diff --git a/.chronus/changes/python-docstring-guideline-checks-2026-7-14-11-30-0.md b/.chronus/changes/python-docstring-guideline-checks-2026-7-14-11-30-0.md
new file mode 100644
index 00000000000..a2ca29b89fc
--- /dev/null
+++ b/.chronus/changes/python-docstring-guideline-checks-2026-7-14-11-30-0.md
@@ -0,0 +1,8 @@
+---
+# Change versionKind to one of: internal, fix, dependencies, feature, deprecation, breaking
+changeKind: fix
+packages:
+  - "@typespec/http-client-python"
+---
+
+[Python] Generate model/client/config docstrings and targeted pylint suppressions that satisfy the updated `azure-pylint-guidelines-checker` docstring checks (`docstring-keyword-should-match-keyword-only`, `docstring-missing-param`)
diff --git a/.chronus/changes/vnext-bump-2026-6-7-22-13-32.md b/.chronus/changes/vnext-bump-2026-6-7-22-13-32.md
new file mode 100644
index 00000000000..3abfe412b05
--- /dev/null
+++ b/.chronus/changes/vnext-bump-2026-6-7-22-13-32.md
@@ -0,0 +1,8 @@
+---
+# Change versionKind to one of: internal, fix, dependencies, feature, deprecation, breaking
+changeKind: dependencies
+packages:
+  - "@typespec/http-client-python"
+---
+
+[Python] Bump tool version targets: pylint 4.0.6, mypy 2.1.0, pyright 1.1.411, azure-pylint-guidelines-checker 0.5.8
diff --git a/packages/http-client-python/eng/scripts/ci/config/pylintrc b/packages/http-client-python/eng/scripts/ci/config/pylintrc
index 387021335fc..b6d3d4604cc 100644
--- a/packages/http-client-python/eng/scripts/ci/config/pylintrc
+++ b/packages/http-client-python/eng/scripts/ci/config/pylintrc
@@ -16,8 +16,12 @@ enable=useless-suppression
 # cyclic-import: because of https://github.com/PyCQA/pylint/issues/850
 # too-many-arguments: Due to the nature of the CLI many commands have large arguments set which reflect in large arguments set in corresponding methods.
 # too-many-lines: Due to code generation many files end up with too many lines.
+# no-cross-package-private-import: The guideline checker does not resolve relative
+#   imports (it ignores the import level), so legitimate same-package relative imports
+#   like `from ...operations._operations import ...` in generated async code are
+#   misreported as cross-package private imports.
 # Let's black deal with bad-continuation
-disable=missing-docstring,locally-disabled,fixme,cyclic-import,too-many-arguments,invalid-name,duplicate-code,too-few-public-methods,consider-using-f-string,super-with-arguments,redefined-builtin,import-outside-toplevel,client-suffix-needed,unnecessary-dunder-call,unnecessary-ellipsis,disallowed-name,consider-using-max-builtin,unknown-option-value,file-needs-copyright-header,too-many-positional-arguments
+disable=missing-docstring,locally-disabled,fixme,cyclic-import,too-many-arguments,invalid-name,duplicate-code,too-few-public-methods,consider-using-f-string,super-with-arguments,redefined-builtin,import-outside-toplevel,client-suffix-needed,unnecessary-dunder-call,unnecessary-ellipsis,disallowed-name,consider-using-max-builtin,unknown-option-value,file-needs-copyright-header,too-many-positional-arguments,no-cross-package-private-import
 
 [FORMAT]
 max-line-length=120
diff --git a/packages/http-client-python/eng/scripts/ci/dev_requirements.txt b/packages/http-client-python/eng/scripts/ci/dev_requirements.txt
index adfd8faac20..a52b260b058 100644
--- a/packages/http-client-python/eng/scripts/ci/dev_requirements.txt
+++ b/packages/http-client-python/eng/scripts/ci/dev_requirements.txt
@@ -1,8 +1,8 @@
-pyright==1.1.407
-pylint==4.0.4
+pyright==1.1.411
+pylint==4.0.6
 tox==4.16.0
 tox-uv
-mypy==1.19.1
+mypy==2.1.0
 colorama==0.4.6
 debugpy==1.8.2
 pytest==9.0.3
diff --git a/packages/http-client-python/generator/pygen/codegen/models/client.py b/packages/http-client-python/generator/pygen/codegen/models/client.py
index abb4d83c49d..82bdcdf1508 100644
--- a/packages/http-client-python/generator/pygen/codegen/models/client.py
+++ b/packages/http-client-python/generator/pygen/codegen/models/client.py
@@ -53,6 +53,17 @@ def description(self) -> str:
     def name(self) -> str:
         return self.yaml_data["name"]
 
+    @property
+    def has_docstring_only_keyword(self) -> bool:
+        """Whether the constructor docstring documents a ``:keyword:`` that is not a real
+        keyword-only argument (it is popped from ``kwargs`` instead).
+
+        This happens for params routed to ``**kwargs`` (e.g. ``api_version``): they are
+        still rendered as ``:keyword:`` in the docstring, so we must silence the
+        ``docstring-keyword-should-match-keyword-only`` guideline check.
+        """
+        return any(p for p in self.parameters.method if p.method_location == ParameterMethodLocation.KWARG)
+
 
 class Client(_ClientConfigBase[ClientGlobalParameterList]):
     """Model representing our service client"""
@@ -187,6 +198,8 @@ def pylint_disable(self) -> str:
             retval = add_to_pylint_disable(retval, "too-many-instance-attributes")
         if len(self.name) > NAME_LENGTH_LIMIT:
             retval = add_to_pylint_disable(retval, "name-too-long")
+        if self.has_docstring_only_keyword or self.has_public_lro_operations:
+            retval = add_to_pylint_disable(retval, "docstring-keyword-should-match-keyword-only")
         return retval
 
     @property
@@ -375,6 +388,8 @@ def pylint_disable(self) -> str:
         retval = add_to_pylint_disable("", "too-many-instance-attributes") if self.code_model.is_azure_flavor else ""
         if len(self.name) > NAME_LENGTH_LIMIT:
             retval = add_to_pylint_disable(retval, "name-too-long")
+        if self.has_docstring_only_keyword:
+            retval = add_to_pylint_disable(retval, "docstring-keyword-should-match-keyword-only")
         return retval
 
     @property
diff --git a/packages/http-client-python/generator/pygen/codegen/models/operation_group.py b/packages/http-client-python/generator/pygen/codegen/models/operation_group.py
index 5c0f467806c..798c7ae5b96 100644
--- a/packages/http-client-python/generator/pygen/codegen/models/operation_group.py
+++ b/packages/http-client-python/generator/pygen/codegen/models/operation_group.py
@@ -82,6 +82,8 @@ def pylint_disable(self) -> str:
         retval: str = ""
         if self.has_abstract_operations:
             retval = add_to_pylint_disable(retval, "abstract-class-instantiated")
+        if not self.is_mixin:
+            retval = add_to_pylint_disable(retval, "docstring-missing-param")
         if len(self.operations) > 20:
             retval = add_to_pylint_disable(retval, "too-many-public-methods")
         if len(self.class_name) > NAME_LENGTH_LIMIT and self.class_name[0] != "_":
diff --git a/packages/http-client-python/generator/pygen/codegen/serializers/model_serializer.py b/packages/http-client-python/generator/pygen/codegen/serializers/model_serializer.py
index 87a0b2cc4aa..15e82108a89 100644
--- a/packages/http-client-python/generator/pygen/codegen/serializers/model_serializer.py
+++ b/packages/http-client-python/generator/pygen/codegen/serializers/model_serializer.py
@@ -23,7 +23,7 @@
 )
 from .import_serializer import FileImportSerializer
 from .base_serializer import BaseSerializer
-from ..models.utils import NamespaceType
+from ..models.utils import NamespaceType, add_to_pylint_disable
 
 
 def _get_xml_deserializer_name(prop: Property) -> Optional[str]:  # pylint: disable=too-many-return-statements
@@ -122,6 +122,15 @@ def input_documentation_string(prop: Property) -> list[str]:
         # building the param line of the property doc
         return _documentation_string(prop, "keyword", "paramtype")
 
+    def keyword_documentation_string(self, model: ModelType) -> list[str]:
+        # building the ``:keyword:``/``:paramtype:`` lines for the keyword-only
+        # arguments of the generated ``__init__`` overload so that the docstring
+        # keeps a 1:1 correlation with the keyword-only arguments in the signature.
+        retval: list[str] = []
+        for prop in sorted(self._init_line_parameters(model), key=lambda x: x.optional):
+            retval.extend(self.input_documentation_string(prop))
+        return retval
+
     @staticmethod
     def variable_documentation_string(prop: Property) -> list[str]:
         return _documentation_string(prop, "ivar", "vartype")
@@ -199,6 +208,16 @@ def pylint_disable_items(self, model: ModelType) -> list[str]:
     def pylint_disable(self, model: ModelType) -> str:
         return "  # pylint: disable=" + ", ".join(self.pylint_disable_items(model))
 
+    def class_pylint_disable(self, model: ModelType) -> str:
+        """Class-level pylint disables for the model declaration line."""
+        retval = model.pylint_disable()
+        # When the model's only constructor is ``def __init__(self, *args, **kwargs)`` (i.e. no
+        # typed overload is generated), the guideline checker reports the ``*args`` vararg as an
+        # undocumented param. There is no meaningful param to document, so silence the check.
+        if not self.need_init(model) and self.initialize_properties(model):
+            retval = add_to_pylint_disable(retval, "docstring-missing-param")
+        return retval
+
     def global_pylint_disables(self) -> str:
         return ""
 
@@ -244,7 +263,7 @@ def declare_model(self, model: ModelType) -> str:
         )
         if model.parents:
             basename = ", ".join([m.name for m in model.parents])
-        return f"class {model.name}({basename}):{model.pylint_disable()}"
+        return f"class {model.name}({basename}):{self.class_pylint_disable(model)}"
 
     @staticmethod
     def get_properties_to_initialize(model: ModelType) -> list[Property]:
@@ -407,7 +426,7 @@ def declare_model(self, model: ModelType) -> str:
             basename = ", ".join([m.name for m in model.parents])
         if model.discriminator_value:
             basename += f", discriminator='{model.discriminator_value}'"
-        return f"class {model.name}({basename}):{model.pylint_disable()}"
+        return f"class {model.name}({basename}):{self.class_pylint_disable(model)}"
 
     @staticmethod
     def get_properties_to_declare(model: ModelType) -> list[Property]:
diff --git a/packages/http-client-python/generator/pygen/codegen/templates/model_base.py.jinja2 b/packages/http-client-python/generator/pygen/codegen/templates/model_base.py.jinja2
index e51a7645dde..40fde9fa098 100644
--- a/packages/http-client-python/generator/pygen/codegen/templates/model_base.py.jinja2
+++ b/packages/http-client-python/generator/pygen/codegen/templates/model_base.py.jinja2
@@ -161,7 +161,15 @@ def _is_readonly(p):
 
 
 class SdkJSONEncoder(JSONEncoder):
-    """A JSON encoder that's capable of serializing datetime objects and bytes."""
+    """A JSON encoder that's capable of serializing datetime objects and bytes.
+
+    :param args: Additional positional arguments passed to the base ``JSONEncoder``.
+    :type args: typing.Any
+    :keyword exclude_readonly: Whether to exclude readonly properties. Defaults to False.
+    :paramtype exclude_readonly: bool
+    :keyword format: The format to use for serialization. Defaults to None.
+    :paramtype format: typing.Optional[str]
+    """
 
     def __init__(self, *args, exclude_readonly: bool = False, format: typing.Optional[str] = None, **kwargs):
         super().__init__(*args, **kwargs)
diff --git a/packages/http-client-python/generator/pygen/codegen/templates/model_dpg.py.jinja2 b/packages/http-client-python/generator/pygen/codegen/templates/model_dpg.py.jinja2
index 8bcbbf4af41..6a2b533ae55 100644
--- a/packages/http-client-python/generator/pygen/codegen/templates/model_dpg.py.jinja2
+++ b/packages/http-client-python/generator/pygen/codegen/templates/model_dpg.py.jinja2
@@ -16,6 +16,11 @@
             {% endfor %}
         {% endfor %}
     {% endif %}
+    {% if serializer.need_init(model) %}
+        {% for line in serializer.keyword_documentation_string(model) %}
+    {{ macros.wrap_model_string(line, '\n    ') -}}
+        {% endfor %}
+    {% endif %}
     """
 
     {% if model.is_polymorphic %}
diff --git a/packages/http-client-python/generator/pygen/codegen/templates/serialization.py.jinja2 b/packages/http-client-python/generator/pygen/codegen/templates/serialization.py.jinja2
index 65a9c1f8f9e..8194e5c1566 100644
--- a/packages/http-client-python/generator/pygen/codegen/templates/serialization.py.jinja2
+++ b/packages/http-client-python/generator/pygen/codegen/templates/serialization.py.jinja2
@@ -476,7 +476,11 @@ def _decode_attribute_map_key(key):
 
 
 class Serializer:  # pylint: disable=too-many-public-methods
-    """Request object model serializer."""
+    """Request object model serializer.
+
+    :param classes: Mapping of model names to model types, used to resolve models during serialization.
+    :type classes: typing.Optional[typing.Mapping[str, type]]
+    """
 
     basic_types = {str: "str", int: "int", bool: "bool", float: "float"}
 
diff --git a/packages/http-client-python/tests/tox.ini b/packages/http-client-python/tests/tox.ini
index a94a60603e4..ecdc52886ba 100644
--- a/packages/http-client-python/tests/tox.ini
+++ b/packages/http-client-python/tests/tox.ini
@@ -69,7 +69,7 @@ deps =
     -r {tox_root}/requirements/azure.txt
     -e {tox_root}/../generator
 commands =
-    uv pip install azure-pylint-guidelines-checker==0.5.2 --index-url="https://pkgs.dev.azure.com/azure-sdk/public/_packaging/azure-sdk-for-python/pypi/simple/"
+    uv pip install azure-pylint-guidelines-checker==0.5.8 --index-url="https://pkgs.dev.azure.com/azure-sdk/public/_packaging/azure-sdk-for-python/pypi/simple/"
     python {tox_root}/install_packages.py azure {tox_root}
     python {tox_root}/../eng/scripts/ci/run_pylint.py -t azure -s generated {posargs}