fn run() -> Result<()> {
     let commands = Commands::from_cli_arguments(&cli_arguments)?;
     options.validate_against_command_list(&commands)?;
 
+    if matches!(options.executor_kind, ExecutorKind::Raw)
+        && !cli_arguments.get_flag("no-shell")
+        && cli_arguments.get_one::<String>("shell").is_none()
+    {
+        for command in commands.iter() {
+            let command_line = command.get_command_line();
+            if let Some(operator) = shell_syntax::first_unquoted_operator(&command_line) {
+                bail!(
+                    concat!(
+                        "Command '{command_line}' contains unquoted shell syntax ('{operator}').\n",
+                        "Explicitly choose how to execute it:\n",
+                        "  -S / --shell=default  Interpret shell syntax.\n",
+                        "  -N / --shell=none     Run directly, passing '{operator}' as a literal argument.",
+                    ),
+                    command_line = command_line,
+                    operator = operator,
+                );
+            }
+        }
+    }
+
     let export_manager = ExportManager::from_cli_arguments(&cli_arguments, options.metrics[0])?;
 
     let mut scheduler = Scheduler::new(&commands, &options, &export_manager);
diff --git a/src/shell_syntax.rs b/src/shell_syntax.rs
new file mode 100644
index 0000000..caba560
--- /dev/null
+++ b/src/shell_syntax.rs
@@ -0,0 +1,218 @@
+//! Conservative detection of shell operators in commands run without a shell.
+
+use std::iter::Peekable;
+use std::str::CharIndices;
+
+/// Find the first standalone operator that is neither quoted nor escaped.
+///
+/// Operators attached to another word (such as `hello>out`), expansions, and
+/// other shell syntax are deliberately outside the scope of this check.
+pub fn first_unquoted_operator(command: &str) -> Option<&'static str> {
+    tokenize(command).find_map(|token| {
+        ["&&", "||", "|", ";", ">", ">>", "<"]
+            .iter()
+            .copied()
+            .find(|operator| {
+                // An escaped newline joins lines without quoting either side.
+                // All other quotes and escapes remain in the token, preventing
+                // it from matching an operator.
+                token
+                    .split("\\\n")
+                    .flat_map(str::bytes)
+                    .eq(operator.bytes())
+            })
+    })
+}
+
+/// Split words while preserving their original quoting and escaping.
+///
+/// Word boundaries and comments follow the same rules as `shell_words`, which
+/// parses commands for direct execution. This tokenizer neither expands shell
+/// expressions nor validates balanced quotes; command parsing handles errors.
+fn tokenize(command: &str) -> impl Iterator<Item = &str> {
+    Tokens {
+        command,
+        chars: command.char_indices().peekable(),
+    }
+}
+
+struct Tokens<'a> {
+    command: &'a str,
+    chars: Peekable<CharIndices<'a>>,
+}
+
+impl<'a> Iterator for Tokens<'a> {
+    type Item = &'a str;
+
+    fn next(&mut self) -> Option<Self::Item> {
+        // Whitespace, comments, and line continuations cannot start a word.
+        let start = loop {
+            let &(index, character) = self.chars.peek()?;
+            match character {
+                ' ' | '\t' | '\n' => {
+                    self.chars.next();
+                }
+                '#' => {
+                    for (_, character) in self.chars.by_ref() {
+                        if character == '\n' {
+                            break;
+                        }
+                    }
+                }
+                '\\' if self.chars.clone().nth(1).map(|(_, c)| c) == Some('\n') => {
+                    self.chars.next();
+                    self.chars.next();
+                }
+                _ => break index,
+            }
+        };
+
+        let mut quote = None;
+        while let Some((index, character)) = self.chars.next() {
+            match (quote, character) {
+                (Some('\''), '\'') | (Some('"'), '"') => quote = None,
+                (Some('\''), _) => {}
+                (_, '\\') => {
+                    // Within double quotes, skipping a non-special escaped
+                    // character is also safe: it cannot end the quoted word.
+                    self.chars.next();
+                }
+                (Some('"'), _) => {}
+                (None, '\'' | '"') => quote = Some(character),
+                (None, ' ' | '\t' | '\n') => return Some(&self.command[start..index]),
+                _ => {}
+            }
+        }
+
+        Some(&self.command[start..])
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::{first_unquoted_operator, tokenize};
+
+    #[test]
+    fn tokenizer_preserves_words_quotes_and_escapes() {
+        for (command, expected) in [
+            ("", vec![]),
+            (" \t\n", vec![]),
+            ("  echo\thello\nworld ", vec!["echo", "hello", "world"]),
+            (
+                r#"echo '' "" 'hello world'"#,
+                vec!["echo", "''", "\"\"", "'hello world'"],
+            ),
+            (
+                r#"echo pre'quoted part'"more"post"#,
+                vec!["echo", r#"pre'quoted part'"more"post"#],
+            ),
+            (
+                r"echo hello\ world \&\&",
+                vec!["echo", r"hello\ world", r"\&\&"],
+            ),
+            (r#"echo "a\" b" 'a\'"#, vec!["echo", r#""a\" b""#, r"'a\'"]),
+            ("echo hello>out", vec!["echo", "hello>out"]),
+            (
+                "echo café\t&&\n日本語",
+                vec!["echo", "café", "&&", "日本語"],
+            ),
+            ("echo a\r\u{a0}b", vec!["echo", "a\r\u{a0}b"]),
+        ] {
+            assert_eq!(
+                tokenize(command).collect::<Vec<_>>(),
+                expected,
+                "{command:?}"
+            );
+        }
+    }
+
+    #[test]
+    fn tokenizer_handles_comments_and_continuations() {
+        for (command, expected) in [
+            ("# ignored &&", vec![]),
+            (
+                "echo # ignored &&\nnext | cat",
+                vec!["echo", "next", "|", "cat"],
+            ),
+            (
+                r##"echo a#b \#c "#d" '#e'"##,
+                vec!["echo", "a#b", r"\#c", "\"#d\"", "'#e'"],
+            ),
+            ("\\\n echo \\\n&& more", vec!["echo", "&&", "more"]),
+            ("echo hello\\\nworld", vec!["echo", "hello\\\nworld"]),
+            ("\\\n# comment\necho", vec!["echo"]),
+        ] {
+            assert_eq!(
+                tokenize(command).collect::<Vec<_>>(),
+                expected,
+                "{command:?}"
+            );
+        }
+    }
+
+    #[test]
+    fn finds_supported_operators_in_command_order() {
+        for operator in ["&&", "||", "|", ";", ">", ">>", "<"] {
+            let command = format!("echo café\t{operator}\n日本語");
+            assert_eq!(first_unquoted_operator(&command), Some(operator));
+            assert_eq!(first_unquoted_operator(operator), Some(operator));
+        }
+        assert_eq!(first_unquoted_operator("echo a >> out && next"), Some(">>"));
+        assert_eq!(first_unquoted_operator("echo \\\n&& next"), Some("&&"));
+        assert_eq!(first_unquoted_operator("echo &\\\n& next"), Some("&&"));
+        assert_eq!(first_unquoted_operator("echo &&\\\n next"), Some("&&"));
+        assert_eq!(first_unquoted_operator("echo # &&\nnext | cat"), Some("|"));
+        assert_eq!(first_unquoted_operator(r#"echo "&&" || next"#), Some("||"));
+        assert_eq!(first_unquoted_operator(r"echo \&\& | cat"), Some("|"));
+    }
+
+    #[test]
+    fn ignores_quoted_escaped_and_attached_operators() {
+        for command in [
+            r#"echo "&&""#,
+            "echo '&&'",
+            r"echo \&\&",
+            r"echo &\&",
+            r#"echo '&'"&""#,
+            r#"echo ""&&"#,
+            "echo &&''",
+            r#"python -c "print(1 > 0)""#,
+            "sh -c 'true && false'",
+            r#"sh -c "echo 'a | b' && false""#,
+            r#"sh -c 'echo "a | b" && false'"#,
+            r#"echo "escaped \" && still quoted""#,
+            "echo hello>out",
+            "true&&false",
+            "echo a;",
+            "echo 2> out",
+            "echo >>> out",
+            "echo $VARIABLE *.rs ~/path NAME=value",
+            "echo # && ignored",
+            "echo foo#bar",
+            "echo\u{a0}&&",
+            "echo &&\r",
+        ] {
+            assert_eq!(first_unquoted_operator(command), None, "{command:?}");
+        }
+    }
+
+    #[test]
+    fn handles_empty_and_malformed_commands_without_panicking() {
+        for (command, expected) in [
+            ("", vec![]),
+            ("\\\n", vec![]),
+            ("\\", vec!["\\"]),
+            (r"echo \", vec!["echo", r"\"]),
+            ("echo 'unclosed &&", vec!["echo", "'unclosed &&"]),
+            ("echo \"unclosed &&", vec!["echo", "\"unclosed &&"]),
+            ("echo \"unclosed\\", vec!["echo", "\"unclosed\\"]),
+        ] {
+            assert_eq!(
+                tokenize(command).collect::<Vec<_>>(),
+                expected,
+                "{command:?}"
+            );
+            assert_eq!(first_unquoted_operator(command), None, "{command:?}");
+        }
+    }
+}
diff --git a/tests/integration_tests.rs b/tests/integration_tests.rs
index 529f84b..b4574e9 100644
--- a/tests/integration_tests.rs
+++ b/tests/integration_tests.rs
@@ -266,6 +266,42 @@ fn fails_with_duplicate_parameter_names() {
         .stderr(predicate::str::contains("Duplicate parameter names: x"));
 }
 
+#[test]
+fn requires_explicit_shell_for_shell_syntax() {
+    let directory = tempfile::tempdir().unwrap();
+
+    let assert = hyperfine()
+        .current_dir(directory.path())
+        .arg("rm -rf cache/ && ./my_command")
+        .assert()
+        .failure();
+
+    insta::assert_snapshot!(String::from_utf8_lossy(&assert.get_output().stderr), @"
+    Error: Command 'rm -rf cache/ && ./my_command' contains unquoted shell syntax ('&&').
+    Explicitly choose how to execute it:
+      -S / --shell=default  Interpret shell syntax.
+      -N / --shell=none     Run directly, passing '&&' as a literal argument.
+    ");
+
+    hyperfine()
+        .arg("--show-output")
+        .arg("--command-name=benchmark")
+        .args(["--shell=default", "--runs=1", "echo before && echo after"])
+        .assert()
+        .success()
+        .stdout(predicate::str::contains("before"))
+        .stdout(predicate::str::contains("after"))
+        .stdout(predicate::str::contains("&&").not());
+
+    hyperfine()
+        .arg("--show-output")
+        .arg("--command-name=benchmark")
+        .args(["--shell=none", "--runs=1", "echo before && echo after"])
+        .assert()
+        .success()
+        .stdout(predicate::str::contains("before && echo after"));
+}
+
 #[test]
 fn fails_for_unknown_command() {
     hyperfine()