diff --git a/crates/agent/src/shell_parser.rs b/crates/agent/src/shell_parser.rs
index 25825ea341e753fc17847937b738e2c05d92ed93..e120799355b905ebf3cddc962132d0f7941faa1b 100644
--- a/crates/agent/src/shell_parser.rs
+++ b/crates/agent/src/shell_parser.rs
@@ -65,8 +65,26 @@ fn extract_commands_from_command(command: &ast::Command, commands: &mut Vec<Stri
         ast::Command::Simple(simple_command) => {
             extract_commands_from_simple_command(simple_command, commands)?;
         }
-        ast::Command::Compound(compound_command, _redirect_list) => {
-            extract_commands_from_compound_command(compound_command, commands)?;
+        ast::Command::Compound(compound_command, redirect_list) => {
+            let body_start = extract_commands_from_compound_command(compound_command, commands)?;
+            if let Some(redirect_list) = redirect_list {
+                let mut normalized_redirects = Vec::new();
+                for redirect in &redirect_list.0 {
+                    match normalize_io_redirect(redirect)? {
+                        RedirectNormalization::Normalized(s) => normalized_redirects.push(s),
+                        RedirectNormalization::Skip => {}
+                    }
+                }
+                if !normalized_redirects.is_empty() {
+                    if body_start >= commands.len() {
+                        return None;
+                    }
+                    commands.extend(normalized_redirects);
+                }
+                for redirect in &redirect_list.0 {
+                    extract_commands_from_io_redirect(redirect, commands)?;
+                }
+            }
         }
         ast::Command::Function(func_def) => {
             extract_commands_from_function_body(&func_def.body, commands)?;
@@ -78,6 +96,11 @@ fn extract_commands_from_command(command: &ast::Command, commands: &mut Vec<Stri
     Some(())
 }
 
+enum RedirectNormalization {
+    Normalized(String),
+    Skip,
+}
+
 fn extract_commands_from_simple_command(
     simple_command: &ast::SimpleCommand,
     commands: &mut Vec<String>,
@@ -90,27 +113,56 @@ fn extract_commands_from_simple_command(
     // returns None — the same as a shell parse failure. The caller then falls
     // back to raw-input matching with always_allow disabled.
     let mut words = Vec::new();
+    let mut redirects = Vec::new();
+
+    if let Some(prefix) = &simple_command.prefix {
+        for item in &prefix.0 {
+            if let ast::CommandPrefixOrSuffixItem::IoRedirect(redirect) = item {
+                match normalize_io_redirect(redirect) {
+                    Some(RedirectNormalization::Normalized(s)) => redirects.push(s),
+                    Some(RedirectNormalization::Skip) => {}
+                    None => return None,
+                }
+            }
+        }
+    }
     if let Some(word) = &simple_command.word_or_name {
         words.push(normalize_word(word)?);
     }
     if let Some(suffix) = &simple_command.suffix {
         for item in &suffix.0 {
-            if let ast::CommandPrefixOrSuffixItem::Word(word) = item {
-                words.push(normalize_word(word)?);
+            match item {
+                ast::CommandPrefixOrSuffixItem::Word(word) => {
+                    words.push(normalize_word(word)?);
+                }
+                ast::CommandPrefixOrSuffixItem::IoRedirect(redirect) => {
+                    match normalize_io_redirect(redirect) {
+                        Some(RedirectNormalization::Normalized(s)) => redirects.push(s),
+                        Some(RedirectNormalization::Skip) => {}
+                        None => return None,
+                    }
+                }
+                _ => {}
             }
         }
     }
+
+    if words.is_empty() && !redirects.is_empty() {
+        return None;
+    }
+
     let command_str = words.join(" ");
     if !command_str.is_empty() {
         commands.push(command_str);
     }
+    commands.extend(redirects);
 
     // Extract nested commands from command substitutions, process substitutions, etc.
     if let Some(prefix) = &simple_command.prefix {
         extract_commands_from_command_prefix(prefix, commands)?;
     }
     if let Some(word) = &simple_command.word_or_name {
-        extract_commands_from_word(word, commands);
+        extract_commands_from_word(word, commands)?;
     }
     if let Some(suffix) = &simple_command.suffix {
         extract_commands_from_command_suffix(suffix, commands)?;
@@ -131,7 +183,7 @@ fn normalize_word(word: &ast::Word) -> Option<String> {
             piece_with_source.start_index,
             piece_with_source.end_index,
             &mut result,
-        );
+        )?;
     }
     Some(result)
 }
@@ -142,7 +194,7 @@ fn normalize_word_piece_into(
     start_index: usize,
     end_index: usize,
     result: &mut String,
-) {
+) -> Option<()> {
     match piece {
         WordPiece::Text(text) => result.push_str(text),
         WordPiece::SingleQuotedText(text) => result.push_str(text),
@@ -159,7 +211,7 @@ fn normalize_word_piece_into(
                     inner.start_index,
                     inner.end_index,
                     result,
-                );
+                )?;
             }
         }
         WordPiece::TildePrefix(prefix) => {
@@ -173,9 +225,53 @@ fn normalize_word_piece_into(
         | WordPiece::CommandSubstitution(_)
         | WordPiece::BackquotedCommandSubstitution(_)
         | WordPiece::ArithmeticExpression(_) => {
-            if let Some(source) = raw_value.get(start_index..end_index) {
-                result.push_str(source);
-            }
+            let source = raw_value.get(start_index..end_index)?;
+            result.push_str(source);
+        }
+    }
+    Some(())
+}
+
+fn normalize_io_redirect(redirect: &ast::IoRedirect) -> Option<RedirectNormalization> {
+    match redirect {
+        ast::IoRedirect::File(fd, kind, target) => {
+            let target_word = match target {
+                ast::IoFileRedirectTarget::Filename(word) => word,
+                _ => return Some(RedirectNormalization::Skip),
+            };
+            let operator = match kind {
+                ast::IoFileRedirectKind::Read => "<",
+                ast::IoFileRedirectKind::Write => ">",
+                ast::IoFileRedirectKind::Append => ">>",
+                ast::IoFileRedirectKind::ReadAndWrite => "<>",
+                ast::IoFileRedirectKind::Clobber => ">|",
+                // The parser pairs DuplicateInput/DuplicateOutput with
+                // IoFileRedirectTarget::Duplicate (not Filename), so the
+                // target match above will return Skip before we reach here.
+                // These arms are kept for defensiveness.
+                ast::IoFileRedirectKind::DuplicateInput => "<&",
+                ast::IoFileRedirectKind::DuplicateOutput => ">&",
+            };
+            let fd_prefix = match fd {
+                Some(fd) => fd.to_string(),
+                None => String::new(),
+            };
+            let normalized = normalize_word(target_word)?;
+            Some(RedirectNormalization::Normalized(format!(
+                "{}{} {}",
+                fd_prefix, operator, normalized
+            )))
+        }
+        ast::IoRedirect::OutputAndError(word, append) => {
+            let operator = if *append { "&>>" } else { "&>" };
+            let normalized = normalize_word(word)?;
+            Some(RedirectNormalization::Normalized(format!(
+                "{} {}",
+                operator, normalized
+            )))
+        }
+        ast::IoRedirect::HereDocument(_, _) | ast::IoRedirect::HereString(_, _) => {
+            Some(RedirectNormalization::Skip)
         }
     }
 }
@@ -209,10 +305,10 @@ fn extract_commands_from_prefix_or_suffix_item(
             extract_commands_from_io_redirect(redirect, commands)?;
         }
         ast::CommandPrefixOrSuffixItem::AssignmentWord(assignment, _word) => {
-            extract_commands_from_assignment(assignment, commands);
+            extract_commands_from_assignment(assignment, commands)?;
         }
         ast::CommandPrefixOrSuffixItem::Word(word) => {
-            extract_commands_from_word(word, commands);
+            extract_commands_from_word(word, commands)?;
         }
         ast::CommandPrefixOrSuffixItem::ProcessSubstitution(_kind, subshell) => {
             extract_commands_from_compound_list(&subshell.list, commands)?;
@@ -226,59 +322,70 @@ fn extract_commands_from_io_redirect(
     commands: &mut Vec<String>,
 ) -> Option<()> {
     match redirect {
-        ast::IoRedirect::File(_fd, _kind, target) => {
-            if let ast::IoFileRedirectTarget::ProcessSubstitution(_kind, subshell) = target {
+        ast::IoRedirect::File(_fd, _kind, target) => match target {
+            ast::IoFileRedirectTarget::ProcessSubstitution(_kind, subshell) => {
                 extract_commands_from_compound_list(&subshell.list, commands)?;
             }
+            ast::IoFileRedirectTarget::Filename(word) => {
+                extract_commands_from_word(word, commands)?;
+            }
+            _ => {}
+        },
+        ast::IoRedirect::HereDocument(_fd, here_doc) => {
+            if here_doc.requires_expansion {
+                extract_commands_from_word(&here_doc.doc, commands)?;
+            }
         }
-        ast::IoRedirect::HereDocument(_fd, _here_doc) => {}
         ast::IoRedirect::HereString(_fd, word) => {
-            extract_commands_from_word(word, commands);
+            extract_commands_from_word(word, commands)?;
         }
         ast::IoRedirect::OutputAndError(word, _) => {
-            extract_commands_from_word(word, commands);
+            extract_commands_from_word(word, commands)?;
         }
     }
     Some(())
 }
 
-fn extract_commands_from_assignment(assignment: &ast::Assignment, commands: &mut Vec<String>) {
+fn extract_commands_from_assignment(
+    assignment: &ast::Assignment,
+    commands: &mut Vec<String>,
+) -> Option<()> {
     match &assignment.value {
         ast::AssignmentValue::Scalar(word) => {
-            extract_commands_from_word(word, commands);
+            extract_commands_from_word(word, commands)?;
         }
         ast::AssignmentValue::Array(words) => {
             for (opt_word, word) in words {
                 if let Some(w) = opt_word {
-                    extract_commands_from_word(w, commands);
+                    extract_commands_from_word(w, commands)?;
                 }
-                extract_commands_from_word(word, commands);
+                extract_commands_from_word(word, commands)?;
             }
         }
     }
+    Some(())
 }
 
-fn extract_commands_from_word(word: &ast::Word, commands: &mut Vec<String>) {
+fn extract_commands_from_word(word: &ast::Word, commands: &mut Vec<String>) -> Option<()> {
     let options = ParserOptions::default();
-    if let Ok(pieces) = brush_parser::word::parse(&word.value, &options) {
-        for piece_with_source in pieces {
-            extract_commands_from_word_piece(&piece_with_source.piece, commands);
-        }
+    let pieces = brush_parser::word::parse(&word.value, &options).ok()?;
+    for piece_with_source in pieces {
+        extract_commands_from_word_piece(&piece_with_source.piece, commands)?;
     }
+    Some(())
 }
 
-fn extract_commands_from_word_piece(piece: &WordPiece, commands: &mut Vec<String>) {
+fn extract_commands_from_word_piece(piece: &WordPiece, commands: &mut Vec<String>) -> Option<()> {
     match piece {
         WordPiece::CommandSubstitution(cmd_str)
         | WordPiece::BackquotedCommandSubstitution(cmd_str) => {
-            if let Some(nested_commands) = extract_commands(cmd_str) {
-                commands.extend(nested_commands);
-            }
+            let nested_commands = extract_commands(cmd_str)?;
+            commands.extend(nested_commands);
         }
         WordPiece::DoubleQuotedSequence(pieces)
         | WordPiece::GettextDoubleQuotedSequence(pieces) => {
             for inner_piece_with_source in pieces {
-                extract_commands_from_word_piece(&inner_piece_with_source.piece, commands);
+                extract_commands_from_word_piece(&inner_piece_with_source.piece, commands)?;
             }
         }
         WordPiece::EscapeSequence(_)
@@ -289,37 +396,47 @@ fn extract_commands_from_word_piece(piece: &WordPiece, commands: &mut Vec<String
         | WordPiece::ParameterExpansion(_)
         | WordPiece::ArithmeticExpression(_) => {}
     }
+    Some(())
 }
 
 fn extract_commands_from_compound_command(
     compound_command: &ast::CompoundCommand,
     commands: &mut Vec<String>,
-) -> Option<()> {
+) -> Option<usize> {
     match compound_command {
         ast::CompoundCommand::BraceGroup(brace_group) => {
+            let body_start = commands.len();
             extract_commands_from_compound_list(&brace_group.list, commands)?;
+            Some(body_start)
         }
         ast::CompoundCommand::Subshell(subshell) => {
+            let body_start = commands.len();
             extract_commands_from_compound_list(&subshell.list, commands)?;
+            Some(body_start)
         }
         ast::CompoundCommand::ForClause(for_clause) => {
             if let Some(words) = &for_clause.values {
                 for word in words {
-                    extract_commands_from_word(word, commands);
+                    extract_commands_from_word(word, commands)?;
                 }
             }
+            let body_start = commands.len();
             extract_commands_from_do_group(&for_clause.body, commands)?;
+            Some(body_start)
         }
         ast::CompoundCommand::CaseClause(case_clause) => {
-            extract_commands_from_word(&case_clause.value, commands);
+            extract_commands_from_word(&case_clause.value, commands)?;
+            let body_start = commands.len();
             for item in &case_clause.cases {
                 if let Some(body) = &item.cmd {
                     extract_commands_from_compound_list(body, commands)?;
                 }
             }
+            Some(body_start)
         }
         ast::CompoundCommand::IfClause(if_clause) => {
             extract_commands_from_compound_list(&if_clause.condition, commands)?;
+            let body_start = commands.len();
             extract_commands_from_compound_list(&if_clause.then, commands)?;
             if let Some(elses) = &if_clause.elses {
                 for else_item in elses {
@@ -329,18 +446,22 @@ fn extract_commands_from_compound_command(
                     extract_commands_from_compound_list(&else_item.body, commands)?;
                 }
             }
+            Some(body_start)
         }
         ast::CompoundCommand::WhileClause(while_clause)
         | ast::CompoundCommand::UntilClause(while_clause) => {
             extract_commands_from_compound_list(&while_clause.0, commands)?;
+            let body_start = commands.len();
             extract_commands_from_do_group(&while_clause.1, commands)?;
+            Some(body_start)
         }
         ast::CompoundCommand::ArithmeticForClause(arith_for) => {
+            let body_start = commands.len();
             extract_commands_from_do_group(&arith_for.body, commands)?;
+            Some(body_start)
         }
-        ast::CompoundCommand::Arithmetic(_arith_cmd) => {}
+        ast::CompoundCommand::Arithmetic(_arith_cmd) => Some(commands.len()),
     }
-    Some(())
 }
 
 fn extract_commands_from_do_group(
@@ -354,7 +475,26 @@ fn extract_commands_from_function_body(
     func_body: &ast::FunctionBody,
     commands: &mut Vec<String>,
 ) -> Option<()> {
-    extract_commands_from_compound_command(&func_body.0, commands)
+    let body_start = extract_commands_from_compound_command(&func_body.0, commands)?;
+    if let Some(redirect_list) = &func_body.1 {
+        let mut normalized_redirects = Vec::new();
+        for redirect in &redirect_list.0 {
+            match normalize_io_redirect(redirect)? {
+                RedirectNormalization::Normalized(s) => normalized_redirects.push(s),
+                RedirectNormalization::Skip => {}
+            }
+        }
+        if !normalized_redirects.is_empty() {
+            if body_start >= commands.len() {
+                return None;
+            }
+            commands.extend(normalized_redirects);
+        }
+        for redirect in &redirect_list.0 {
+            extract_commands_from_io_redirect(redirect, commands)?;
+        }
+    }
+    Some(())
 }
 
 fn extract_commands_from_extended_test_expr(
@@ -380,11 +520,11 @@ fn extract_commands_from_extended_test_expr_inner(
             extract_commands_from_extended_test_expr_inner(inner, commands)?;
         }
         ast::ExtendedTestExpr::UnaryTest(_, word) => {
-            extract_commands_from_word(word, commands);
+            extract_commands_from_word(word, commands)?;
         }
         ast::ExtendedTestExpr::BinaryTest(_, word1, word2) => {
-            extract_commands_from_word(word1, commands);
-            extract_commands_from_word(word2, commands);
+            extract_commands_from_word(word1, commands)?;
+            extract_commands_from_word(word2, commands)?;
         }
     }
     Some(())
@@ -579,4 +719,275 @@ mod tests {
         let result = extract_commands("ls &&");
         assert!(result.is_none());
     }
+
+    #[test]
+    fn test_unparsable_nested_substitution_returns_none() {
+        let result = extract_commands("echo $(ls &&)");
+        assert!(result.is_none());
+    }
+
+    #[test]
+    fn test_unparsable_nested_backtick_substitution_returns_none() {
+        let result = extract_commands("echo `ls &&`");
+        assert!(result.is_none());
+    }
+
+    #[test]
+    fn test_redirect_write_includes_target_path() {
+        let commands = extract_commands("echo hello > /etc/passwd").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "> /etc/passwd"]);
+    }
+
+    #[test]
+    fn test_redirect_append_includes_target_path() {
+        let commands = extract_commands("cat file >> /tmp/log").expect("parse failed");
+        assert_eq!(commands, vec!["cat file", ">> /tmp/log"]);
+    }
+
+    #[test]
+    fn test_fd_redirect_handled_gracefully() {
+        let commands = extract_commands("cmd 2>&1").expect("parse failed");
+        assert_eq!(commands, vec!["cmd"]);
+    }
+
+    #[test]
+    fn test_input_redirect() {
+        let commands = extract_commands("sort < /tmp/input").expect("parse failed");
+        assert_eq!(commands, vec!["sort", "< /tmp/input"]);
+    }
+
+    #[test]
+    fn test_multiple_redirects() {
+        let commands = extract_commands("cmd > /tmp/out 2> /tmp/err").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", "> /tmp/out", "2> /tmp/err"]);
+    }
+
+    #[test]
+    fn test_prefix_position_redirect() {
+        let commands = extract_commands("> /tmp/out echo hello").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_redirect_with_variable_expansion() {
+        let commands = extract_commands("echo > $HOME/file").expect("parse failed");
+        assert_eq!(commands, vec!["echo", "> $HOME/file"]);
+    }
+
+    #[test]
+    fn test_output_and_error_redirect() {
+        let commands = extract_commands("cmd &> /tmp/all").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", "&> /tmp/all"]);
+    }
+
+    #[test]
+    fn test_append_output_and_error_redirect() {
+        let commands = extract_commands("cmd &>> /tmp/all").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", "&>> /tmp/all"]);
+    }
+
+    #[test]
+    fn test_redirect_in_chained_command() {
+        let commands =
+            extract_commands("echo hello > /tmp/out && cat /tmp/out").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "> /tmp/out", "cat /tmp/out"]);
+    }
+
+    #[test]
+    fn test_here_string_dropped_from_normalized_output() {
+        let commands = extract_commands("cat <<< 'hello'").expect("parse failed");
+        assert_eq!(commands, vec!["cat"]);
+    }
+
+    #[test]
+    fn test_brace_group_redirect() {
+        let commands = extract_commands("{ echo hello; } > /etc/passwd").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "> /etc/passwd"]);
+    }
+
+    #[test]
+    fn test_subshell_redirect() {
+        let commands = extract_commands("(cmd) > /etc/passwd").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", "> /etc/passwd"]);
+    }
+
+    #[test]
+    fn test_for_loop_redirect() {
+        let commands =
+            extract_commands("for f in *; do cat \"$f\"; done > /tmp/out").expect("parse failed");
+        assert_eq!(commands, vec!["cat $f", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_brace_group_multi_command_redirect() {
+        let commands =
+            extract_commands("{ echo hello; cat; } > /etc/passwd").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "cat", "> /etc/passwd"]);
+    }
+
+    #[test]
+    fn test_quoted_redirect_target_is_normalized() {
+        let commands = extract_commands("echo hello > '/etc/passwd'").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "> /etc/passwd"]);
+    }
+
+    #[test]
+    fn test_redirect_without_space() {
+        let commands = extract_commands("echo hello >/etc/passwd").expect("parse failed");
+        assert_eq!(commands, vec!["echo hello", "> /etc/passwd"]);
+    }
+
+    #[test]
+    fn test_clobber_redirect() {
+        let commands = extract_commands("cmd >| /tmp/file").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", ">| /tmp/file"]);
+    }
+
+    #[test]
+    fn test_fd_to_fd_redirect_skipped() {
+        let commands = extract_commands("cmd 1>&2").expect("parse failed");
+        assert_eq!(commands, vec!["cmd"]);
+    }
+
+    #[test]
+    fn test_bare_redirect_returns_none() {
+        let result = extract_commands("> /etc/passwd");
+        assert!(result.is_none());
+    }
+
+    #[test]
+    fn test_arithmetic_with_redirect_returns_none() {
+        let result = extract_commands("(( x = 1 )) > /tmp/file");
+        assert!(result.is_none());
+    }
+
+    #[test]
+    fn test_redirect_target_with_command_substitution() {
+        let commands = extract_commands("echo > $(mktemp)").expect("parse failed");
+        assert_eq!(commands, vec!["echo", "> $(mktemp)", "mktemp"]);
+    }
+
+    #[test]
+    fn test_nested_compound_redirects() {
+        let commands = extract_commands("{ echo > /tmp/a; } > /tmp/b").expect("parse failed");
+        assert_eq!(commands, vec!["echo", "> /tmp/a", "> /tmp/b"]);
+    }
+
+    #[test]
+    fn test_while_loop_redirect() {
+        let commands =
+            extract_commands("while true; do echo line; done > /tmp/log").expect("parse failed");
+        assert_eq!(commands, vec!["true", "echo line", "> /tmp/log"]);
+    }
+
+    #[test]
+    fn test_if_clause_redirect() {
+        let commands =
+            extract_commands("if true; then echo yes; fi > /tmp/out").expect("parse failed");
+        assert_eq!(commands, vec!["true", "echo yes", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_pipe_with_redirect_on_last_command() {
+        let commands = extract_commands("ls | grep foo > /tmp/out").expect("parse failed");
+        assert_eq!(commands, vec!["ls", "grep foo", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_pipe_with_stderr_redirect_on_first_command() {
+        let commands = extract_commands("ls 2>/dev/null | grep foo").expect("parse failed");
+        assert_eq!(commands, vec!["ls", "2> /dev/null", "grep foo"]);
+    }
+
+    #[test]
+    fn test_function_definition_redirect() {
+        let commands = extract_commands("f() { echo hi; } > /tmp/out").expect("parse failed");
+        assert_eq!(commands, vec!["echo hi", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_read_and_write_redirect() {
+        let commands = extract_commands("cmd <> /dev/tty").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", "<> /dev/tty"]);
+    }
+
+    #[test]
+    fn test_case_clause_with_redirect() {
+        let commands =
+            extract_commands("case $x in a) echo hi;; esac > /tmp/out").expect("parse failed");
+        assert_eq!(commands, vec!["echo hi", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_until_loop_with_redirect() {
+        let commands =
+            extract_commands("until false; do echo line; done > /tmp/log").expect("parse failed");
+        assert_eq!(commands, vec!["false", "echo line", "> /tmp/log"]);
+    }
+
+    #[test]
+    fn test_arithmetic_for_clause_with_redirect() {
+        let commands = extract_commands("for ((i=0; i<10; i++)); do echo $i; done > /tmp/out")
+            .expect("parse failed");
+        assert_eq!(commands, vec!["echo $i", "> /tmp/out"]);
+    }
+
+    #[test]
+    fn test_if_elif_else_with_redirect() {
+        let commands = extract_commands(
+            "if true; then echo a; elif false; then echo b; else echo c; fi > /tmp/out",
+        )
+        .expect("parse failed");
+        assert_eq!(
+            commands,
+            vec!["true", "echo a", "false", "echo b", "echo c", "> /tmp/out"]
+        );
+    }
+
+    #[test]
+    fn test_multiple_redirects_on_compound_command() {
+        let commands = extract_commands("{ cmd; } > /tmp/out 2> /tmp/err").expect("parse failed");
+        assert_eq!(commands, vec!["cmd", "> /tmp/out", "2> /tmp/err"]);
+    }
+
+    #[test]
+    fn test_here_document_command_substitution_extracted() {
+        let commands = extract_commands("cat <<EOF\n$(rm -rf /)\nEOF").expect("parse failed");
+        assert!(commands.iter().any(|c| c.contains("cat")));
+        assert!(commands.contains(&"rm -rf /".to_string()));
+    }
+
+    #[test]
+    fn test_here_document_quoted_delimiter_no_extraction() {
+        let commands = extract_commands("cat <<'EOF'\n$(rm -rf /)\nEOF").expect("parse failed");
+        assert_eq!(commands, vec!["cat"]);
+    }
+
+    #[test]
+    fn test_here_document_backtick_substitution_extracted() {
+        let commands = extract_commands("cat <<EOF\n`whoami`\nEOF").expect("parse failed");
+        assert!(commands.iter().any(|c| c.contains("cat")));
+        assert!(commands.contains(&"whoami".to_string()));
+    }
+
+    #[test]
+    fn test_brace_group_redirect_with_command_substitution() {
+        let commands = extract_commands("{ echo hello; } > $(mktemp)").expect("parse failed");
+        assert!(commands.contains(&"echo hello".to_string()));
+        assert!(commands.contains(&"mktemp".to_string()));
+    }
+
+    #[test]
+    fn test_function_definition_redirect_with_command_substitution() {
+        let commands = extract_commands("f() { echo hi; } > $(mktemp)").expect("parse failed");
+        assert!(commands.contains(&"echo hi".to_string()));
+        assert!(commands.contains(&"mktemp".to_string()));
+    }
+
+    #[test]
+    fn test_brace_group_redirect_with_process_substitution() {
+        let commands = extract_commands("{ cat; } > >(tee /tmp/log)").expect("parse failed");
+        assert!(commands.contains(&"cat".to_string()));
+        assert!(commands.contains(&"tee /tmp/log".to_string()));
+    }
 }