diff --git a/CHANGELOG.md b/CHANGELOG.md
index 26584a1..92803ca 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,7 @@
 - Fix `comment()` producing invalid TOML for a multiline string by prefixing every line with `#`, not just the first. ([#449](https://github.com/python-poetry/tomlkit/issues/449))
 - Fix the separator comma being swallowed by a trailing comment when appending a key to a multiline inline table, leaving the new key without a separator so the result no longer round-trips. ([#512](https://github.com/python-poetry/tomlkit/issues/512))
 - Fix a `KeyAlreadyPresent` error when parsing or accessing an out-of-order table whose array-of-tables elements are split across the table's parts. ([#505](https://github.com/python-poetry/tomlkit/issues/505))
+- Fix a `KeyAlreadyPresent` error when a dotted-key header extension (e.g. `[fruit.apple.texture]`) appears after an unrelated table following an array-of-tables (e.g. `[[fruit]]`). ([#261](https://github.com/python-poetry/tomlkit/issues/261))
 
 ## [0.15.0] - 2026-05-10
 
diff --git a/README.md b/README.md
index 0baf4f8..e2decfc 100644
--- a/README.md
+++ b/README.md
@@ -26,6 +26,15 @@ Part of the implementation has been adapted, improved and fixed from [Molten](ht
 
 See the [documentation](https://tomlkit.readthedocs.io/) for more information.
 
+## Limitations
+
+`tomlkit` preserves the layout of parsed documents where it can. One known
+exception is an out-of-order sub-table that extends the last element of an array
+of tables, such as `[fruit.apple.texture]` appearing after an unrelated table
+following `[[fruit]]`. When the document is serialized again, that sub-table is
+emitted inside the array element it belongs to. Its data is preserved, but its
+physical position in the file is normalized.
+
 ## Installation
 
 If you are using [uv](https://docs.astral.sh/uv), you can
diff --git a/tests/test_toml_document.py b/tests/test_toml_document.py
index 1cdfb9c..a4edef5 100644
--- a/tests/test_toml_document.py
+++ b/tests/test_toml_document.py
@@ -667,6 +667,69 @@ def test_out_of_order_table_merges_three_aot_fragments() -> None:
     assert hooks["state"]["z"] == 3
 
 
+def test_aot_extension_via_dotted_key_after_unrelated_table() -> None:
+    content = """\
+[[fruit]]
+apple.color = "red"
+
+[potato]
+
+[fruit.apple.texture]
+smooth = true
+"""
+    doc = parse(content)
+    fruit = doc["fruit"]
+    assert len(fruit) == 1
+    assert fruit[0]["apple"]["color"] == "red"
+    assert fruit[0]["apple"]["texture"]["smooth"] is True
+    assert "potato" in doc
+    # Round-trip
+    assert parse(doc.as_string())["fruit"][0]["apple"]["texture"]["smooth"] is True
+
+
+def test_aot_extension_deep_merges_existing_nested_table() -> None:
+    content = """\
+[[fruit]]
+apple.texture.rough = false
+
+[potato]
+
+[fruit.apple.texture]
+smooth = true
+"""
+    texture = parse(content)["fruit"][0]["apple"]["texture"]
+    assert texture["rough"] is False
+    assert texture["smooth"] is True
+
+
+@pytest.mark.parametrize(
+    "content",
+    [
+        """\
+[[fruit]]
+apple.texture = "rough"
+
+[potato]
+
+[fruit.apple.texture]
+smooth = true
+""",
+        """\
+[[fruit]]
+apple.texture.smooth = false
+
+[potato]
+
+[fruit.apple.texture.smooth]
+value = true
+""",
+    ],
+)
+def test_aot_extension_keeps_redefinition_errors(content: str) -> None:
+    with pytest.raises(tomlkit.exceptions.ParseError, match=r'Key ".*" already exists'):
+        parse(content)
+
+
 def test_out_of_order_tables_are_still_dicts() -> None:
     content = """
 [a.a]
diff --git a/tomlkit/container.py b/tomlkit/container.py
index 75e0901..3a582aa 100644
--- a/tomlkit/container.py
+++ b/tomlkit/container.py
@@ -260,6 +260,37 @@ def append(
                     return self
                 elif isinstance(current, AoT):
                     if not item.is_aot_element():
+                        if item.is_super_table():
+                            # A dotted-key header like [fruit.apple.texture]
+                            # appearing after an unrelated table extends the last
+                            # element of the AoT (TOML spec: the [[fruit]]
+                            # header preceding the dotted key is implied).
+                            # Walk the super-table and merge into the last
+                            # element, bypassing the normal append path which
+                            # would trip over raw_append-created keys (they lack
+                            # the _dotted flag that _handle_dotted_key sets).
+                            def _deep_merge_into(
+                                target: Container, source: Table
+                            ) -> None:
+                                for sk, sv in source.value.body:
+                                    if sk is None:
+                                        continue
+                                    if sk in target:
+                                        existing = target.item(sk)
+                                        if isinstance(existing, Table) and isinstance(
+                                            sv, Table
+                                        ):
+                                            _deep_merge_into(
+                                                existing.value,
+                                                sv,  # type: ignore[arg-type]
+                                            )
+                                        else:
+                                            raise KeyAlreadyPresent(sk)
+                                    else:
+                                        target._raw_append(sk, sv)
+
+                            _deep_merge_into(current[-1].value, item)
+                            return self
                         # Tried to define a table after an AoT with the same name.
                         raise KeyAlreadyPresent(key)