diff --git a/src/tyro/_parsers.py b/src/tyro/_parsers.py
index ef6bf013..22802113 100644
--- a/src/tyro/_parsers.py
+++ b/src/tyro/_parsers.py
@@ -145,7 +145,9 @@ def from_callable_or_type(
                     )
 
                 # Helptext for this field; used as description for grouping arguments.
-                class_field_name = _strings.make_field_name([field.intern_name])
+                class_field_name = _strings.make_field_name(
+                    [intern_prefix, field.intern_name]
+                )
                 if field.helptext is not None:
                     helptext_from_intern_prefixed_field_name[class_field_name] = (
                         field.helptext
@@ -235,10 +237,20 @@ def apply_args(
         """Create defined arguments and subparsers."""
 
         # Make argument groups.
-        def format_group_name(prefix: str) -> str:
-            return (prefix + " options").strip()
+        def format_group_name(group_name: str) -> str:
+            return (group_name + " options").strip()
+
+        def group_name_from_arg(arg: _arguments.ArgumentDefinition) -> str:
+            prefix = arg.lowered.name_or_flag
+            if prefix.startswith("--"):
+                prefix = prefix[2:]
+            if "." in prefix:
+                prefix = prefix.rpartition(".")[0]
+            else:
+                prefix = ""
+            return prefix
 
-        group_from_prefix: Dict[str, argparse._ArgumentGroup] = {
+        group_from_group_name: Dict[str, argparse._ArgumentGroup] = {
             "": parser._action_groups[1],
             **{
                 cast(str, group.title).partition(" ")[0]: group
@@ -251,9 +263,10 @@ def format_group_name(prefix: str) -> str:
         # Add each argument group. Note that groups with only suppressed arguments won't
         # be added.
         for arg in self.args:
+            group_name = group_name_from_arg(arg)
             if (
                 arg.lowered.help is not argparse.SUPPRESS
-                and arg.extern_prefix not in group_from_prefix
+                and group_name not in group_from_group_name
             ):
                 description = (
                     parent.helptext_from_intern_prefixed_field_name.get(
@@ -262,24 +275,23 @@ def format_group_name(prefix: str) -> str:
                     if parent is not None
                     else None
                 )
-                group_from_prefix[arg.extern_prefix] = parser.add_argument_group(
-                    format_group_name(arg.extern_prefix),
+                group_from_group_name[group_name] = parser.add_argument_group(
+                    format_group_name(group_name),
                     description=description,
                 )
 
-        # Add each argument.
-        for arg in self.args:
+            # Add each argument.
             if arg.field.is_positional():
                 arg.add_argument(positional_group)
                 continue
 
-            if arg.extern_prefix in group_from_prefix:
-                arg.add_argument(group_from_prefix[arg.extern_prefix])
+            if group_name in group_from_group_name:
+                arg.add_argument(group_from_group_name[group_name])
             else:
                 # Suppressed argument: still need to add them, but they won't show up in
                 # the helptext so it doesn't matter which group.
                 assert arg.lowered.help is argparse.SUPPRESS
-                arg.add_argument(group_from_prefix[""])
+                arg.add_argument(group_from_group_name[""])
 
         for child in self.child_from_prefix.values():
             child.apply_args(parser, parent=self)
diff --git a/tests/test_conf.py b/tests/test_conf.py
index 1750e8db..54dd9aa3 100644
--- a/tests/test_conf.py
+++ b/tests/test_conf.py
@@ -1497,8 +1497,8 @@ class DatasetConfig:
     with pytest.raises(SystemExit), contextlib.redirect_stdout(target):
         instantiate_dataclasses((OptimizerConfig, DatasetConfig), args=["--help"])
     helptext = target.getvalue()
-    assert "OptimizerConfig options" in helptext
-    assert "DatasetConfig options" in helptext
+    assert "OptimizerConfig options" not in helptext
+    assert "DatasetConfig options" not in helptext
 
 
 def test_counter_action() -> None:
diff --git a/tests/test_nested.py b/tests/test_nested.py
index f9a57c09..98ec5cb6 100644
--- a/tests/test_nested.py
+++ b/tests/test_nested.py
@@ -18,11 +18,17 @@ class B:
     class Nested:
         x: int
         b: B
+        """Helptext for b"""
 
     assert tyro.cli(Nested, args=["--x", "1", "--b.y", "3"]) == Nested(x=1, b=B(y=3))
     with pytest.raises(SystemExit):
         tyro.cli(Nested, args=["--x", "1"])
 
+    def main(x: Nested):
+        return x
+
+    assert "Helptext for b" in get_helptext_with_checks(main)
+
 
 def test_nested_annotated() -> None:
     @dataclasses.dataclass
diff --git a/tests/test_py311_generated/ok.py b/tests/test_py311_generated/ok.py
new file mode 100644
index 00000000..73e5b33b
--- /dev/null
+++ b/tests/test_py311_generated/ok.py
@@ -0,0 +1,12 @@
+from dataclasses import dataclass
+from typing import Literal
+
+import tyro
+
+
+@dataclass(frozen=True)
+class Container[T]:
+    a: T
+
+
+tyro.cli(Container[Container[bool] | Container[Literal["1", "2"]]])
diff --git a/tests/test_py311_generated/test_conf_generated.py b/tests/test_py311_generated/test_conf_generated.py
index 04301ed7..13997ecb 100644
--- a/tests/test_py311_generated/test_conf_generated.py
+++ b/tests/test_py311_generated/test_conf_generated.py
@@ -1492,8 +1492,8 @@ class DatasetConfig:
     with pytest.raises(SystemExit), contextlib.redirect_stdout(target):
         instantiate_dataclasses((OptimizerConfig, DatasetConfig), args=["--help"])
     helptext = target.getvalue()
-    assert "OptimizerConfig options" in helptext
-    assert "DatasetConfig options" in helptext
+    assert "OptimizerConfig options" not in helptext
+    assert "DatasetConfig options" not in helptext
 
 
 def test_counter_action() -> None:
diff --git a/tests/test_py311_generated/test_nested_generated.py b/tests/test_py311_generated/test_nested_generated.py
index 4ae8a4e7..5a611b42 100644
--- a/tests/test_py311_generated/test_nested_generated.py
+++ b/tests/test_py311_generated/test_nested_generated.py
@@ -28,11 +28,17 @@ class B:
     class Nested:
         x: int
         b: B
+        """Helptext for b"""
 
     assert tyro.cli(Nested, args=["--x", "1", "--b.y", "3"]) == Nested(x=1, b=B(y=3))
     with pytest.raises(SystemExit):
         tyro.cli(Nested, args=["--x", "1"])
 
+    def main(x: Nested):
+        return x
+
+    assert "Helptext for b" in get_helptext_with_checks(main)
+
 
 def test_nested_annotated() -> None:
     @dataclasses.dataclass
diff --git a/tests/test_py311_generated/test_pydantic_helptext_advanced_generated.py b/tests/test_py311_generated/test_pydantic_helptext_advanced_generated.py
new file mode 100644
index 00000000..a7da8acc
--- /dev/null
+++ b/tests/test_py311_generated/test_pydantic_helptext_advanced_generated.py
@@ -0,0 +1,98 @@
+"""Adapted from: https://github.com/brentyi/tyro/issues/183"""
+
+from typing import Annotated, NamedTuple, Set
+
+from helptext_utils import get_helptext_with_checks
+from pydantic import BaseModel, Field
+
+import tyro
+
+
+class MyRange(NamedTuple):
+    low: int
+    high: int
+
+    def __str__(self):
+        return f"<{self.low}, {self.high}>"
+
+    @staticmethod
+    def tyro_constructor(
+        range_str: Annotated[
+            str,
+            tyro.conf.arg(name=""),
+        ],
+    ):
+        import re
+
+        m = re.match("([0-9]+)(-([0-9]+))*", range_str)
+        low = m[1]  # type: ignore
+        high = low if not m[3] else m[3]  # type: ignore
+
+        return MyRange(int(low), int(high))
+
+    @staticmethod
+    def tyro_constructor_set(
+        range_str_set: Annotated[
+            Set[str],
+            tyro.conf.arg(name=""),
+        ],
+    ):
+        return {MyRange.tyro_constructor(r) for r in range_str_set}
+
+
+class MySpec(BaseModel):
+    some_set: Set[int] = Field(
+        default={1, 2, 3},
+        description="Some set of integers",
+        title="Some set",
+    )
+
+    some_string: str = Field(
+        description="Some string without a default value.", title="SomeSTR"
+    )
+
+    here_comes_the_trouble: Annotated[
+        Set[MyRange],
+        tyro.conf.arg(constructor=MyRange.tyro_constructor_set),
+    ] = Field(
+        default={MyRange(0, 1024)},
+        description="I would like this one in the same group as others",
+        title="Please help",
+    )
+
+
+def add_spec(spec: MySpec) -> MySpec:
+    return spec
+
+
+def test_functionality() -> None:
+    assert tyro.cli(
+        add_spec, args=["--spec.some-set", "1", "2", "3", "--spec.some-string", "hello"]
+    ) == MySpec(
+        some_set={1, 2, 3},
+        some_string="hello",
+        here_comes_the_trouble={MyRange(0, 1024)},
+    )
+    assert tyro.cli(
+        add_spec,
+        args=[
+            "--spec.some-set",
+            "1",
+            "2",
+            "3",
+            "--spec.some-string",
+            "hello",
+            "--spec.here-comes-the-trouble",
+            "0-512",
+        ],
+    ) == MySpec(
+        some_set={1, 2, 3},
+        some_string="hello",
+        here_comes_the_trouble={MyRange(0, 512)},
+    )
+
+
+def test_helptext() -> None:
+    helptext = get_helptext_with_checks(add_spec)
+    assert "spec options" in helptext
+    assert "spec.here-comes-the-trouble-options" not in helptext
diff --git a/tests/test_pydantic_helptext_advanced.py b/tests/test_pydantic_helptext_advanced.py
new file mode 100644
index 00000000..245a2150
--- /dev/null
+++ b/tests/test_pydantic_helptext_advanced.py
@@ -0,0 +1,99 @@
+"""Adapted from: https://github.com/brentyi/tyro/issues/183"""
+
+from typing import NamedTuple, Set
+
+from helptext_utils import get_helptext_with_checks
+from pydantic import BaseModel, Field
+from typing_extensions import Annotated
+
+import tyro
+
+
+class MyRange(NamedTuple):
+    low: int
+    high: int
+
+    def __str__(self):
+        return f"<{self.low}, {self.high}>"
+
+    @staticmethod
+    def tyro_constructor(
+        range_str: Annotated[
+            str,
+            tyro.conf.arg(name=""),
+        ],
+    ):
+        import re
+
+        m = re.match("([0-9]+)(-([0-9]+))*", range_str)
+        low = m[1]  # type: ignore
+        high = low if not m[3] else m[3]  # type: ignore
+
+        return MyRange(int(low), int(high))
+
+    @staticmethod
+    def tyro_constructor_set(
+        range_str_set: Annotated[
+            Set[str],
+            tyro.conf.arg(name=""),
+        ],
+    ):
+        return {MyRange.tyro_constructor(r) for r in range_str_set}
+
+
+class MySpec(BaseModel):
+    some_set: Set[int] = Field(
+        default={1, 2, 3},
+        description="Some set of integers",
+        title="Some set",
+    )
+
+    some_string: str = Field(
+        description="Some string without a default value.", title="SomeSTR"
+    )
+
+    here_comes_the_trouble: Annotated[
+        Set[MyRange],
+        tyro.conf.arg(constructor=MyRange.tyro_constructor_set),
+    ] = Field(
+        default={MyRange(0, 1024)},
+        description="I would like this one in the same group as others",
+        title="Please help",
+    )
+
+
+def add_spec(spec: MySpec) -> MySpec:
+    return spec
+
+
+def test_functionality() -> None:
+    assert tyro.cli(
+        add_spec, args=["--spec.some-set", "1", "2", "3", "--spec.some-string", "hello"]
+    ) == MySpec(
+        some_set={1, 2, 3},
+        some_string="hello",
+        here_comes_the_trouble={MyRange(0, 1024)},
+    )
+    assert tyro.cli(
+        add_spec,
+        args=[
+            "--spec.some-set",
+            "1",
+            "2",
+            "3",
+            "--spec.some-string",
+            "hello",
+            "--spec.here-comes-the-trouble",
+            "0-512",
+        ],
+    ) == MySpec(
+        some_set={1, 2, 3},
+        some_string="hello",
+        here_comes_the_trouble={MyRange(0, 512)},
+    )
+
+
+def test_helptext() -> None:
+    helptext = get_helptext_with_checks(add_spec)
+    assert "spec options" in helptext
+    assert "spec.here-comes-the-trouble-options" not in helptext