diff --git a/src/axolotl/cli/config.py b/src/axolotl/cli/config.py
index 986167f02..b6f79c74c 100644
--- a/src/axolotl/cli/config.py
+++ b/src/axolotl/cli/config.py
@@ -5,7 +5,7 @@ import os
 import tempfile
 from pathlib import Path
 from tempfile import NamedTemporaryFile
-from typing import Union
+from typing import Any, Optional, Union
 from urllib.parse import urlparse
 
 import requests
@@ -32,6 +32,63 @@ from axolotl.utils.wandb_ import setup_wandb_env_vars
 
 LOG = get_logger(__name__)
 
+
+def _coerce_value(value: Any, existing: Optional[Any] = None) -> Any:
+    """Coerce a string CLI value to its most likely Python type.
+
+    If an existing value is present in the config, its type is used to guide
+    casting.  Otherwise, YAML-style inference is applied: booleans, ints,
+    floats, and None literals are recognised automatically.
+
+    Args:
+        value: The raw value (typically a string from the CLI).
+        existing: An optional existing config value whose type guides coercion.
+
+    Returns:
+        The value cast to the inferred or expected type.
+    """
+    if not isinstance(value, str):
+        return value
+
+    # If the config already has a typed value, cast to match
+    if existing is not None:
+        if isinstance(existing, bool):
+            return value.lower() in ("true", "1", "yes")
+        if isinstance(existing, int):
+            try:
+                return int(value)
+            except (ValueError, TypeError):
+                return value
+        if isinstance(existing, float):
+            try:
+                return float(value)
+            except (ValueError, TypeError):
+                return value
+        # For other types (str, list, dict, etc.), return as-is
+        return value
+
+    # No existing value -- use YAML-style inference
+    lower = value.lower()
+    if lower in ("true", "yes"):
+        return True
+    if lower in ("false", "no"):
+        return False
+    if lower in ("null", "none", "~"):
+        return None
+
+    # Try int then float
+    try:
+        return int(value)
+    except ValueError:
+        pass
+    try:
+        return float(value)
+    except ValueError:
+        pass
+
+    return value
+
+
 API_KEY_FIELDS = {"comet_api_key"}
 
 TELEMETRY_MANAGER = TelemetryManager.get_instance()
@@ -208,13 +265,37 @@ def load_cfg(
     # If there are any options passed in the cli, if it is something that seems valid
     # from the yaml, then overwrite the value
     cfg_keys = cfg.keys()
+
+    # Separate nested (dot-notation) kwargs from flat kwargs
+    nested_kwargs: dict[str, dict[str, Any]] = {}
+    flat_kwargs: dict[str, Any] = {}
     for key, value in kwargs.items():
+        if "__" in key:
+            parent, child = key.split("__", 1)
+            nested_kwargs.setdefault(parent, {})[child] = value
+        else:
+            flat_kwargs[key] = value
+
+    # Apply flat kwargs
+    for key, value in flat_kwargs.items():
         # If not strict, allow writing to cfg even if it's not in the yml already
         if key in cfg_keys or not cfg.strict:
-            if isinstance(cfg[key], bool):
-                cfg[key] = bool(value)
-            else:
-                cfg[key] = value
+            cfg[key] = _coerce_value(value, cfg.get(key))
+
+    # Apply nested kwargs (e.g., trl__beta -> cfg.trl.beta)
+    for parent, children in nested_kwargs.items():
+        if parent not in cfg_keys and cfg.strict:
+            continue
+        if cfg[parent] is None:
+            cfg[parent] = {}
+        if not isinstance(cfg[parent], dict):
+            LOG.warning(
+                "Overwriting non-dict value for '%s' with nested CLI overrides", parent
+            )
+            cfg[parent] = {}
+        for child_key, child_value in children.items():
+            existing_child = cfg[parent].get(child_key)
+            cfg[parent][child_key] = _coerce_value(child_value, existing_child)
 
     try:
         device_props = torch.cuda.get_device_properties("cuda")
diff --git a/src/axolotl/cli/utils/args.py b/src/axolotl/cli/utils/args.py
index 0aec737b8..d50a9163a 100644
--- a/src/axolotl/cli/utils/args.py
+++ b/src/axolotl/cli/utils/args.py
@@ -2,7 +2,7 @@
 
 import dataclasses
 from functools import wraps
-from types import NoneType
+from types import NoneType, UnionType
 from typing import Any, Callable, Type, Union, get_args, get_origin
 
 import click
@@ -20,7 +20,8 @@ def _strip_optional_type(field_type: type | str | None):
         If the input type is `Union[T, None]` or `Optional[T]`, returns `T`. Otherwise
             returns the input type unchanged.
     """
-    if get_origin(field_type) is Union and type(None) in get_args(field_type):
+    is_union = get_origin(field_type) is Union or isinstance(field_type, UnionType)
+    if is_union and type(None) in get_args(field_type):
         field_type = next(
             t for t in get_args(field_type) if not isinstance(t, NoneType)
         )
@@ -87,10 +88,70 @@ def add_options_from_dataclass(config_class: Type[Any]) -> Callable:
     return decorator
 
 
+def _is_pydantic_model(field_type: type) -> bool:
+    """Check if a type is a Pydantic BaseModel subclass."""
+    try:
+        return isinstance(field_type, type) and issubclass(field_type, BaseModel)
+    except TypeError:
+        return False
+
+
+def _get_field_description(field) -> str | None:
+    """Get description from a Pydantic field, checking both .description and json_schema_extra."""
+    if field.description:
+        return field.description
+    if field.json_schema_extra and isinstance(field.json_schema_extra, dict):
+        return field.json_schema_extra.get("description")
+    return None
+
+
+def _add_nested_model_options(
+    function: Callable, parent_name: str, model_class: Type[BaseModel]
+) -> Callable:
+    """
+    Add Click options for all fields of a nested Pydantic model using dot-notation.
+
+    Note: Only single-level nesting is supported (e.g., ``--trl.beta``).
+    Deeper nesting (e.g., ``--trl.scheduler.warmup``) is not handled.
+
+    Args:
+        function: Click command function to add options to.
+        parent_name: Parent field name (e.g., "trl").
+        model_class: Nested Pydantic model class.
+
+    Returns:
+        Function with added Click options.
+    """
+    for sub_name, sub_field in reversed(model_class.model_fields.items()):
+        sub_type = _strip_optional_type(sub_field.annotation)
+        # Use dot notation: --parent.sub_field
+        cli_name = f"{parent_name}.{sub_name}".replace("_", "-")
+        # The kwarg name uses double-underscore as separator
+        param_name = f"{parent_name}__{sub_name}"
+        description = _get_field_description(sub_field)
+
+        if sub_type is bool:
+            option_name = f"--{cli_name}/--no-{cli_name}"
+            function = click.option(
+                option_name, param_name, default=None, help=description
+            )(function)
+        else:
+            option_name = f"--{cli_name}"
+            click_type = {str: str, int: int, float: float}.get(sub_type)
+            function = click.option(
+                option_name, param_name, default=None, type=click_type, help=description
+            )(function)
+
+    return function
+
+
 def add_options_from_config(config_class: Type[BaseModel]) -> Callable:
     """
     Create Click options from the fields of a Pydantic model.
 
+    For fields whose type is itself a Pydantic BaseModel, dot-notation CLI options are
+    generated for each sub-field (e.g., ``--trl.beta=0.1``).
+
     Args:
         config_class: PyDantic model with fields to parse from the CLI
 
@@ -103,6 +164,11 @@ def add_options_from_config(config_class: Type[BaseModel]) -> Callable:
         for name, field in reversed(config_class.model_fields.items()):
             field_type = _strip_optional_type(field.annotation)
 
+            # Handle nested Pydantic models with dot-notation options
+            if _is_pydantic_model(field_type):
+                function = _add_nested_model_options(function, name, field_type)
+                continue
+
             if field_type is bool:
                 field_name = name.replace("_", "-")
                 option_name = f"--{field_name}/--no-{field_name}"
diff --git a/tests/cli/test_nested_options.py b/tests/cli/test_nested_options.py
new file mode 100644
index 000000000..221de951e
--- /dev/null
+++ b/tests/cli/test_nested_options.py
@@ -0,0 +1,227 @@
+"""Tests for nested config option handling via CLI dot-notation."""
+
+import click
+from click.testing import CliRunner
+from pydantic import BaseModel, Field
+
+from axolotl.cli.utils.args import add_options_from_config, filter_none_kwargs
+
+
+class InnerConfig(BaseModel):
+    """A nested config model for testing."""
+
+    beta: float | None = Field(
+        default=None,
+        description="Beta parameter.",
+    )
+    host: str | None = Field(
+        default=None,
+        description="Server host.",
+    )
+    use_feature: bool = Field(
+        default=False,
+        description="Whether to use the feature.",
+    )
+
+
+class OuterConfig(BaseModel):
+    """A top-level config model for testing."""
+
+    learning_rate: float | None = Field(
+        default=None,
+        description="Learning rate.",
+    )
+    inner: InnerConfig | None = Field(
+        default=None,
+        description="Inner config.",
+    )
+    name: str | None = Field(
+        default=None,
+        description="Model name.",
+    )
+
+
+class TestAddOptionsFromConfigNested:
+    """Test that add_options_from_config handles nested BaseModel fields."""
+
+    def setup_method(self):
+        self.runner = CliRunner()
+
+    def test_nested_dot_notation_options_are_registered(self):
+        """Nested model fields should create --parent.child CLI options."""
+
+        @click.command()
+        @add_options_from_config(OuterConfig)
+        @filter_none_kwargs
+        def cmd(**kwargs):
+            for k, v in sorted(kwargs.items()):
+                click.echo(f"{k}={v}")
+
+        result = self.runner.invoke(cmd, ["--inner.beta=0.5", "--inner.host=localhost"])
+        assert result.exit_code == 0, result.output
+        assert "inner__beta=0.5" in result.output
+        assert "inner__host=localhost" in result.output
+
+    def test_nested_bool_option(self):
+        """Nested bool fields should support --parent.field/--no-parent.field."""
+
+        @click.command()
+        @add_options_from_config(OuterConfig)
+        @filter_none_kwargs
+        def cmd(**kwargs):
+            for k, v in sorted(kwargs.items()):
+                click.echo(f"{k}={v}")
+
+        result = self.runner.invoke(cmd, ["--inner.use-feature"])
+        assert result.exit_code == 0, result.output
+        assert "inner__use_feature=True" in result.output
+
+    def test_flat_and_nested_options_together(self):
+        """Flat and nested options should work together."""
+
+        @click.command()
+        @add_options_from_config(OuterConfig)
+        @filter_none_kwargs
+        def cmd(**kwargs):
+            for k, v in sorted(kwargs.items()):
+                click.echo(f"{k}={v}")
+
+        result = self.runner.invoke(
+            cmd, ["--learning-rate=0.001", "--inner.beta=0.1", "--name=test"]
+        )
+        assert result.exit_code == 0, result.output
+        assert "learning_rate=0.001" in result.output
+        assert "inner__beta=0.1" in result.output
+        assert "name=test" in result.output
+
+    def test_no_nested_options_passed(self):
+        """When no nested options are passed, they should not appear in kwargs."""
+
+        @click.command()
+        @add_options_from_config(OuterConfig)
+        @filter_none_kwargs
+        def cmd(**kwargs):
+            click.echo(f"keys={sorted(kwargs.keys())}")
+
+        result = self.runner.invoke(cmd, ["--learning-rate=0.01"])
+        assert result.exit_code == 0, result.output
+        assert "inner__" not in result.output
+
+
+class TestLoadCfgNestedKwargs:
+    """Test that load_cfg correctly applies nested (double-underscore) kwargs."""
+
+    @staticmethod
+    def _apply_nested_kwargs(cfg, kwargs):
+        """Helper that mirrors the nested kwargs handling from load_cfg,
+        including type coercion for string CLI values."""
+        from axolotl.cli.config import _coerce_value
+
+        nested_kwargs: dict = {}
+        flat_kwargs: dict = {}
+        for key, value in kwargs.items():
+            if "__" in key:
+                parent, child = key.split("__", 1)
+                nested_kwargs.setdefault(parent, {})[child] = value
+            else:
+                flat_kwargs[key] = value
+
+        cfg_keys = cfg.keys()
+        for key, value in flat_kwargs.items():
+            if key in cfg_keys:
+                cfg[key] = _coerce_value(value, cfg.get(key))
+
+        for parent, children in nested_kwargs.items():
+            if cfg[parent] is None:
+                cfg[parent] = {}
+            if not isinstance(cfg[parent], dict):
+                cfg[parent] = {}
+            for child_key, child_value in children.items():
+                existing = cfg[parent].get(child_key)
+                cfg[parent][child_key] = _coerce_value(child_value, existing)
+
+        return cfg
+
+    def test_nested_kwargs_applied_to_cfg(self, tmp_path):
+        """Double-underscore kwargs should set nested config values."""
+        from axolotl.utils.dict import DictDefault
+
+        cfg = DictDefault({"trl": {"beta": 0.1}, "learning_rate": 0.01})
+        # CLI passes strings, so simulate that
+        kwargs = {
+            "trl__beta": "0.5",
+            "trl__host": "192.168.1.1",
+            "learning_rate": "0.02",
+        }
+
+        cfg = self._apply_nested_kwargs(cfg, kwargs)
+
+        assert cfg["learning_rate"] == 0.02
+        assert isinstance(cfg["learning_rate"], float)
+        assert cfg["trl"]["beta"] == 0.5
+        assert isinstance(cfg["trl"]["beta"], float)
+        assert cfg["trl"]["host"] == "192.168.1.1"
+
+    def test_nested_kwargs_creates_parent_if_none(self):
+        """If the parent key is None, nested kwargs should create the dict."""
+        from axolotl.utils.dict import DictDefault
+
+        cfg = DictDefault({"trl": None, "learning_rate": 0.01})
+        cfg = self._apply_nested_kwargs(cfg, {"trl__beta": "0.5"})
+
+        # No existing value, YAML-style inference: "0.5" -> 0.5
+        assert cfg["trl"]["beta"] == 0.5
+        assert isinstance(cfg["trl"]["beta"], float)
+
+    def test_nested_kwargs_overwrites_string_parent(self):
+        """If the parent key is a string, it should be replaced with a dict."""
+        from axolotl.utils.dict import DictDefault
+
+        cfg = DictDefault({"trl": "some_string", "learning_rate": 0.01})
+        cfg = self._apply_nested_kwargs(cfg, {"trl__beta": "0.5"})
+
+        assert cfg["trl"]["beta"] == 0.5
+
+
+class TestCoerceValue:
+    """Test YAML-style type coercion for CLI string values."""
+
+    def test_coerce_with_existing_float(self):
+        from axolotl.cli.config import _coerce_value
+
+        assert _coerce_value("0.5", 0.1) == 0.5
+        assert isinstance(_coerce_value("0.5", 0.1), float)
+
+    def test_coerce_with_existing_int(self):
+        from axolotl.cli.config import _coerce_value
+
+        assert _coerce_value("42", 10) == 42
+        assert isinstance(_coerce_value("42", 10), int)
+
+    def test_coerce_with_existing_bool(self):
+        from axolotl.cli.config import _coerce_value
+
+        assert _coerce_value("true", False) is True
+        assert _coerce_value("false", True) is False
+        assert _coerce_value("1", False) is True
+        assert _coerce_value("0", True) is False
+
+    def test_coerce_yaml_inference_no_existing(self):
+        """Without an existing value, use YAML-style inference."""
+        from axolotl.cli.config import _coerce_value
+
+        assert _coerce_value("true", None) is True
+        assert _coerce_value("false", None) is False
+        assert _coerce_value("42", None) == 42
+        assert isinstance(_coerce_value("42", None), int)
+        assert _coerce_value("3.14", None) == 3.14
+        assert isinstance(_coerce_value("3.14", None), float)
+        assert _coerce_value("null", None) is None
+        assert _coerce_value("hello", None) == "hello"
+
+    def test_coerce_non_string_passthrough(self):
+        """Non-string values should pass through unchanged."""
+        from axolotl.cli.config import _coerce_value
+
+        assert _coerce_value(0.5, 0.1) == 0.5
+        assert _coerce_value(True, False) is True