diff --git a/tests/test_items.py b/tests/test_items.py
index cf6134aa..50713486 100644
--- a/tests/test_items.py
+++ b/tests/test_items.py
@@ -328,6 +328,42 @@ def test_key_automatically_sets_proper_string_type_if_not_bare() -> None:
     assert key.t == KeyType.Basic
 
 
+@pytest.mark.parametrize(
+    "k, t",
+    [
+        ("", KeyType.Bare),
+        ("foo bar", KeyType.Bare),
+        ("foo.bar", KeyType.Bare),
+        ("é", KeyType.Bare),
+        ('a = "x"\nb', KeyType.Bare),
+        ("a'b", KeyType.Literal),
+        ("a\nb", KeyType.Literal),
+        ("a\x7fb", KeyType.Literal),
+    ],
+)
+def test_key_rejects_text_invalid_for_explicit_type(k: str, t: KeyType) -> None:
+    with pytest.raises(ValueError):
+        Key(k, t)
+
+
+@pytest.mark.parametrize(
+    "k, t, expected",
+    [
+        ("foo-bar_1", KeyType.Bare, "foo-bar_1"),
+        ("", KeyType.Literal, "''"),
+        ('a.b "c"\td', KeyType.Literal, "'a.b \"c\"\td'"),
+        ("a'\nb", KeyType.Basic, '"a\'\\nb"'),
+    ],
+)
+def test_key_with_explicit_type_round_trips(k: str, t: KeyType, expected: str) -> None:
+    key = Key(k, t)
+    assert key.as_string() == expected
+
+    doc = api.document()
+    doc.add(key, 1)
+    assert parse(doc.as_string()) == {k: 1}
+
+
 @pytest.mark.parametrize(
     "index, replacement",
     [
diff --git a/tomlkit/items.py b/tomlkit/items.py
index 8589df97..18c8cc70 100644
--- a/tomlkit/items.py
+++ b/tomlkit/items.py
@@ -404,6 +404,13 @@ def __repr__(self) -> str:
         return f"<Key {self.as_string()}>"
 
 
+_BARE_KEY_CHARS = frozenset(string.ascii_letters + string.digits + "-_")
+
+
+def _is_bare_key(k: str) -> bool:
+    return bool(k) and all(c in _BARE_KEY_CHARS for c in k)
+
+
 class SingleKey(Key):
     """A single key"""
 
@@ -418,12 +425,17 @@ def __init__(
             raise TypeError("Keys must be strings")
 
         if t is None:
-            if not k or any(
-                c not in string.ascii_letters + string.digits + "-" + "_" for c in k
+            t = KeyType.Bare if _is_bare_key(k) else KeyType.Basic
+        elif original is None:
+            # Bare and literal keys are emitted verbatim, so reject keys
+            # that cannot be written that way instead of producing TOML
+            # that parses with a different structure.
+            if t == KeyType.Bare and not _is_bare_key(k):
+                raise ValueError(f"Invalid bare key: {k!r}")
+            if t == KeyType.Literal and any(
+                c in StringType.SLL.invalid_sequences for c in k
             ):
-                t = KeyType.Basic
-            else:
-                t = KeyType.Bare
+                raise ValueError(f"Invalid literal key: {k!r}")
 
         self.t = t
         if sep is None: