diff --git a/mycli/packages/hybrid_redirection.py b/mycli/packages/hybrid_redirection.py
index 1937daf9..9312eea9 100644
--- a/mycli/packages/hybrid_redirection.py
+++ b/mycli/packages/hybrid_redirection.py
@@ -125,6 +125,7 @@ def invalid_shell_part(
     return False
 
 
+# todo there are still corner cases combining custom delimiters, caching, and redirection
 @functools.lru_cache(maxsize=1)
 def get_redirect_components(command: str) -> tuple[str | None, str | None, str | None, str | None]:
     """Get the parts of a hybrid shell-style redirect command."""
diff --git a/test/pytests/test_hybrid_redirection.py b/test/pytests/test_hybrid_redirection.py
new file mode 100644
index 00000000..1b6d79b0
--- /dev/null
+++ b/test/pytests/test_hybrid_redirection.py
@@ -0,0 +1,135 @@
+from typing import Generator
+
+import pytest
+import sqlglot
+
+from mycli.packages import hybrid_redirection
+
+
+def tokenize(command: str) -> list[sqlglot.Token]:
+    return sqlglot.tokenize(command)
+
+
+@pytest.fixture()
+def reset_hybrid_redirection(monkeypatch) -> Generator[None, None, None]:
+    monkeypatch.setattr(hybrid_redirection, 'WIN', False)
+    original_delimiter = hybrid_redirection.delimiter_command.current
+    hybrid_redirection.delimiter_command._delimiter = ';'
+    yield
+    hybrid_redirection.delimiter_command._delimiter = original_delimiter
+
+
+def test_find_token_indices_tracks_true_dollars_and_operators() -> None:
+    tokens = tokenize('select 1 $| cat $>> out.txt')
+
+    assert hybrid_redirection.find_token_indices(tokens) == {
+        'raw_dollar': [2, 5],
+        'true_dollar': [2, 5],
+        'angle_bracket': [6],
+        'pipe': [3],
+    }
+
+
+# todo there are still corner cases combining custom delimiters and redirection
+def test_find_sql_part_handles_valid_parse_custom_delimiter_and_invalid_sql(reset_hybrid_redirection) -> None:
+    hybrid_redirection.delimiter_command._delimiter = '$$'
+    valid_tokens = tokenize('select 1 $$ $> out.txt')
+    assert hybrid_redirection.find_sql_part('select 1 $$ $> out.txt', valid_tokens, [3]) == 'select 1'
+
+    invalid_tokens = tokenize('select from $> out.txt')
+    assert hybrid_redirection.find_sql_part('select from $> out.txt', invalid_tokens, [2]) == ''
+
+    multiple_tokens = tokenize('select 1; select 2 $> out.txt')
+    assert hybrid_redirection.find_sql_part('select 1; select 2 $> out.txt', multiple_tokens, [5]) == ''
+
+
+def test_find_command_and_file_tokens_extract_expected_parts() -> None:
+    tokens = tokenize('select 1 $| cat $>> out.txt')
+    indices = hybrid_redirection.find_token_indices(tokens)
+
+    file_tokens, file_index, operator = hybrid_redirection.find_file_tokens(tokens, indices['angle_bracket'])
+    command_tokens = hybrid_redirection.find_command_tokens(tokens[0:file_index], indices['true_dollar'])
+
+    assert operator == '>>'
+    assert file_index == 6
+    assert hybrid_redirection.assemble_tokens(file_tokens) == 'out.txt'
+    assert hybrid_redirection.assemble_tokens(command_tokens) == 'cat'
+
+
+def test_find_file_tokens_returns_empty_when_no_redirect_file() -> None:
+    tokens = tokenize('select 1 $| cat')
+
+    file_tokens, file_index, operator = hybrid_redirection.find_file_tokens(tokens, [])
+
+    assert file_tokens == []
+    assert file_index == len(tokens)
+    assert operator is None
+
+
+def test_assemble_tokens_quotes_identifier_and_string() -> None:
+    identifier_tokens = tokenize('echo hi $> "quoted.txt"')[4:]
+    string_tokens = tokenize("echo hi $| 'printf'")[4:]
+
+    assert hybrid_redirection.assemble_tokens(identifier_tokens) == '"quoted.txt"'
+    assert hybrid_redirection.assemble_tokens(string_tokens) == "'printf'"
+
+
+@pytest.mark.parametrize(
+    ('file_part', 'command_part', 'expected'),
+    [
+        ('two words.txt', None, True),
+        ('bad>file.txt', None, True),
+        (None, None, True),
+        ('out.txt', None, False),
+        (None, 'cat', False),
+    ],
+)
+def test_invalid_shell_part(file_part: str | None, command_part: str | None, expected: bool) -> None:
+    assert hybrid_redirection.invalid_shell_part(file_part, command_part) is expected
+
+
+def test_get_redirect_components_valid_paths_and_logging() -> None:
+    assert hybrid_redirection.get_redirect_components('select 1 $>> out.txt') == (
+        'select 1',
+        None,
+        '>>',
+        'out.txt',
+    )
+    assert hybrid_redirection.get_redirect_components('select 1 $| cat $> out.txt') == (
+        'select 1',
+        'cat',
+        '>',
+        'out.txt',
+    )
+
+
+def test_get_redirect_components_returns_none_on_token_error(monkeypatch) -> None:
+    monkeypatch.setattr(
+        hybrid_redirection.sqlglot, 'tokenize', lambda command: (_ for _ in ()).throw(sqlglot.errors.TokenError('bad token'))
+    )
+
+    assert hybrid_redirection.get_redirect_components('select 1 $> out.txt') == (None, None, None, None)
+
+
+def test_get_redirect_components_rejects_invalid_forms() -> None:
+    assert hybrid_redirection.get_redirect_components('select 1') == (None, None, None, None)
+    assert hybrid_redirection.get_redirect_components('select 1 $> out.txt $> other.txt') == (None, None, None, None)
+    assert hybrid_redirection.get_redirect_components('select 1 $> out.txt $| cat') == (None, None, None, None)
+    assert hybrid_redirection.get_redirect_components('select from $> out.txt') == (None, None, None, None)
+    assert hybrid_redirection.get_redirect_components('select 1 $> "two words.txt"') == (None, None, None, None)
+
+
+def test_get_redirect_components_rejects_multiple_pipes_on_windows(monkeypatch) -> None:
+    monkeypatch.setattr(hybrid_redirection, 'WIN', True)
+
+    assert hybrid_redirection.get_redirect_components('select 1 $| cat $| more') == (
+        None,
+        None,
+        None,
+        None,
+    )
+
+
+def test_is_redirect_command_reflects_component_parsing() -> None:
+    assert hybrid_redirection.is_redirect_command('select 1 $| cat') is True
+    assert hybrid_redirection.is_redirect_command('select 1') is False