diff --git a/CHANGES/726.misc b/CHANGES/726.misc
new file mode 100644
index 000000000..6891eb427
--- /dev/null
+++ b/CHANGES/726.misc
@@ -0,0 +1 @@
+Adjusted to typing improvements in click>=8.1.4.
diff --git a/pulpcore/cli/ansible/content.py b/pulpcore/cli/ansible/content.py
index eba5d7f28..0525948e1 100644
--- a/pulpcore/cli/ansible/content.py
+++ b/pulpcore/cli/ansible/content.py
@@ -1,4 +1,4 @@
-from typing import IO, Any, Callable, Optional, Union
+from typing import IO, Any, Callable, Optional
 
 import click
 from pulp_glue.ansible.context import (
@@ -218,7 +218,9 @@ def content(ctx: click.Context, pulp_ctx: PulpCLIContext, content_type: str) ->
 content.add_command(show_command(decorators=lookup_options))
 
 
-@content.command()
+# This is a mypy bug getting confused with positional args
+# https://github.com/python/mypy/issues/15037
+@content.command()  # type: ignore [arg-type]
 @click.option("--file", type=click.File("rb"), required=True)
 @repository_option
 @pulp_option(
@@ -253,11 +255,7 @@ def content(ctx: click.Context, pulp_ctx: PulpCLIContext, content_type: str) ->
 @pass_pulp_context
 def upload(
     pulp_ctx: PulpCLIContext,
-    content_ctx: Union[
-        PulpAnsibleRoleContext,
-        PulpAnsibleCollectionVersionContext,
-        PulpAnsibleCollectionVersionSignatureContext,
-    ],
+    content_ctx: PulpEntityContext,
     file: IO[bytes],
     **kwargs: Any,
 ) -> None:
diff --git a/pulpcore/cli/ansible/distribution.py b/pulpcore/cli/ansible/distribution.py
index 852a79013..103181382 100644
--- a/pulpcore/cli/ansible/distribution.py
+++ b/pulpcore/cli/ansible/distribution.py
@@ -7,6 +7,7 @@
     EntityFieldDefinition,
     PluginRequirement,
     PulpContext,
+    PulpEntityContext,
 )
 from pulp_glue.common.i18n import get_translation
 
@@ -104,7 +105,7 @@ def distribution(ctx: click.Context, pulp_ctx: PulpContext, distribution_type: s
 @pulp_labels_option
 @pass_entity_context
 def update(
-    distribution_ctx: PulpAnsibleDistributionContext,
+    distribution_ctx: PulpEntityContext,
     base_path: Optional[str],
     repository: EntityFieldDefinition,
     content_guard: EntityFieldDefinition,
@@ -114,6 +115,8 @@ def update(
     """
     To remove repository or repository_version fields set --repository to ""
     """
+    assert isinstance(distribution_ctx, PulpAnsibleDistributionContext)
+
     dist_body: EntityDefinition = distribution_ctx.entity
     name: str = dist_body["name"]
     body: EntityDefinition = dict()
diff --git a/pulpcore/cli/common/config.py b/pulpcore/cli/common/config.py
index 731906973..f88502e5e 100644
--- a/pulpcore/cli/common/config.py
+++ b/pulpcore/cli/common/config.py
@@ -143,7 +143,9 @@ def config() -> None:
     pass
 
 
-@config.command(help=_("Create a pulp-cli config settings file"))
+# This is a mypy bug getting confused with positional args
+# https://github.com/python/mypy/issues/15037
+@config.command(help=_("Create a pulp-cli config settings file"))  # type: ignore [arg-type]
 @config_options
 @click.option("--interactive", "-i", is_flag=True)
 @click.option("--editor", "-e", is_flag=True, help=_("Edit the config file in an editor"))
diff --git a/pulpcore/cli/common/generic.py b/pulpcore/cli/common/generic.py
index fd8b636d1..5a49616b0 100644
--- a/pulpcore/cli/common/generic.py
+++ b/pulpcore/cli/common/generic.py
@@ -1,13 +1,12 @@
 import datetime
 import json
 import re
+import typing as t
 from functools import lru_cache, wraps
-from typing import IO, Any, Callable, Dict, Iterable, List, Mapping, Optional, Tuple, Type, Union
 
 import click
 import schema as s
 import yaml
-from click.decorators import FC, F
 from pulp_glue.common.context import (
     DATETIME_FORMATS,
     DEFAULT_LIMIT,
@@ -42,6 +41,10 @@
 _ = translation.gettext
 
 
+_AnyCallable = t.Callable[..., t.Any]
+FC = t.TypeVar("FC", bound=t.Union[_AnyCallable, click.Command])
+
+
 class IncompatibleContext(click.UsageError):
     pass
 
@@ -49,7 +52,7 @@ class IncompatibleContext(click.UsageError):
 class ClickNoWait(click.ClickException):
     exit_code = 0
 
-    def show(self, file: Optional[IO[str]] = None) -> None:
+    def show(self, file: t.Optional[t.IO[str]] = None) -> None:
         """
         Format the message into file or STDERR.
         Overwritten from base class to not print "Error: ".
@@ -60,7 +63,7 @@ def show(self, file: Optional[IO[str]] = None) -> None:
 
 
 class PulpJSONEncoder(json.JSONEncoder):
-    def default(self, obj: Any) -> Any:
+    def default(self, obj: t.Any) -> t.Any:
         if isinstance(obj, datetime.datetime):
             return obj.isoformat()
         else:
@@ -75,7 +78,7 @@ class PulpCLIContext(PulpContext):
     def __init__(
         self,
         api_root: str,
-        api_kwargs: Dict[str, Any],
+        api_kwargs: t.Dict[str, t.Any],
         background_tasks: bool,
         timeout: int,
         format: str,
@@ -93,10 +96,10 @@ def __init__(
     def echo(self, message: str, nl: bool = True, err: bool = False) -> None:
         click.echo(message, nl=nl, err=err)
 
-    def prompt(self, text: str, hide_input: bool = False) -> Any:
+    def prompt(self, text: str, hide_input: bool = False) -> t.Any:
         return click.prompt(text, hide_input=hide_input)
 
-    def output_result(self, result: Any) -> None:
+    def output_result(self, result: t.Any) -> None:
         """
         Dump the provided result to the console using the selected renderer
         """
@@ -124,16 +127,17 @@ def output_result(self, result: Any) -> None:
 
 pass_pulp_context = click.make_pass_decorator(PulpCLIContext)
 pass_entity_context = click.make_pass_decorator(PulpEntityContext)
+pass_acs_context = click.make_pass_decorator(PulpACSContext)
+pass_content_context = click.make_pass_decorator(PulpContentContext)
 pass_repository_context = click.make_pass_decorator(PulpRepositoryContext)
 pass_repository_version_context = click.make_pass_decorator(PulpRepositoryVersionContext)
-pass_content_context = click.make_pass_decorator(PulpContentContext)
 
 
 ##############################################################################
 # Custom types for parameters
 
 
-def int_or_empty(value: str) -> Union[str, int]:
+def int_or_empty(value: str) -> t.Union[str, int]:
     if value == "":
         return ""
     else:
@@ -143,7 +147,7 @@ def int_or_empty(value: str) -> Union[str, int]:
 int_or_empty.__name__ = "int or empty"
 
 
-def float_or_empty(value: str) -> Union[str, float]:
+def float_or_empty(value: str) -> t.Union[str, float]:
     if value == "":
         return ""
     else:
@@ -160,16 +164,16 @@ def float_or_empty(value: str) -> Union[str, float]:
 class PulpCommand(click.Command):
     def __init__(
         self,
-        *args: Any,
-        allowed_with_contexts: Optional[Tuple[Type[PulpEntityContext]]] = None,
-        needs_plugins: Optional[List[PluginRequirement]] = None,
-        **kwargs: Any,
+        *args: t.Any,
+        allowed_with_contexts: t.Optional[t.Tuple[t.Type[PulpEntityContext]]] = None,
+        needs_plugins: t.Optional[t.List[PluginRequirement]] = None,
+        **kwargs: t.Any,
     ):
         self.allowed_with_contexts = allowed_with_contexts
         self.needs_plugins = needs_plugins
         super().__init__(*args, **kwargs)
 
-    def invoke(self, ctx: click.Context) -> Any:
+    def invoke(self, ctx: click.Context) -> t.Any:
         try:
             if self.needs_plugins:
                 pulp_ctx = ctx.find_object(PulpCLIContext)
@@ -194,9 +198,9 @@ def format_help_text(
                 self.help = self.help.format(entity=entity_ctx.ENTITY, entities=entity_ctx.ENTITIES)
         super().format_help_text(ctx, formatter)
 
-    def get_params(self, ctx: click.Context) -> List[click.Parameter]:
+    def get_params(self, ctx: click.Context) -> t.List[click.Parameter]:
         params = super().get_params(ctx)
-        new_params: List[click.Parameter] = []
+        new_params: t.List[click.Parameter] = []
         for param in params:
             if isinstance(param, PulpOption):
                 if param.allowed_with_contexts is not None:
@@ -210,7 +214,7 @@ class PulpGroup(PulpCommand, click.Group):
     command_class = PulpCommand
     group_class = type
 
-    def get_command(self, ctx: click.Context, cmd_name: str) -> Optional[click.Command]:
+    def get_command(self, ctx: click.Context, cmd_name: str) -> t.Optional[click.Command]:
         # Overwriting this removes the command from the help message and from being callable
         cmd = super().get_command(ctx, cmd_name)
         if isinstance(cmd, (PulpCommand, PulpGroup)):
@@ -223,7 +227,7 @@ def get_command(self, ctx: click.Context, cmd_name: str) -> Optional[click.Comma
                     )
         return cmd
 
-    def list_commands(self, ctx: click.Context) -> List[str]:
+    def list_commands(self, ctx: click.Context) -> t.List[str]:
         commands_filtered_by_context = []
 
         for name, cmd in self.commands.items():
@@ -236,27 +240,31 @@ def list_commands(self, ctx: click.Context) -> List[str]:
         return sorted(commands_filtered_by_context)
 
 
-def pulp_command(name: Optional[str] = None, **kwargs: Any) -> Callable[[F], click.Command]:
+def pulp_command(
+    name: t.Optional[str] = None, **kwargs: t.Any
+) -> t.Callable[[_AnyCallable], PulpCommand]:
     return click.command(name=name, cls=PulpCommand, **kwargs)
 
 
-def pulp_group(name: Optional[str] = None, **kwargs: Any) -> Callable[[F], click.Group]:
+def pulp_group(
+    name: t.Optional[str] = None, **kwargs: t.Any
+) -> t.Callable[[_AnyCallable], PulpGroup]:
     return click.group(name=name, cls=PulpGroup, **kwargs)
 
 
 class PulpOption(click.Option):
     def __init__(
         self,
-        *args: Any,
-        needs_plugins: Optional[List[PluginRequirement]] = None,
-        allowed_with_contexts: Optional[Tuple[Type[PulpEntityContext]]] = None,
-        **kwargs: Any,
+        *args: t.Any,
+        needs_plugins: t.Optional[t.List[PluginRequirement]] = None,
+        allowed_with_contexts: t.Optional[t.Tuple[t.Type[PulpEntityContext]]] = None,
+        **kwargs: t.Any,
     ):
         self.needs_plugins = needs_plugins
         self.allowed_with_contexts = allowed_with_contexts
         super().__init__(*args, **kwargs)
 
-    def process_value(self, ctx: click.Context, value: Any) -> Any:
+    def process_value(self, ctx: click.Context, value: t.Any) -> t.Any:
         if self.needs_plugins and value is not None and value != ():
             pulp_ctx = ctx.find_object(PulpCLIContext)
             assert pulp_ctx is not None
@@ -272,7 +280,7 @@ def process_value(self, ctx: click.Context, value: Any) -> Any:
                 pulp_ctx.needs_plugin(plugin_requirement)
         return super().process_value(ctx, value)
 
-    def get_help_record(self, ctx: click.Context) -> Optional[Tuple[str, str]]:
+    def get_help_record(self, ctx: click.Context) -> t.Optional[t.Tuple[str, str]]:
         tmp = super().get_help_record(ctx)
         if tmp is None:
             return None
@@ -284,8 +292,8 @@ def get_help_record(self, ctx: click.Context) -> Optional[Tuple[str, str]]:
 
 
 class GroupOption(PulpOption):
-    def __init__(self, *args: Any, **kwargs: Any) -> None:
-        self.group: List[str] = kwargs.pop("group")
+    def __init__(self, *args: t.Any, **kwargs: t.Any) -> None:
+        self.group: t.List[str] = kwargs.pop("group")
         assert self.group, "'group' parameter required"
         kwargs["help"] = (
             kwargs.get("help", "")
@@ -295,8 +303,8 @@ def __init__(self, *args: Any, **kwargs: Any) -> None:
         super().__init__(*args, **kwargs)
 
     def handle_parse_result(
-        self, ctx: click.Context, opts: Mapping[str, Any], args: List[Any]
-    ) -> Any:
+        self, ctx: click.Context, opts: t.Mapping[str, t.Any], args: t.List[t.Any]
+    ) -> t.Any:
         assert self.name is not None
         all_options = self.group + [self.name]
         options_present = [x for x in all_options if x in opts]
@@ -322,11 +330,11 @@ def handle_parse_result(
 
 @lru_cache(typed=True)
 def lookup_callback(
-    attribute: str, context_class: Type[PulpEntityContext] = PulpEntityContext
-) -> Callable[[click.Context, click.Parameter, Optional[str]], Optional[str]]:
+    attribute: str, context_class: t.Type[PulpEntityContext] = PulpEntityContext
+) -> t.Callable[[click.Context, click.Parameter, t.Optional[str]], t.Optional[str]]:
     def _callback(
-        ctx: click.Context, param: click.Parameter, value: Optional[str]
-    ) -> Optional[str]:
+        ctx: click.Context, param: click.Parameter, value: t.Optional[str]
+    ) -> t.Optional[str]:
         if value is not None:
             if value == "":
                 value = "null"
@@ -339,11 +347,11 @@ def _callback(
 
 
 def href_callback(
-    context_class: Type[PulpEntityContext] = PulpEntityContext,
-) -> Callable[[click.Context, click.Parameter, Optional[str]], Optional[str]]:
+    context_class: t.Type[PulpEntityContext] = PulpEntityContext,
+) -> t.Callable[[click.Context, click.Parameter, t.Optional[str]], t.Optional[str]]:
     def _href_callback(
-        ctx: click.Context, param: click.Parameter, value: Optional[str]
-    ) -> Optional[str]:
+        ctx: click.Context, param: click.Parameter, value: t.Optional[str]
+    ) -> t.Optional[str]:
         if value is not None:
             entity_ctx = ctx.find_object(context_class)
             assert entity_ctx is not None
@@ -354,8 +362,8 @@ def _href_callback(
 
 
 def _version_callback(
-    ctx: click.Context, param: click.Parameter, value: Optional[int]
-) -> Optional[int]:
+    ctx: click.Context, param: click.Parameter, value: t.Optional[int]
+) -> t.Optional[int]:
     entity_ctx = ctx.find_object(PulpEntityContext)
     assert entity_ctx is not None
     repository_ctx = ctx.find_object(PulpRepositoryContext)
@@ -367,13 +375,13 @@ def _version_callback(
     return value
 
 
-def load_file_wrapper(handler: Callable[[click.Context, click.Parameter, str], Any]) -> Any:
+def load_file_wrapper(handler: t.Callable[[click.Context, click.Parameter, str], t.Any]) -> t.Any:
     """A wrapper that used for chaining or decorating callbacks that manipulate with input data."""
 
     @wraps(handler)
     def _load_file_or_string_wrapper(
-        ctx: click.Context, param: click.Parameter, value: Optional[str]
-    ) -> Any:
+        ctx: click.Context, param: click.Parameter, value: t.Optional[str]
+    ) -> t.Any:
         """Load the string from input, or from file if the value starts with @."""
         if not value:
             return value
@@ -398,7 +406,7 @@ def _load_file_or_string_wrapper(
 load_string_callback = load_file_wrapper(lambda c, p, x: x)
 
 
-def json_callback(ctx: click.Context, param: click.Parameter, value: Optional[str]) -> Any:
+def json_callback(ctx: click.Context, param: click.Parameter, value: t.Optional[str]) -> t.Any:
     if value is None:
         return None
 
@@ -414,8 +422,8 @@ def json_callback(ctx: click.Context, param: click.Parameter, value: Optional[st
 
 
 def load_labels_callback(
-    ctx: click.Context, param: click.Parameter, value: Optional[str]
-) -> Optional[Dict[str, str]]:
+    ctx: click.Context, param: click.Parameter, value: t.Optional[str]
+) -> t.Optional[t.Dict[str, str]]:
     if value is None:
         return value
 
@@ -428,12 +436,12 @@ def load_labels_callback(
 
 
 def create_content_json_callback(
-    context_class: Optional[Type[PulpContentContext]] = None, schema: s.Schema = None
-) -> Any:
+    context_class: t.Optional[t.Type[PulpContentContext]] = None, schema: s.Schema = None
+) -> t.Any:
     @load_file_wrapper
     def _callback(
         ctx: click.Context, param: click.Parameter, value: str
-    ) -> Optional[List[PulpContentContext]]:
+    ) -> t.Optional[t.List[PulpContentContext]]:
         ctx_class = context_class
         new_value = json_callback(ctx, param, value)
         if new_value is not None:
@@ -472,8 +480,8 @@ def parse_size_callback(ctx: click.Context, param: click.Parameter, value: str)
 
 
 def null_callback(
-    ctx: click.Context, param: click.Parameter, value: Optional[str]
-) -> Optional[str]:
+    ctx: click.Context, param: click.Parameter, value: t.Optional[str]
+) -> t.Optional[str]:
     if value == "":
         return "null"
     return value
@@ -483,7 +491,7 @@ def null_callback(
 # Decorator common options
 
 
-def pulp_option(*args: Any, **kwargs: Any) -> Callable[[FC], FC]:
+def pulp_option(*args: t.Any, **kwargs: t.Any) -> t.Callable[[FC], FC]:
     kwargs["cls"] = PulpOption
     return click.option(*args, **kwargs)
 
@@ -491,12 +499,12 @@ def pulp_option(*args: Any, **kwargs: Any) -> Callable[[FC], FC]:
 domain_pattern = r"(?P<pulp_domain>[-a-zA-Z0-9_]+)"
 
 
-def resource_lookup_option(*args: Any, **kwargs: Any) -> Callable[[FC], FC]:
+def resource_lookup_option(*args: t.Any, **kwargs: t.Any) -> t.Callable[[FC], FC]:
     lookup_key: str = kwargs.pop("lookup_key", "name")
-    context_class: Type[PulpEntityContext] = kwargs.pop("context_class")
+    context_class: t.Type[PulpEntityContext] = kwargs.pop("context_class")
 
     def _option_callback(
-        ctx: click.Context, param: click.Parameter, value: Optional[str]
+        ctx: click.Context, param: click.Parameter, value: t.Optional[str]
     ) -> EntityFieldDefinition:
         # Pass None and "" verbatim
         if not value:
@@ -542,26 +550,26 @@ def _option_callback(
     return click.option(*args, **kwargs)
 
 
-def resource_option(*args: Any, **kwargs: Any) -> Callable[[FC], FC]:
-    default_plugin: Optional[str] = kwargs.pop("default_plugin", None)
-    default_type: Optional[str] = kwargs.pop("default_type", None)
+def resource_option(*args: t.Any, **kwargs: t.Any) -> t.Callable[[FC], FC]:
+    default_plugin: t.Optional[str] = kwargs.pop("default_plugin", None)
+    default_type: t.Optional[str] = kwargs.pop("default_type", None)
     lookup_key: str = kwargs.pop("lookup_key", "name")
-    context_table: Dict[str, Type[PulpEntityContext]] = kwargs.pop("context_table")
-    capabilities: Optional[List[str]] = kwargs.pop("capabilities", None)
-    href_pattern: Optional[str] = kwargs.pop("href_pattern", None)
-    parent_resource_lookup: Optional[Tuple[str, Type[PulpEntityContext]]] = kwargs.pop(
+    context_table: t.Dict[str, t.Type[PulpEntityContext]] = kwargs.pop("context_table")
+    capabilities: t.Optional[t.List[str]] = kwargs.pop("capabilities", None)
+    href_pattern: t.Optional[str] = kwargs.pop("href_pattern", None)
+    parent_resource_lookup: t.Optional[t.Tuple[str, t.Type[PulpEntityContext]]] = kwargs.pop(
         "parent_resource_lookup", None
     )
 
     def _option_callback(
-        ctx: click.Context, param: click.Parameter, value: Optional[str]
+        ctx: click.Context, param: click.Parameter, value: t.Optional[str]
     ) -> EntityFieldDefinition:
         # Pass None and "" verbatim
         if not value:
             return value
 
-        pulp_href: Optional[str] = None
-        entity: Optional[EntityDefinition] = None
+        pulp_href: t.Optional[str] = None
+        entity: t.Optional[EntityDefinition] = None
 
         pulp_ctx = ctx.find_object(PulpCLIContext)
         assert pulp_ctx is not None
@@ -643,8 +651,8 @@ def _option_callback(
         return entity_ctx
 
     def _multi_option_callback(
-        ctx: click.Context, param: click.Parameter, value: Iterable[Optional[str]]
-    ) -> Iterable[EntityFieldDefinition]:
+        ctx: click.Context, param: click.Parameter, value: t.Iterable[t.Optional[str]]
+    ) -> t.Iterable[EntityFieldDefinition]:
         if value:
             return (_option_callback(ctx, param, item) for item in value)
         return tuple()
@@ -674,8 +682,8 @@ def _multi_option_callback(
     return click.option(*args, **kwargs)
 
 
-def type_option(*args: Any, **kwargs: Any) -> Callable[[FC], FC]:
-    choices: Dict[str, Type[PulpEntityContext]] = kwargs.pop("choices")
+def type_option(*args: t.Any, **kwargs: t.Any) -> t.Callable[[FC], FC]:
+    choices: t.Dict[str, t.Type[PulpEntityContext]] = kwargs.pop("choices")
     assert choices and isinstance(choices, dict)
     type_names = list(choices.keys())
     case_sensitive = kwargs.pop("case_sensitive", False)
@@ -686,7 +694,7 @@ def type_option(*args: Any, **kwargs: Any) -> Callable[[FC], FC]:
         "expose_value": False,
     }
 
-    def _type_callback(ctx: click.Context, param: click.Parameter, value: Optional[str]) -> str:
+    def _type_callback(ctx: click.Context, param: click.Parameter, value: t.Optional[str]) -> str:
         pulp_ctx = ctx.find_object(PulpCLIContext)
         assert pulp_ctx
         if value is not None:
@@ -1051,14 +1059,16 @@ def _type_callback(ctx: click.Context, param: click.Parameter, value: Optional[s
 # Generic reusable commands
 
 
-def list_command(**kwargs: Any) -> click.Command:
+def list_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a list command."""
 
     kwargs.setdefault("name", "list")
     kwargs.setdefault("help", _("Show the list of optionally filtered {entities}."))
     decorators = kwargs.pop("decorators", [])
 
-    @pulp_command(**kwargs)
+    # This is a mypy bug getting confused with positional args
+    # https://github.com/python/mypy/issues/15037
+    @pulp_command(**kwargs)  # type: ignore [arg-type]
     @limit_option
     @offset_option
     @ordering_option
@@ -1071,7 +1081,7 @@ def callback(
         entity_ctx: PulpEntityContext,
         limit: int,
         offset: int,
-        **kwargs: Any,
+        **kwargs: t.Any,
     ) -> None:
         """
         Show the list of optionally filtered {entities}.
@@ -1089,7 +1099,7 @@ def callback(
     return callback
 
 
-def show_command(**kwargs: Any) -> click.Command:
+def show_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a show command."""
 
     if "name" not in kwargs:
@@ -1113,7 +1123,7 @@ def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext) -> None:
     return callback
 
 
-def create_command(**kwargs: Any) -> click.Command:
+def create_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a create command."""
 
     if "name" not in kwargs:
@@ -1122,10 +1132,12 @@ def create_command(**kwargs: Any) -> click.Command:
         kwargs["help"] = _("Create a {entity}.")
     decorators = kwargs.pop("decorators", [])
 
-    @pulp_command(**kwargs)
+    # This is a mypy bug getting confused with positional args
+    # https://github.com/python/mypy/issues/15037
+    @pulp_command(**kwargs)  # type: ignore [arg-type]
     @pass_entity_context
     @pass_pulp_context
-    def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, **kwargs: Any) -> None:
+    def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, **kwargs: t.Any) -> None:
         """
         Create a {entity}.
         """
@@ -1141,7 +1153,7 @@ def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, **kwargs:
     return callback
 
 
-def update_command(**kwargs: Any) -> click.Command:
+def update_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates an update command."""
 
     if "name" not in kwargs:
@@ -1150,10 +1162,12 @@ def update_command(**kwargs: Any) -> click.Command:
         kwargs["help"] = _("Update a {entity}.")
     decorators = kwargs.pop("decorators", [])
 
-    @pulp_command(**kwargs)
+    # This is a mypy bug getting confused with positional args
+    # https://github.com/python/mypy/issues/15037
+    @pulp_command(**kwargs)  # type: ignore [arg-type]
     @pass_entity_context
     @pass_pulp_context
-    def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, **kwargs: Any) -> None:
+    def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, **kwargs: t.Any) -> None:
         """
         Update a {entity}.
         """
@@ -1165,7 +1179,7 @@ def callback(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, **kwargs:
     return callback
 
 
-def destroy_command(**kwargs: Any) -> click.Command:
+def destroy_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a destroy command."""
 
     kwargs.setdefault("name", "destroy")
@@ -1186,7 +1200,7 @@ def callback(entity_ctx: PulpEntityContext) -> None:
     return callback
 
 
-def version_command(**kwargs: Any) -> click.Command:
+def version_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a repository version command group."""
 
     kwargs.setdefault("name", "version")
@@ -1223,7 +1237,7 @@ def repair(
     return callback
 
 
-def label_command(**kwargs: Any) -> click.Command:
+def label_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a label command group."""
 
     kwargs.setdefault("name", "label")
@@ -1266,7 +1280,7 @@ def label_show(entity_ctx: PulpEntityContext, key: str) -> None:
     return label_group
 
 
-def role_command(**kwargs: Any) -> click.Command:
+def role_command(**kwargs: t.Any) -> click.Command:
     """A factory that creates a (object) role command group."""
 
     kwargs.setdefault("name", "role")
@@ -1301,8 +1315,8 @@ def role_add(
         pulp_ctx: PulpCLIContext,
         entity_ctx: PulpEntityContext,
         role: str,
-        users: List[str],
-        groups: List[str],
+        users: t.List[str],
+        groups: t.List[str],
     ) -> None:
         result = entity_ctx.add_role(role, users, groups)
         pulp_ctx.output_result(result)
@@ -1317,8 +1331,8 @@ def role_remove(
         pulp_ctx: PulpCLIContext,
         entity_ctx: PulpEntityContext,
         role: str,
-        users: List[str],
-        groups: List[str],
+        users: t.List[str],
+        groups: t.List[str],
     ) -> None:
         result = entity_ctx.remove_role(role, users, groups)
         pulp_ctx.output_result(result)
@@ -1331,13 +1345,13 @@ def role_remove(
     return role_group
 
 
-def repository_content_command(**kwargs: Any) -> click.Group:
+def repository_content_command(**kwargs: t.Any) -> click.Group:
     """A factory that creates a repository content command group."""
 
     content_contexts = kwargs.pop("contexts", {})
 
     def version_callback(
-        ctx: click.Context, param: click.Parameter, value: Optional[int]
+        ctx: click.Context, param: click.Parameter, value: t.Optional[int]
     ) -> PulpRepositoryVersionContext:
         repo_ctx = ctx.find_object(PulpRepositoryContext)
         assert repo_ctx is not None
@@ -1349,7 +1363,9 @@ def version_callback(
         )
         return repo_ver_ctx
 
-    @pulp_command("list")
+    # This is a mypy bug getting confused with positional args
+    # https://github.com/python/mypy/issues/15037
+    @pulp_command("list")  # type: ignore [arg-type]
     @click.option("--all-types", is_flag=True)
     @limit_option
     @offset_option
@@ -1364,7 +1380,7 @@ def content_list(
         offset: int,
         limit: int,
         all_types: bool,
-        **params: Any,
+        **params: t.Any,
     ) -> None:
         parameters = {k: v for k, v in params.items() if v is not None}
         parameters.update({"repository_version": version.pulp_href})
@@ -1402,15 +1418,15 @@ def content_remove(
     @click.option("--base-version", type=int, callback=version_callback)
     def content_modify(
         base_version: PulpRepositoryVersionContext,
-        add_content: Optional[List[PulpContentContext]],
-        remove_content: Optional[List[PulpContentContext]],
+        add_content: t.Optional[t.List[PulpContentContext]],
+        remove_content: t.Optional[t.List[PulpContentContext]],
     ) -> None:
         repo_ctx = base_version.repository_ctx
         ac = [unit.pulp_href for unit in add_content] if add_content else None
         rc = [unit.pulp_href for unit in remove_content] if remove_content else None
         repo_ctx.modify(add_content=ac, remove_content=rc, base_version=base_version.pulp_href)
 
-    command_decorators: Dict[click.Command, Optional[List[Callable[[FC], FC]]]] = {
+    command_decorators: t.Dict[click.Command, t.Optional[t.List[t.Callable[[FC], FC]]]] = {
         content_list: kwargs.pop("list_decorators", []),
         content_add: kwargs.pop("add_decorators", None),
         content_remove: kwargs.pop("remove_decorators", None),
diff --git a/pulpcore/cli/container/distribution.py b/pulpcore/cli/container/distribution.py
index 57770b21a..78aaae6e0 100644
--- a/pulpcore/cli/container/distribution.py
+++ b/pulpcore/cli/container/distribution.py
@@ -101,7 +101,7 @@ def distribution(ctx: click.Context, pulp_ctx: PulpCLIContext, distribution_type
 @pulp_labels_option
 @pass_entity_context
 def update(
-    distribution_ctx: PulpContainerDistributionContext,
+    distribution_ctx: PulpEntityContext,
     base_path: Optional[str],
     repository: Optional[Union[str, PulpEntityContext]],
     content_guard: EntityFieldDefinition,
@@ -109,6 +109,8 @@ def update(
     private: Optional[bool],
     pulp_labels: Optional[Dict[str, str]],
 ) -> None:
+    assert isinstance(distribution_ctx, PulpContainerDistributionContext)
+
     distribution: EntityDefinition = distribution_ctx.entity
     body: EntityDefinition = {}
 
diff --git a/pulpcore/cli/container/repository.py b/pulpcore/cli/container/repository.py
index 439bf9d13..40068e44f 100644
--- a/pulpcore/cli/container/repository.py
+++ b/pulpcore/cli/container/repository.py
@@ -182,10 +182,12 @@ def sync(
 @click.option("--digest", help=_("SHA256 digest of the Manifest file"), required=True)
 @pass_repository_context
 def add_tag(
-    repository_ctx: PulpContainerBaseRepositoryContext,
+    repository_ctx: PulpRepositoryContext,
     digest: str,
     tag: str,
 ) -> None:
+    assert isinstance(repository_ctx, PulpContainerBaseRepositoryContext)
+
     digest = digest.strip()
     if not digest.startswith("sha256:"):
         digest = f"sha256:{digest}"
@@ -201,7 +203,9 @@ def add_tag(
 @repository_lookup_option
 @click.option("--tag", help=_("Name of tag to remove"), required=True, callback=_tag_callback)
 @pass_repository_context
-def remove_tag(repository_ctx: PulpContainerBaseRepositoryContext, tag: str) -> None:
+def remove_tag(repository_ctx: PulpRepositoryContext, tag: str) -> None:
+    assert isinstance(repository_ctx, PulpContainerBaseRepositoryContext)
+
     repository_ctx.untag(tag)
 
 
@@ -219,11 +223,13 @@ def remove_tag(repository_ctx: PulpContainerBaseRepositoryContext, tag: str) ->
 )
 @pass_repository_context
 def copy_tag(
-    repository_ctx: PulpContainerRepositoryContext,
+    repository_ctx: PulpRepositoryContext,
     source: PulpRepositoryContext,
     version: Optional[int],
     tags: List[str],
 ) -> None:
+    assert isinstance(repository_ctx, PulpContainerRepositoryContext)
+
     href = source.entity["latest_version_href"]
     if version is not None:
         latest_version = int(href.split("/")[-2])
@@ -267,12 +273,14 @@ def copy_tag(
 )
 @pass_repository_context
 def copy_manifest(
-    repository_ctx: PulpContainerRepositoryContext,
+    repository_ctx: PulpRepositoryContext,
     source: PulpRepositoryContext,
     version: Optional[int],
     digests: List[str],
     media_types: List[str],
 ) -> None:
+    assert isinstance(repository_ctx, PulpContainerRepositoryContext)
+
     href = source.entity["latest_version_href"]
     if version is not None:
         latest_version = int(href.split("/")[-2])
@@ -297,9 +305,11 @@ def copy_manifest(
 @click.option("--digest", help=_("SHA256 digest of the Manifest file"), required=True)
 @pass_repository_context
 def remove_image(
-    repository_ctx: PulpContainerPushRepositoryContext,
+    repository_ctx: PulpRepositoryContext,
     digest: str,
 ) -> None:
+    assert isinstance(repository_ctx, PulpContainerPushRepositoryContext)
+
     digest = digest.strip()
     if not digest.startswith("sha256:"):
         digest = f"sha256:{digest}"
diff --git a/pulpcore/cli/core/access_policy.py b/pulpcore/cli/core/access_policy.py
index 852763211..a9b6ef9c5 100644
--- a/pulpcore/cli/core/access_policy.py
+++ b/pulpcore/cli/core/access_policy.py
@@ -1,4 +1,5 @@
 import click
+from pulp_glue.common.context import PulpEntityContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import PulpAccessPolicyContext
 
@@ -46,6 +47,8 @@ def access_policy(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @click.option("--viewset-name", callback=lookup_callback("viewset_name"), expose_value=False)
 @pass_entity_context
 @pass_pulp_context
-def reset(pulp_ctx: PulpCLIContext, access_policy_ctx: PulpAccessPolicyContext) -> None:
+def reset(pulp_ctx: PulpCLIContext, access_policy_ctx: PulpEntityContext) -> None:
+    assert isinstance(access_policy_ctx, PulpAccessPolicyContext)
+
     result = access_policy_ctx.reset()
     pulp_ctx.output_result(result)
diff --git a/pulpcore/cli/core/artifact.py b/pulpcore/cli/core/artifact.py
index 6ff4771f3..49c427ec0 100644
--- a/pulpcore/cli/core/artifact.py
+++ b/pulpcore/cli/core/artifact.py
@@ -1,6 +1,7 @@
 from typing import IO
 
 import click
+from pulp_glue.common.context import PulpEntityContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import PulpArtifactContext
 
@@ -66,9 +67,11 @@ def artifact(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @pass_pulp_context
 def upload(
     pulp_ctx: PulpCLIContext,
-    artifact_ctx: PulpArtifactContext,
+    artifact_ctx: PulpEntityContext,
     file: IO[bytes],
     chunk_size: int,
 ) -> None:
+    assert isinstance(artifact_ctx, PulpArtifactContext)
+
     artifact_ctx.upload(file, chunk_size)
     pulp_ctx.output_result(artifact_ctx.entity)
diff --git a/pulpcore/cli/core/content_guard.py b/pulpcore/cli/core/content_guard.py
index bb23954a8..cf1871d99 100644
--- a/pulpcore/cli/core/content_guard.py
+++ b/pulpcore/cli/core/content_guard.py
@@ -2,7 +2,7 @@
 
 import click
 from pulp_glue.certguard.context import PulpRHSMCertGuardContext, PulpX509CertGuardContext
-from pulp_glue.common.context import PulpContentGuardContext
+from pulp_glue.common.context import PulpContentGuardContext, PulpEntityContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import (
     PulpContentRedirectContentGuardContext,
@@ -77,10 +77,12 @@ def rbac(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @pass_pulp_context
 def assign(
     pulp_ctx: PulpCLIContext,
-    guard_ctx: PulpRbacContentGuardContext,
+    guard_ctx: PulpEntityContext,
     users: Optional[List[str]],
     groups: Optional[List[str]],
 ) -> None:
+    assert isinstance(guard_ctx, PulpRbacContentGuardContext)
+
     result = guard_ctx.assign(users=users, groups=groups)
     pulp_ctx.output_result(result)
 
@@ -104,10 +106,12 @@ def assign(
 @pass_pulp_context
 def remove(
     pulp_ctx: PulpCLIContext,
-    guard_ctx: PulpRbacContentGuardContext,
+    guard_ctx: PulpEntityContext,
     users: Optional[List[str]],
     groups: Optional[List[str]],
 ) -> None:
+    assert isinstance(guard_ctx, PulpRbacContentGuardContext)
+
     result = guard_ctx.remove(users=users, groups=groups)
     pulp_ctx.output_result(result)
 
diff --git a/pulpcore/cli/core/export.py b/pulpcore/cli/core/export.py
index e93357f8c..c147afecb 100644
--- a/pulpcore/cli/core/export.py
+++ b/pulpcore/cli/core/export.py
@@ -15,7 +15,6 @@
     PulpCLIContext,
     destroy_command,
     href_option,
-    pass_entity_context,
     pass_pulp_context,
     pulp_group,
     show_command,
@@ -24,6 +23,8 @@
 translation = get_translation(__name__)
 _ = translation.gettext
 
+pass_export_context = click.make_pass_decorator(PulpExportContext)
+
 
 def _version_list_callback(
     ctx: click.Context, param: click.Parameter, value: Iterable[Tuple[str, int]]
@@ -98,13 +99,15 @@ def pulp(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 pulp.add_command(destroy_command(decorators=lookup_options))
 
 
-@pulp.command()
+# This is a mypy bug getting confused with positional args
+# https://github.com/python/mypy/issues/15037
+@pulp.command()  # type: ignore [arg-type]
 @click.option("--exporter", type=str, required=True, help=_("Name of owning PulpExporter"))
 @click.option(
     "--limit", default=DEFAULT_LIMIT, type=int, help=_("Limit the number of exporters to show.")
 )
 @click.option("--offset", default=0, type=int, help=_("Skip a number of exporters to show."))
-@pass_entity_context
+@pass_export_context
 @pass_pulp_context
 def list(
     pulp_ctx: PulpCLIContext,
@@ -129,7 +132,7 @@ def list(
 @click.option(
     "--start-versions", type=tuple([str, int]), multiple=True, callback=_version_list_callback
 )
-@pass_entity_context
+@pass_export_context
 @pass_pulp_context
 def run(
     pulp_ctx: PulpCLIContext,
diff --git a/pulpcore/cli/core/exporter.py b/pulpcore/cli/core/exporter.py
index 548d88223..38fb44ffb 100644
--- a/pulpcore/cli/core/exporter.py
+++ b/pulpcore/cli/core/exporter.py
@@ -1,7 +1,7 @@
 from typing import Any, Dict, Iterable
 
 import click
-from pulp_glue.common.context import EntityFieldDefinition, PulpEntityContext, PulpRepositoryContext
+from pulp_glue.common.context import EntityFieldDefinition, PulpRepositoryContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import PulpExporterContext
 
@@ -11,7 +11,6 @@
     href_option,
     list_command,
     name_option,
-    pass_entity_context,
     pass_pulp_context,
     pulp_group,
     resource_option,
@@ -21,6 +20,8 @@
 translation = get_translation(__name__)
 _ = translation.gettext
 
+pass_exporter_context = click.make_pass_decorator(PulpExporterContext)
+
 
 multi_repository_option = resource_option(
     "--repository",
@@ -60,7 +61,7 @@ def pulp(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @click.option("--path", required=True)
 @multi_repository_option
 @click.option("--repository-href", multiple=True)
-@pass_entity_context
+@pass_exporter_context
 @pass_pulp_context
 def create(
     pulp_ctx: PulpCLIContext,
@@ -73,7 +74,7 @@ def create(
     repo_hrefs = [
         repository_ctx.pulp_href
         for repository_ctx in repository
-        if isinstance(repository_ctx, PulpEntityContext)
+        if isinstance(repository_ctx, PulpRepositoryContext)
     ] + list(repository_href)
 
     params = {"name": name, "path": path, "repositories": repo_hrefs}
@@ -87,7 +88,7 @@ def create(
 @click.option("--path")
 @multi_repository_option
 @click.option("--repository-href", multiple=True)  # This should be deprecated
-@pass_entity_context
+@pass_exporter_context
 @pass_pulp_context
 def update(
     pulp_ctx: PulpCLIContext,
@@ -105,7 +106,7 @@ def update(
         payload["repositories"] = [
             repository_ctx.pulp_href
             for repository_ctx in repository
-            if isinstance(repository_ctx, PulpEntityContext)
+            if isinstance(repository_ctx, PulpRepositoryContext)
         ] + list(repository_href)
 
     exporter_ctx.update(body=payload)
diff --git a/pulpcore/cli/core/group.py b/pulpcore/cli/core/group.py
index fc356c322..cd42fc363 100644
--- a/pulpcore/cli/core/group.py
+++ b/pulpcore/cli/core/group.py
@@ -1,7 +1,7 @@
 from typing import Optional
 
 import click
-from pulp_glue.common.context import PluginRequirement
+from pulp_glue.common.context import PluginRequirement, PulpEntityContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import (
     PulpDomainContext,
@@ -34,6 +34,8 @@
 translation = get_translation(__name__)
 _ = translation.gettext
 
+pass_group_context = click.make_pass_decorator(PulpGroupContext)
+
 
 def _object_callback(ctx: click.Context, param: click.Parameter, value: str) -> str:
     entity_ctx = ctx.find_object(PulpGroupPermissionContext)
@@ -117,7 +119,7 @@ def group(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
     type=click.Choice(["model", "object"], case_sensitive=False),
     default="model",
 )
-@pass_entity_context
+@pass_group_context
 @pass_pulp_context
 @click.pass_context
 def permission(
@@ -146,9 +148,9 @@ def permission(
 @click.option("--permission", required=True)
 @click.option("--object", "obj", callback=_object_callback)
 @pass_entity_context
-def add_permission(
-    entity_ctx: PulpGroupPermissionContext, permission: str, obj: Optional[str]
-) -> None:
+def add_permission(entity_ctx: PulpEntityContext, permission: str, obj: Optional[str]) -> None:
+    assert isinstance(entity_ctx, PulpGroupPermissionContext)
+
     body = {"permission": permission}
     if obj:
         body["obj"] = obj
@@ -174,7 +176,7 @@ def add_permission(
 
 
 @group.group()
-@pass_entity_context
+@pass_group_context
 @pass_pulp_context
 @click.pass_context
 def user(ctx: click.Context, pulp_ctx: PulpCLIContext, group_ctx: PulpGroupContext) -> None:
@@ -193,7 +195,9 @@ def user(ctx: click.Context, pulp_ctx: PulpCLIContext, group_ctx: PulpGroupConte
 @click.option("--username", required=True)
 @pass_entity_context
 @pass_pulp_context
-def remove_user(pulp_ctx: PulpCLIContext, entity_ctx: PulpGroupUserContext, username: str) -> None:
+def remove_user(pulp_ctx: PulpCLIContext, entity_ctx: PulpEntityContext, username: str) -> None:
+    assert isinstance(entity_ctx, PulpGroupUserContext)
+
     user_href = PulpUserContext(pulp_ctx).find(username=username)["pulp_href"]
     user_pk = user_href.split("/")[-2]
     group_user_href = f"{entity_ctx.group_ctx.pulp_href}users/{user_pk}/"
@@ -202,7 +206,7 @@ def remove_user(pulp_ctx: PulpCLIContext, entity_ctx: PulpGroupUserContext, user
 
 
 @group.group(name="role-assignment")
-@pass_entity_context
+@pass_group_context
 @pass_pulp_context
 @click.pass_context
 def role(ctx: click.Context, pulp_ctx: PulpCLIContext, group_ctx: PulpGroupContext) -> None:
diff --git a/pulpcore/cli/core/importer.py b/pulpcore/cli/core/importer.py
index c89932029..988a81c72 100644
--- a/pulpcore/cli/core/importer.py
+++ b/pulpcore/cli/core/importer.py
@@ -10,7 +10,6 @@
     href_option,
     list_command,
     name_option,
-    pass_entity_context,
     pass_pulp_context,
     pulp_group,
     show_command,
@@ -19,6 +18,9 @@
 translation = get_translation(__name__)
 _ = translation.gettext
 
+pass_importer_context = click.make_pass_decorator(PulpImporterContext)
+
+
 RepositoryMap = Tuple[str, str]  # source repo, destination repo
 
 repo_map_option = click.option(
@@ -54,7 +56,7 @@ def pulp(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @pulp.command()
 @click.option("--name", required=True)
 @repo_map_option
-@pass_entity_context
+@pass_importer_context
 @pass_pulp_context
 def create(
     pulp_ctx: PulpCLIContext,
@@ -75,7 +77,7 @@ def create(
 @name_option
 @href_option
 @repo_map_option
-@pass_entity_context
+@pass_importer_context
 @pass_pulp_context
 def update(
     pulp_ctx: PulpCLIContext,
diff --git a/pulpcore/cli/core/orphan.py b/pulpcore/cli/core/orphan.py
index 28498c01d..98c2a00bb 100644
--- a/pulpcore/cli/core/orphan.py
+++ b/pulpcore/cli/core/orphan.py
@@ -1,7 +1,7 @@
 from typing import Any
 
 import click
-from pulp_glue.common.context import PluginRequirement
+from pulp_glue.common.context import PluginRequirement, PulpEntityContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import PulpOrphanContext
 
@@ -28,7 +28,9 @@ def orphan(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
     ctx.obj = PulpOrphanContext(pulp_ctx)
 
 
-@orphan.command()
+# This is a mypy bug getting confused with positional args
+# https://github.com/python/mypy/issues/15037
+@orphan.command()  # type: ignore [arg-type]
 @pulp_option(
     "--content-hrefs",
     help=_("List of specific Contents to delete if they are orphans"),
@@ -47,8 +49,10 @@ def orphan(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 )
 @pass_entity_context
 @pass_pulp_context
-def cleanup(pulp_ctx: PulpCLIContext, orphan_ctx: PulpOrphanContext, **kwargs: Any) -> None:
+def cleanup(pulp_ctx: PulpCLIContext, orphan_ctx: PulpEntityContext, **kwargs: Any) -> None:
     """
     Cleanup orphaned content.
     """
+    assert isinstance(orphan_ctx, PulpOrphanContext)
+
     pulp_ctx.output_result(orphan_ctx.cleanup(kwargs))
diff --git a/pulpcore/cli/core/task.py b/pulpcore/cli/core/task.py
index 131465981..59c7a530f 100644
--- a/pulpcore/cli/core/task.py
+++ b/pulpcore/cli/core/task.py
@@ -17,7 +17,6 @@
     destroy_command,
     href_option,
     list_command,
-    pass_entity_context,
     pass_pulp_context,
     pulp_group,
     pulp_option,
@@ -29,6 +28,9 @@
 _ = translation.gettext
 
 
+pass_task_context = click.make_pass_decorator(PulpTaskContext)
+
+
 def _uuid_callback(
     ctx: click.Context, param: click.Parameter, value: Optional[str]
 ) -> Optional[str]:
@@ -113,7 +115,7 @@ def task(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @href_option
 @uuid_option
 @click.option("-w", "--wait", is_flag=True, help=_("Wait for the task to finish"))
-@pass_entity_context
+@pass_task_context
 @pass_pulp_context
 def show(pulp_ctx: PulpCLIContext, task_ctx: PulpTaskContext, wait: bool) -> None:
     """Shows details of a task."""
@@ -134,7 +136,7 @@ def show(pulp_ctx: PulpCLIContext, task_ctx: PulpTaskContext, wait: bool) -> Non
 )
 @click.option("--waiting", "waiting_tasks", is_flag=True, help=_("Cancel all 'waiting' tasks."))
 @click.option("--running", "running_tasks", is_flag=True, help=_("Cancel all 'running' tasks."))
-@pass_entity_context
+@pass_task_context
 @pass_pulp_context
 def cancel(
     pulp_ctx: PulpCLIContext,
@@ -181,7 +183,7 @@ def cancel(
     type=click.Choice(["skipped", "completed", "failed", "canceled"]),
     multiple=True,
 )
-@pass_entity_context
+@pass_task_context
 def purge(
     task_ctx: PulpTaskContext,
     finished: Optional[datetime],
@@ -192,7 +194,7 @@ def purge(
 
 
 @task.command()
-@pass_entity_context
+@pass_task_context
 @pass_pulp_context
 def summary(pulp_ctx: PulpCLIContext, task_ctx: PulpTaskContext) -> None:
     """
diff --git a/pulpcore/cli/core/task_group.py b/pulpcore/cli/core/task_group.py
index 36eac2313..91c7315e5 100644
--- a/pulpcore/cli/core/task_group.py
+++ b/pulpcore/cli/core/task_group.py
@@ -53,8 +53,10 @@ def _uuid_callback(
 @click.option("-w", "--wait", is_flag=True, help=_("Wait for the group-task to finish"))
 @pass_entity_context
 @pass_pulp_context
-def show(pulp_ctx: PulpCLIContext, task_group_ctx: PulpTaskGroupContext, wait: bool) -> None:
+def show(pulp_ctx: PulpCLIContext, task_group_ctx: PulpEntityContext, wait: bool) -> None:
     """Shows details of a group-task."""
+    assert isinstance(task_group_ctx, PulpTaskGroupContext)
+
     entity = task_group_ctx.entity
     if wait:
         if not entity["all_tasks_dispatched"]:
diff --git a/pulpcore/cli/core/user.py b/pulpcore/cli/core/user.py
index 1475d450c..d69ef46c5 100644
--- a/pulpcore/cli/core/user.py
+++ b/pulpcore/cli/core/user.py
@@ -1,7 +1,7 @@
 from typing import Optional
 
 import click
-from pulp_glue.common.context import PluginRequirement
+from pulp_glue.common.context import PluginRequirement, PulpEntityContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.core.context import PulpDomainContext, PulpUserContext, PulpUserRoleContext
 
@@ -111,7 +111,9 @@ def user(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 @pass_entity_context
 @pass_pulp_context
 @click.pass_context
-def role(ctx: click.Context, pulp_ctx: PulpCLIContext, user_ctx: PulpUserContext) -> None:
+def role(ctx: click.Context, pulp_ctx: PulpCLIContext, user_ctx: PulpEntityContext) -> None:
+    assert isinstance(user_ctx, PulpUserContext)
+
     pulp_ctx.needs_plugin(req_core_3_17)
     ctx.obj = PulpUserRoleContext(pulp_ctx, user_ctx)
 
diff --git a/pulpcore/cli/file/acs.py b/pulpcore/cli/file/acs.py
index 71bcd5156..56b9ab622 100644
--- a/pulpcore/cli/file/acs.py
+++ b/pulpcore/cli/file/acs.py
@@ -1,7 +1,7 @@
 from typing import Iterable
 
 import click
-from pulp_glue.common.context import PulpRemoteContext
+from pulp_glue.common.context import PulpACSContext, PulpRemoteContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.file.context import PulpFileACSContext, PulpFileRemoteContext
 
@@ -13,7 +13,7 @@
     href_option,
     list_command,
     name_option,
-    pass_entity_context,
+    pass_acs_context,
     pass_pulp_context,
     pulp_group,
     resource_option,
@@ -59,8 +59,8 @@ def path() -> None:
 @href_option
 @acs_lookup_option
 @path_option
-@pass_entity_context
-def add(acs_ctx: PulpFileACSContext, paths: Iterable[str]) -> None:
+@pass_acs_context
+def add(acs_ctx: PulpACSContext, paths: Iterable[str]) -> None:
     """Add path(s) to an existing ACS."""
     paths = set(paths)
     existing_paths = set(acs_ctx.entity["paths"])
@@ -79,8 +79,8 @@ def add(acs_ctx: PulpFileACSContext, paths: Iterable[str]) -> None:
 @href_option
 @acs_lookup_option
 @path_option
-@pass_entity_context
-def remove(acs_ctx: PulpFileACSContext, paths: Iterable[str]) -> None:
+@pass_acs_context
+def remove(acs_ctx: PulpACSContext, paths: Iterable[str]) -> None:
     """Remove path(s) from an existing ACS."""
     paths = set(paths)
     existing_paths = set(acs_ctx.entity["paths"])
@@ -114,10 +114,10 @@ def remove(acs_ctx: PulpFileACSContext, paths: Iterable[str]) -> None:
 
 
 @acs.command()
-@pass_entity_context
-@pass_pulp_context
+@acs_lookup_option
 @href_option
 @name_option
-@acs_lookup_option
-def refresh(pulp_ctx: PulpCLIContext, acs_ctx: PulpFileACSContext) -> None:
+@pass_acs_context
+@pass_pulp_context
+def refresh(pulp_ctx: PulpCLIContext, acs_ctx: PulpACSContext) -> None:
     acs_ctx.refresh()
diff --git a/pulpcore/cli/file/content.py b/pulpcore/cli/file/content.py
index 26f35272e..1ba7d6b6d 100644
--- a/pulpcore/cli/file/content.py
+++ b/pulpcore/cli/file/content.py
@@ -120,13 +120,15 @@ def content(ctx: click.Context, pulp_ctx: PulpCLIContext, content_type: str) ->
 @pass_pulp_context
 def upload(
     pulp_ctx: PulpCLIContext,
-    entity_ctx: PulpFileContentContext,
+    entity_ctx: PulpEntityContext,
     relative_path: str,
     file: IO[bytes],
     chunk_size: int,
     repository: Optional[PulpRepositoryContext],
 ) -> None:
     """Create a file content unit by uploading a file"""
+    assert isinstance(entity_ctx, PulpFileContentContext)
+
     result = entity_ctx.upload(
         relative_path=relative_path, file=file, chunk_size=chunk_size, repository=repository
     )
diff --git a/pulpcore/cli/migration/plan.py b/pulpcore/cli/migration/plan.py
index 223c831a2..1bd9f6346 100644
--- a/pulpcore/cli/migration/plan.py
+++ b/pulpcore/cli/migration/plan.py
@@ -8,7 +8,6 @@
     href_option,
     list_command,
     load_json_callback,
-    pass_entity_context,
     pass_pulp_context,
     pulp_group,
     show_command,
@@ -18,6 +17,8 @@
 translation = get_translation(__name__)
 _ = translation.gettext
 
+pass_migration_plan_context = click.make_pass_decorator(PulpMigrationPlanContext)
+
 
 @pulp_group()
 @pass_pulp_context
@@ -46,13 +47,13 @@ def plan(ctx: click.Context, pulp_ctx: PulpCLIContext) -> None:
 
 @plan.command(help=_("Run migration plan"))
 @click.option("--href", required=True, help=_("HREF of the plan"))
-@pass_entity_context
+@pass_migration_plan_context
 def run(plan_ctx: PulpMigrationPlanContext, href: str) -> None:
     plan_ctx.run(href)
 
 
 @plan.command(help=_("Reset Pulp 3 data for plugins specified in the migration plan"))
 @click.option("--href", required=True, help=_("HREF of the plan"))
-@pass_entity_context
+@pass_migration_plan_context
 def reset(plan_ctx: PulpMigrationPlanContext, href: str) -> None:
     plan_ctx.reset(href)
diff --git a/pulpcore/cli/python/content.py b/pulpcore/cli/python/content.py
index b6b128328..cb0d45384 100644
--- a/pulpcore/cli/python/content.py
+++ b/pulpcore/cli/python/content.py
@@ -96,13 +96,15 @@ def content(ctx: click.Context, pulp_ctx: PulpCLIContext, content_type: str) ->
 @pass_pulp_context
 def upload(
     pulp_ctx: PulpCLIContext,
-    entity_ctx: PulpPythonContentContext,
+    entity_ctx: PulpEntityContext,
     relative_path: str,
     file: IO[bytes],
     chunk_size: int,
     repository: Optional[PulpPythonRepositoryContext],
 ) -> None:
     """Create a Python package content unit through uploading a file"""
+    assert isinstance(entity_ctx, PulpPythonContentContext)
+
     result = entity_ctx.upload(
         relative_path=relative_path, file=file, chunk_size=chunk_size, repository=repository
     )
diff --git a/pulpcore/cli/rpm/acs.py b/pulpcore/cli/rpm/acs.py
index 07dabc56f..317185628 100644
--- a/pulpcore/cli/rpm/acs.py
+++ b/pulpcore/cli/rpm/acs.py
@@ -1,7 +1,7 @@
 from typing import Iterable
 
 import click
-from pulp_glue.common.context import PulpRemoteContext
+from pulp_glue.common.context import PulpACSContext, PulpRemoteContext
 from pulp_glue.common.i18n import get_translation
 from pulp_glue.rpm.context import PulpRpmACSContext, PulpRpmRemoteContext, PulpUlnRemoteContext
 
@@ -13,7 +13,7 @@
     href_option,
     list_command,
     name_option,
-    pass_entity_context,
+    pass_acs_context,
     pass_pulp_context,
     pulp_group,
     resource_option,
@@ -59,8 +59,8 @@ def path() -> None:
 @href_option
 @acs_lookup_option
 @path_option
-@pass_entity_context
-def add(acs_ctx: PulpRpmACSContext, paths: Iterable[str]) -> None:
+@pass_acs_context
+def add(acs_ctx: PulpACSContext, paths: Iterable[str]) -> None:
     """Add path(s) to an existing ACS."""
     paths = set(paths)
     existing_paths = set(acs_ctx.entity["paths"])
@@ -79,8 +79,8 @@ def add(acs_ctx: PulpRpmACSContext, paths: Iterable[str]) -> None:
 @href_option
 @acs_lookup_option
 @path_option
-@pass_entity_context
-def remove(acs_ctx: PulpRpmACSContext, paths: Iterable[str]) -> None:
+@pass_acs_context
+def remove(acs_ctx: PulpACSContext, paths: Iterable[str]) -> None:
     """Remove path(s) from an existing ACS."""
     paths = set(paths)
     existing_paths = set(acs_ctx.entity["paths"])
@@ -114,10 +114,10 @@ def remove(acs_ctx: PulpRpmACSContext, paths: Iterable[str]) -> None:
 
 
 @acs.command()
-@pass_entity_context
-@pass_pulp_context
-@href_option
 @acs_lookup_option
+@href_option
 @name_option
-def refresh(pulp_ctx: PulpCLIContext, acs_ctx: PulpRpmACSContext) -> None:
+@pass_acs_context
+@pass_pulp_context
+def refresh(pulp_ctx: PulpCLIContext, acs_ctx: PulpACSContext) -> None:
     acs_ctx.refresh()
diff --git a/pulpcore/cli/rpm/content.py b/pulpcore/cli/rpm/content.py
index 447b97ec6..758ef061c 100644
--- a/pulpcore/cli/rpm/content.py
+++ b/pulpcore/cli/rpm/content.py
@@ -247,7 +247,9 @@ def content() -> None:
 # upload takes a file-argument and creates the entity from it.
 # upload currently only works for advisory/package,
 # see https://github.com/pulp/pulp_rpm/issues/2534
-@content.command(
+# This is a mypy bug getting confused with positional args
+# https://github.com/python/mypy/issues/15037
+@content.command(  # type: ignore [arg-type]
     allowed_with_contexts=(
         PulpRpmPackageContext,
         PulpRpmAdvisoryContext,
@@ -278,10 +280,7 @@ def content() -> None:
 @pass_pulp_context
 def upload(
     pulp_ctx: PulpCLIContext,
-    entity_ctx: Union[
-        PulpRpmPackageContext,
-        PulpRpmAdvisoryContext,
-    ],
+    entity_ctx: PulpEntityContext,
     file: IO[bytes],
     chunk_size: int,
     **kwargs: Any,
diff --git a/setup.py b/setup.py
index ed59443ac..82b70d796 100644
--- a/setup.py
+++ b/setup.py
@@ -38,7 +38,7 @@
     python_requires=">=3.6",
     install_requires=[
         "pulp-glue==0.21.0.dev",
-        "click>=8.0.0,<8.1.4",
+        "click>=8.0.0,<8.1.7",
         "PyYAML>=5.3,<6.1",
         "schema>=0.7.5,<0.8",
         "toml>=0.10.2,<0.11",