diff --git a/.fides/systems.yml b/.fides/systems.yml
index e5d36896f2..429873ca8f 100644
--- a/.fides/systems.yml
+++ b/.fides/systems.yml
@@ -28,7 +28,7 @@ system:
           - fides_db
 
   # System Info
-  - fides_key: privacy_request_fullfillment
+  - fides_key: privacy_request_fulfillment
     name: Fides Privacy Request Fulfillment
     organization_fides_key: default_organization
     description: Privacy request fufillment.
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 56cfd6c1c5..8d66dfed1c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -44,6 +44,7 @@ The types of changes are:
 * Add warning to 'fides deploy' when installed outside of a virtual environment [#2641](https://github.com/ethyca/fides/pull/2641)
 * Redesigned the default/init config file to be auto-documented. Also updates the `fides init` logic and analytics consent logic [#2694](https://github.com/ethyca/fides/pull/2694)
 * Change how config creation/import is handled across the application [#2622](https://github.com/ethyca/fides/pull/2622)
+* Update the CLI aesthetics & docstrings [#2703](https://github.com/ethyca/fides/pull/2703)
 * Updates Roles->Scopes Mapping [#2744](https://github.com/ethyca/fides/pull/2744)
 * Return user scopes as an enum, as well as total scopes [#2741](https://github.com/ethyca/fides/pull/2741)
 
diff --git a/requirements.txt b/requirements.txt
index d4be59d3b8..ad520d2842 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -3,7 +3,6 @@ APScheduler==3.9.1.post1
 asyncpg==0.25.0
 boto3==1.26.1
 celery[pytest]==5.2.7
-click==8.1.3
 colorama>=0.4.3
 cryptography==38.0.3
 dask==2022.9.2
@@ -35,6 +34,7 @@ PyMySQL==1.0.2
 python-jose[cryptography]==3.3.0
 pyyaml>=5,<6
 redis==3.5.3
+rich-click==1.6.1
 sendgrid==6.9.7
 slowapi==0.1.5
 snowflake-sqlalchemy==1.4.3
diff --git a/src/fides/cli/__init__.py b/src/fides/cli/__init__.py
index efe8d2714f..fe02a594fc 100644
--- a/src/fides/cli/__init__.py
+++ b/src/fides/cli/__init__.py
@@ -1,14 +1,17 @@
-"""Contains the groups and setup for the CLI."""
+"""
+Entrypoint for the Fides command-line.
+"""
 from importlib.metadata import version
 from platform import system
 
-import click
+import rich_click as click
 from fideslog.sdk.python.client import AnalyticsClient
 
 import fides
 from fides.cli.utils import check_server
 from fides.core.config import get_config
 
+from . import cli_formatting
 from .commands.annotate import annotate
 from .commands.core import evaluate, parse, pull, push
 from .commands.crud import delete, get_resource, list_resources
@@ -58,24 +61,28 @@
     "--config-path",
     "-f",
     "config_path",
-    default="",
-    help="Path to a configuration file. Use 'fides view-config' to print the config. Not compatible with the 'fides webserver' subcommand.",
+    show_default=True,
+    help="Path to a Fides config file. _Defaults to `.fides/fides.toml`._",
 )
 @click.option(
     "--local",
     is_flag=True,
-    help="Run in 'local_mode'. This mode doesn't make API calls and can be used without the API server/database.",
+    help="Run in `local_mode`. This mode doesn't make API calls and can be used without the API server/database.",
 )
 @click.pass_context
 def cli(ctx: click.Context, config_path: str, local: bool) -> None:
     """
-    The parent group for the Fides CLI.
+    __Command-line tool for the Fides privacy engineering platform.__
+
+    ---
+
+    _Note: The common MANIFESTS_DIR argument _always_ defaults to ".fides/" if not specified._
     """
 
     ctx.ensure_object(dict)
     config = get_config(config_path, verbose=True)
 
-    # Dyanmically add commands to the CLI
+    # Dynamically add commands to the CLI
     cli.commands = LOCAL_COMMAND_DICT
 
     if not (local or config.cli.local_mode):
diff --git a/src/fides/cli/cli_formatting.py b/src/fides/cli/cli_formatting.py
new file mode 100644
index 0000000000..1da85f45f2
--- /dev/null
+++ b/src/fides/cli/cli_formatting.py
@@ -0,0 +1,114 @@
+"""
+This is a configuration file for `rich_click`, used to customize the
+visual aesthetic and output of the CLI.
+
+This is the list of all documented configuration options for `rich_click`.
+
+You can set a style attribute by adding one or more of the following words:
+
+- "bold" or "b" for bold text.
+- "blink" for text that flashes (use this one sparingly).
+- "blink2" for text that flashes rapidly (not supported by most terminals).
+- "conceal" for concealed text (not supported by most terminals).
+- "italic" or "i" for italic text (not supported on Windows).
+- "reverse" or "r" for text with foreground and background colors reversed.
+- "strike" or "s" for text with a line through it.
+- "underline" or "u" for underlined text.
+- "underline2" or "uu" for doubly underlined text.
+- "frame" for framed text.
+- "encircle" for encircled text.
+- "overline" or "o" for overlined text.
+
+The list of valid colors is here:
+- https://rich.readthedocs.io/en/stable/appendix/colors.html
+"""
+
+from rich_click import rich_click
+
+# Default styles
+rich_click.STYLE_OPTION = "bold #fca311"
+rich_click.STYLE_SWITCH = "bold #fca311"
+rich_click.STYLE_ARGUMENT = "bold #00ff5f"
+rich_click.STYLE_METAVAR = "bold #8700af"
+rich_click.STYLE_METAVAR_APPEND = "dim yellow"
+rich_click.STYLE_METAVAR_SEPARATOR = "dim"
+rich_click.STYLE_HEADER_TEXT = ""
+rich_click.STYLE_FOOTER_TEXT = ""
+rich_click.STYLE_USAGE = "yellow"
+rich_click.STYLE_USAGE_COMMAND = "bold"
+rich_click.STYLE_DEPRECATED = "red"
+rich_click.STYLE_HELPTEXT_FIRST_LINE = ""
+rich_click.STYLE_HELPTEXT = ""
+rich_click.STYLE_OPTION_HELP = ""
+rich_click.STYLE_OPTION_DEFAULT = "bold #8700af"
+rich_click.STYLE_OPTION_ENVVAR = "dim yellow"
+rich_click.STYLE_REQUIRED_SHORT = "red"
+rich_click.STYLE_REQUIRED_LONG = "dim red"
+rich_click.STYLE_OPTIONS_PANEL_BORDER = "dim"
+rich_click.ALIGN_OPTIONS_PANEL = "left"
+rich_click.STYLE_OPTIONS_TABLE_SHOW_LINES = False
+rich_click.STYLE_OPTIONS_TABLE_LEADING = 0
+rich_click.STYLE_OPTIONS_TABLE_PAD_EDGE = False
+rich_click.STYLE_OPTIONS_TABLE_PADDING = (0, 1)
+rich_click.STYLE_OPTIONS_TABLE_BOX = ""
+rich_click.STYLE_OPTIONS_TABLE_ROW_STYLES = None
+rich_click.STYLE_OPTIONS_TABLE_BORDER_STYLE = None
+rich_click.STYLE_COMMANDS_PANEL_BORDER = "dim"
+rich_click.ALIGN_COMMANDS_PANEL = "left"
+rich_click.STYLE_COMMANDS_TABLE_SHOW_LINES = False
+rich_click.STYLE_COMMANDS_TABLE_LEADING = 0
+rich_click.STYLE_COMMANDS_TABLE_PAD_EDGE = False
+rich_click.STYLE_COMMANDS_TABLE_PADDING = (0, 1)
+rich_click.STYLE_COMMANDS_TABLE_BOX = ""
+rich_click.STYLE_COMMANDS_TABLE_ROW_STYLES = None
+rich_click.STYLE_COMMANDS_TABLE_BORDER_STYLE = None
+rich_click.STYLE_ERRORS_PANEL_BORDER = "red"
+rich_click.ALIGN_ERRORS_PANEL = "left"
+rich_click.STYLE_ERRORS_SUGGESTION = "dim"
+rich_click.STYLE_ABORTED = "red"
+rich_click.MAX_WIDTH = None  # Set to an int to limit to that many characters
+rich_click.COLOR_SYSTEM = "auto"  # Set to None to disable colors
+
+# Fixed strings
+rich_click.HEADER_TEXT = None
+rich_click.FOOTER_TEXT = None
+rich_click.DEPRECATED_STRING = "(Deprecated) "
+rich_click.DEFAULT_STRING = "[default: {}]"
+rich_click.ENVVAR_STRING = "[env var: {}]"
+rich_click.REQUIRED_SHORT_STRING = "*"
+rich_click.REQUIRED_LONG_STRING = "[required]"
+rich_click.RANGE_STRING = " [{}]"
+rich_click.APPEND_METAVARS_HELP_STRING = "({})"
+rich_click.ARGUMENTS_PANEL_TITLE = "Arguments"
+rich_click.OPTIONS_PANEL_TITLE = "Options"
+rich_click.COMMANDS_PANEL_TITLE = "Commands"
+rich_click.ERRORS_PANEL_TITLE = "Error"
+rich_click.ERRORS_SUGGESTION = (
+    None  # Default: Try 'cmd -h' for help. Set to False to disable.
+)
+rich_click.ERRORS_EPILOGUE = None
+rich_click.ABORTED_TEXT = "Aborted."
+
+# Behaviours
+rich_click.SHOW_ARGUMENTS = True  # Show positional arguments
+rich_click.SHOW_METAVARS_COLUMN = (
+    True  # Show a column with the option metavar (eg. INTEGER)
+)
+rich_click.APPEND_METAVARS_HELP = (
+    False  # Append metavar (eg. [TEXT]) after the help text
+)
+rich_click.GROUP_ARGUMENTS_OPTIONS = (
+    False  # Show arguments with options instead of in own panel
+)
+rich_click.USE_MARKDOWN = True  # Parse help strings as markdown
+rich_click.USE_MARKDOWN_EMOJI = True  # Parse emoji codes in markdown :smile:
+rich_click.USE_RICH_MARKUP = (
+    False  # Parse help strings for rich markup (eg. [red]my text[/])
+)
+rich_click.COMMAND_GROUPS = {}  # Define sorted groups of panels to display subcommands
+rich_click.OPTION_GROUPS = (
+    {}
+)  # Define sorted groups of panels to display options and arguments
+rich_click.USE_CLICK_SHORT_HELP = (
+    False  # Use click's default function to truncate help text
+)
diff --git a/src/fides/cli/commands/annotate.py b/src/fides/cli/commands/annotate.py
index 4c6e390bee..95460b82d4 100644
--- a/src/fides/cli/commands/annotate.py
+++ b/src/fides/cli/commands/annotate.py
@@ -1,6 +1,6 @@
 """Contains the annotate group of CLI commands for fides."""
 
-import click
+import rich_click as click
 
 from fides.cli.utils import with_analytics
 from fides.core import annotate_dataset as _annotate_dataset
@@ -10,7 +10,7 @@
 @click.pass_context
 def annotate(ctx: click.Context) -> None:
     """
-    Annotate fides resource types
+    Interactively annotate Fides resources.
     """
 
 
@@ -21,21 +21,21 @@ def annotate(ctx: click.Context) -> None:
     "-a",
     "--all-members",
     is_flag=True,
-    help="Annotate all dataset members, not just fields",
+    help="Annotate all parts of the dataset including schemas and tables.",
 )
 @click.option(
     "-v",
     "--validate",
     is_flag=True,
     default=False,
-    help="Strictly validate annotation inputs.",
+    help="Validate annotation inputs.",
 )
 @with_analytics
 def annotate_dataset(
     ctx: click.Context, input_filename: str, all_members: bool, validate: bool
 ) -> None:
     """
-    Guided flow for annotating datasets. The dataset file will be edited in-place.
+    Interactively annotate a dataset file in-place.
     """
     config = ctx.obj["CONFIG"]
     _annotate_dataset.annotate_dataset(
diff --git a/src/fides/cli/commands/core.py b/src/fides/cli/commands/core.py
index e929322fc7..7c80437d6e 100644
--- a/src/fides/cli/commands/core.py
+++ b/src/fides/cli/commands/core.py
@@ -1,14 +1,9 @@
 """Contains all of the core CLI commands for fides."""
 from typing import Optional
 
-import click
+import rich_click as click
 
-from fides.cli.options import (
-    dry_flag,
-    fides_key_option,
-    manifests_dir_argument,
-    verbose_flag,
-)
+from fides.cli.options import dry_flag, manifests_dir_argument, verbose_flag
 from fides.cli.utils import pretty_echo, print_divider, with_analytics
 from fides.core import audit as _audit
 from fides.core import evaluate as _evaluate
@@ -24,13 +19,13 @@
 @click.option(
     "--diff",
     is_flag=True,
-    help="Include any changes between server and local resources in the command output",
+    help="Print any diffs between the local & server objects",
 )
 @manifests_dir_argument
 @with_analytics
 def push(ctx: click.Context, dry: bool, diff: bool, manifests_dir: str) -> None:
     """
-    Validate local manifest files and persist any changes via the API server.
+    Parse local manifest files and upload them to the server.
     """
 
     config = ctx.obj["CONFIG"]
@@ -47,19 +42,28 @@ def push(ctx: click.Context, dry: bool, diff: bool, manifests_dir: str) -> None:
 @click.command()
 @click.pass_context
 @manifests_dir_argument
-@fides_key_option
+@click.option(
+    "--fides-key",
+    "-k",
+    help="The fides_key of a specific policy to evaluate.",
+    default="",
+)
 @click.option(
     "-m",
     "--message",
-    help="A message that you can supply to describe the context of this evaluation.",
+    help="Describe the context of this evaluation.",
 )
 @click.option(
     "-a",
     "--audit",
     is_flag=True,
-    help="Raise errors if resources are missing attributes required for building a data map.",
+    help="Validate that the objects in this evaluation produce a valid data map.",
+)
+@click.option(
+    "--dry",
+    is_flag=True,
+    help="Do not upload objects or results to the Fides webserver.",
 )
-@dry_flag
 @with_analytics
 def evaluate(
     ctx: click.Context,
@@ -70,12 +74,7 @@ def evaluate(
     dry: bool,
 ) -> None:
     """
-    Compare your System's Privacy Declarations with your Organization's Policy Rules.
-
-    All local resources are applied to the server before evaluation.
-
-    If your policy evaluation fails, it is expected that you will need to
-    either adjust your Privacy Declarations, Datasets, or Policies before trying again.
+    Evaluate System-level Privacy Declarations against Organization-level Policy Rules.
     """
 
     config = ctx.obj["CONFIG"]
@@ -127,10 +126,7 @@ def evaluate(
 @with_analytics
 def parse(ctx: click.Context, manifests_dir: str, verbose: bool = False) -> None:
     """
-    Reads the resource files that are stored in MANIFESTS_DIR and its subdirectories to verify
-    the validity of all manifest files.
-
-    If the taxonomy is invalid, this command prints the error messages and triggers a non-zero exit code.
+    Parse all Fides objects located in the supplied directory.
     """
     taxonomy = _parse.parse(manifests_dir=manifests_dir)
     if verbose:
@@ -149,12 +145,7 @@ def parse(ctx: click.Context, manifests_dir: str, verbose: bool = False) -> None
 @with_analytics
 def pull(ctx: click.Context, manifests_dir: str, all_resources: Optional[str]) -> None:
     """
-    Update local resource files by their fides_key to match their server versions.
-
-    Alternatively, with the "--all" flag all resources from the server will be pulled
-    down into a local file.
-
-    The pull is aborted if there are unstaged or untracked files in the manifests dir.
+    Update local resource files based on the state of the objects on the server.
     """
 
     # Make the resources that are pulled configurable
diff --git a/src/fides/cli/commands/crud.py b/src/fides/cli/commands/crud.py
index a2826fbcbc..cdd0578c67 100644
--- a/src/fides/cli/commands/crud.py
+++ b/src/fides/cli/commands/crud.py
@@ -1,12 +1,12 @@
 """Contains all of the CRUD-type CLI commands for fides."""
-import click
+import rich_click as click
 import yaml
 
 from fides.cli.options import fides_key_argument, resource_type_argument
 from fides.cli.utils import handle_cli_response, print_divider, with_analytics
 from fides.core import api as _api
 from fides.core.api_helpers import get_server_resource, list_server_resources
-from fides.core.utils import echo_green
+from fides.core.utils import echo_green, echo_red
 
 
 @click.command()
@@ -16,7 +16,7 @@
 @with_analytics
 def delete(ctx: click.Context, resource_type: str, fides_key: str) -> None:
     """
-    Delete a resource on the server.
+    Delete an object from the server.
     """
     config = ctx.obj["CONFIG"]
     handle_cli_response(
@@ -25,7 +25,11 @@ def delete(ctx: click.Context, resource_type: str, fides_key: str) -> None:
             resource_type=resource_type,
             resource_id=fides_key,
             headers=config.user.auth_header,
-        )
+        ),
+        verbose=False,
+    )
+    echo_green(
+        f"{resource_type.capitalize()} with fides_key '{fides_key}' successfully deleted."
     )
 
 
@@ -36,7 +40,7 @@ def delete(ctx: click.Context, resource_type: str, fides_key: str) -> None:
 @with_analytics
 def get_resource(ctx: click.Context, resource_type: str, fides_key: str) -> None:
     """
-    View a resource from the server as a YAML object.
+    View an object from the server.
     """
     config = ctx.obj["CONFIG"]
     resource = get_server_resource(
@@ -54,9 +58,12 @@ def get_resource(ctx: click.Context, resource_type: str, fides_key: str) -> None
 @click.pass_context
 @resource_type_argument
 @with_analytics
-def list_resources(ctx: click.Context, resource_type: str) -> None:
+@click.option(
+    "--verbose", "-v", is_flag=True, help="Displays the entire object list as YAML."
+)
+def list_resources(ctx: click.Context, verbose: bool, resource_type: str) -> None:
     """
-    Get a list of all resources of this type from the server and display them as YAML.
+    View all objects of a single type from the server.
     """
     config = ctx.obj["CONFIG"]
     resources = list_server_resources(
@@ -67,4 +74,14 @@ def list_resources(ctx: click.Context, resource_type: str) -> None:
         raw=True,
     )
     print_divider()
-    echo_green(yaml.dump({resource_type: resources}))
+    if verbose:
+        echo_green(yaml.dump({resource_type: resources}))
+    else:
+        if resources:
+            sorted_fides_keys = sorted(
+                {resource["fides_key"] for resource in resources if resource}
+            )
+            formatted_fides_keys = "\n  ".join(sorted_fides_keys)
+            echo_green(f"{resource_type.capitalize()} list:\n  {formatted_fides_keys}")
+        else:
+            echo_red(f"No {resource_type.capitalize()} resources found!")
diff --git a/src/fides/cli/commands/db.py b/src/fides/cli/commands/db.py
index 7f27a466a7..0d8d45faeb 100644
--- a/src/fides/cli/commands/db.py
+++ b/src/fides/cli/commands/db.py
@@ -1,5 +1,5 @@
 """Contains the db group of the commands for fides."""
-import click
+import rich_click as click
 
 from fides.cli.options import yes_flag
 from fides.cli.utils import handle_cli_response, with_analytics
@@ -11,7 +11,7 @@
 @click.pass_context
 def database(ctx: click.Context) -> None:
     """
-    Database utility commands
+    Run actions against the application database.
     """
 
 
@@ -20,7 +20,7 @@ def database(ctx: click.Context) -> None:
 @with_analytics
 def db_init(ctx: click.Context) -> None:
     """
-    Initialize the fides database.
+    Initialize the Fides database.
     """
     config = ctx.obj["CONFIG"]
     handle_cli_response(
@@ -38,7 +38,7 @@ def db_init(ctx: click.Context) -> None:
 @with_analytics
 def db_reset(ctx: click.Context, yes: bool) -> None:
     """
-    Wipes all user-created data and resets the database back to its freshly initialized state.
+    Reset the database back to its initial state.
     """
     config = ctx.obj["CONFIG"]
     if yes:
diff --git a/src/fides/cli/commands/export.py b/src/fides/cli/commands/export.py
index cc6daebb39..5d6879f944 100644
--- a/src/fides/cli/commands/export.py
+++ b/src/fides/cli/commands/export.py
@@ -1,5 +1,5 @@
 """Contains the export group of CLI commands for fides."""
-import click
+import rich_click as click
 
 from fides.cli.options import (
     dry_flag,
@@ -16,7 +16,7 @@
 @click.pass_context
 def export(ctx: click.Context) -> None:
     """
-    Export fides resource types
+    Export Fides data maps.
     """
 
 
@@ -31,7 +31,7 @@ def export_system(
     dry: bool,
 ) -> None:
     """
-    Export a system in a data map format.
+    Export systems in a data map format.
     """
     config = ctx.obj["CONFIG"]
     taxonomy = _parse.parse(manifests_dir)
@@ -55,7 +55,7 @@ def export_dataset(
     dry: bool,
 ) -> None:
     """
-    Export a dataset in a data map format.
+    Export datasets in a data map format.
     """
     config = ctx.obj["CONFIG"]
     taxonomy = _parse.parse(manifests_dir)
@@ -79,7 +79,7 @@ def export_organization(
     dry: bool,
 ) -> None:
     """
-    Export an organization in a data map format.
+    Export organizations in a data map format.
     """
     config = ctx.obj["CONFIG"]
     taxonomy = _parse.parse(manifests_dir)
@@ -111,17 +111,9 @@ def export_datamap(
     csv: bool,
 ) -> None:
     """
-    Export a formatted data map to excel using the fides template.
+    Export a data map using the standard Fides template.
 
     The data map is comprised of an Organization, Systems, and Datasets.
-
-    The default organization is used, however a custom one can be
-    passed if required.
-
-    A custom manifest directory can be provided for the output location.
-
-    The csv flag can be used to output data as csv, while the dry
-    flag can be used to return data to the console instead.
     """
     config = ctx.obj["CONFIG"]
     _export.export_datamap(
diff --git a/src/fides/cli/commands/generate.py b/src/fides/cli/commands/generate.py
index edb5036853..5cd8d64392 100644
--- a/src/fides/cli/commands/generate.py
+++ b/src/fides/cli/commands/generate.py
@@ -1,5 +1,5 @@
 """Contains the generate group of CLI commands for fides."""
-import click
+import rich_click as click
 
 from fides.cli.options import (
     aws_access_key_id_option,
@@ -27,7 +27,7 @@
 @click.pass_context
 def generate(ctx: click.Context) -> None:
     """
-    Generate fides resource types
+    Programmatically generate Fides objects.
     """
 
 
@@ -35,7 +35,7 @@ def generate(ctx: click.Context) -> None:
 @click.pass_context
 def generate_dataset(ctx: click.Context) -> None:
     """
-    Generate fides Dataset resources
+    Generate Fides datasets.
     """
 
 
@@ -54,13 +54,7 @@ def generate_dataset_db(
     include_null: bool,
 ) -> None:
     """
-    Connect to a database directly via a SQLAlchemy-style connection string and
-    generate a dataset manifest file that consists of every schema/table/field.
-    Connection string can be supplied as an option or a credentials reference
-    to fides config.
-
-    This is a one-time operation that does not track the state of the database.
-    It will need to be run again if the database schema changes.
+    Generate a Fides dataset by walking a database and recording every schema/table/field.
     """
     actual_connection_string = handle_database_credentials_options(
         fides_config=ctx.obj["CONFIG"],
@@ -79,7 +73,7 @@ def generate_dataset_db(
 @click.pass_context
 def generate_dataset_gcp(ctx: click.Context) -> None:
     """
-    Generate fides Dataset resources for Google Cloud Platform
+    Generate Fides datasets from Google Cloud Platform.
     """
 
 
@@ -100,13 +94,7 @@ def generate_dataset_bigquery(
     include_null: bool,
 ) -> None:
     """
-    Connect to a BigQuery dataset directly via a SQLAlchemy connection and
-    generate a dataset manifest file that consists of every schema/table/field.
-    A path to a google authorization keyfile can be supplied as an option, or a
-    credentials reference to fides config.
-
-    This is a one-time operation that does not track the state of the dataset.
-    It will need to be run again if the dataset schema changes.
+    Generate a dataset object from BigQuery using a SQLAlchemy connection string.
     """
 
     bigquery_config = handle_bigquery_config_options(
@@ -127,7 +115,7 @@ def generate_dataset_bigquery(
 @click.pass_context
 def generate_system(ctx: click.Context) -> None:
     """
-    Generate fides System resources
+    Generate Fides systems.
     """
 
 
@@ -150,13 +138,8 @@ def generate_system_okta(
     org_key: str,
 ) -> None:
     """
-    Generates systems for your Okta applications. Connect to an Okta admin
-    account by providing an organization url and auth token or a credentials
-    reference to fides config. Auth token and organization url can also
-    be supplied by setting environment variables as defined by the okta python sdk.
-
-    This is a one-time operation that does not track the state of the okta resources.
-    It will need to be run again if the tracked resources change.
+    Generates systems from your Okta applications. Connects via
+    an Okta admin account.
     """
     config = ctx.obj["CONFIG"]
     okta_config = handle_okta_credentials_options(
@@ -199,12 +182,6 @@ def generate_system_aws(
     """
     Connect to an aws account and generate a system manifest file that consists of every
     tracked resource.
-    Credentials can be supplied as options, a credentials
-    reference to fides config, or boto3 environment configuration.
-    Tracked resources: [Redshift, RDS, DynamoDb, S3]
-
-    This is a one-time operation that does not track the state of the aws resources.
-    It will need to be run again if the tracked resources change.
     """
     config = ctx.obj["CONFIG"]
     aws_config = handle_aws_credentials_options(
diff --git a/src/fides/cli/commands/scan.py b/src/fides/cli/commands/scan.py
index 5fa89e3f84..9782069b01 100644
--- a/src/fides/cli/commands/scan.py
+++ b/src/fides/cli/commands/scan.py
@@ -1,6 +1,6 @@
 """Contains the scan group of the commands for fides."""
 
-import click
+import rich_click as click
 
 from fides.cli.options import (
     aws_access_key_id_option,
@@ -28,7 +28,7 @@
 @click.pass_context
 def scan(ctx: click.Context) -> None:
     """
-    Scan external resource coverage against fides resources
+    Scan and report on discrepancies between Fides resource files and real infrastructure.
     """
 
 
@@ -36,7 +36,7 @@ def scan(ctx: click.Context) -> None:
 @click.pass_context
 def scan_dataset(ctx: click.Context) -> None:
     """
-    Scan fides Dataset resources
+    Scan and report on Fides Dataset resources.
     """
 
 
@@ -55,15 +55,10 @@ def scan_dataset_db(
     coverage_threshold: int,
 ) -> None:
     """
-    Connect to a database directly via a SQLAlchemy-style connection string and
-    compare the database objects to existing datasets. Connection string can be
-    supplied as an option or a credentials reference to fides config.
+    Scan a database directly using a SQLAlchemy-style connection string.
 
-    If there are fields within the database that aren't listed and categorized
-    within one of the datasets, this counts as lacking coverage.
-
-    Outputs missing fields and has a non-zero exit if coverage is
-    under the stated threshold.
+    _If there are fields within the database that aren't listed and categorized
+    within one of the datasets, this counts as lacking coverage._
     """
     config = ctx.obj["CONFIG"]
     actual_connection_string = handle_database_credentials_options(
@@ -85,7 +80,7 @@ def scan_dataset_db(
 @click.pass_context
 def scan_system(ctx: click.Context) -> None:
     """
-    Scan fides System resources
+    Scan and report on Fides System resources.
     """
 
 
@@ -108,14 +103,7 @@ def scan_system_okta(
     coverage_threshold: int,
 ) -> None:
     """
-    Scans your existing systems and compares them to found Okta applications.
-    Connect to an Okta admin account by providing an organization url and
-    auth token or a credentials reference to fides config. Auth token and
-    organization url can also be supplied by setting environment variables
-    as defined by the okta python sdk.
-
-    Outputs missing resources and has a non-zero exit if coverage is
-    under the stated threshold.
+    Scan an Okta account and compare applications with annotated Fides Systems.
     """
 
     config = ctx.obj["CONFIG"]
@@ -154,13 +142,9 @@ def scan_system_aws(
     coverage_threshold: int,
 ) -> None:
     """
-    Connect to an aws account and compares tracked resources to existing systems.
-    Credentials can be supplied as options, a credentials reference to fides
-    config, or boto3 environment configuration.
-    Tracked resources: [Redshift, RDS, DynamoDb, S3]
+    Scan an AWS account and compare objects with annotated Fides Systems.
 
-    Outputs missing resources and has a non-zero exit if coverage is
-    under the stated threshold.
+    _Scannable resources: [Redshift, RDS, DynamoDb, S3]_
     """
     config = ctx.obj["CONFIG"]
     aws_config = handle_aws_credentials_options(
diff --git a/src/fides/cli/commands/user.py b/src/fides/cli/commands/user.py
index 773712e547..395b1b7759 100644
--- a/src/fides/cli/commands/user.py
+++ b/src/fides/cli/commands/user.py
@@ -1,5 +1,5 @@
 """Contains the user command group for the fides CLI."""
-import click
+import rich_click as click
 
 from fides.cli.options import (
     first_name_option,
@@ -28,9 +28,7 @@ def create(
     ctx: click.Context, username: str, password: str, first_name: str, last_name: str
 ) -> None:
     """
-    Use credentials from the credentials file to create a new user.
-
-    Gives full permissions to the new user.
+    Use the credentials file to create a new user. Gives full permissions to the new user.
     """
     config = ctx.obj["CONFIG"]
     server_url = config.cli.server_url
@@ -49,7 +47,7 @@ def create(
 @password_option
 def login(ctx: click.Context, username: str, password: str) -> None:
     """
-    Use credentials to get a user access token and write it to a credentials file.
+    Generate a user access token and write it to a credentials file.
     """
     config = ctx.obj["CONFIG"]
     server_url = config.cli.server_url
@@ -59,7 +57,9 @@ def login(ctx: click.Context, username: str, password: str) -> None:
 @user.command(name="permissions")
 @click.pass_context
 def get_permissions(ctx: click.Context) -> None:
-    """List the directly-assigned scopes and roles available to the current user."""
+    """
+    List the directly-assigned scopes and roles available to the current user.
+    """
     config = ctx.obj["CONFIG"]
     server_url = config.cli.server_url
     get_permissions_command(server_url=server_url)
diff --git a/src/fides/cli/commands/util.py b/src/fides/cli/commands/util.py
index 2c1acc2475..f0e10df194 100644
--- a/src/fides/cli/commands/util.py
+++ b/src/fides/cli/commands/util.py
@@ -2,7 +2,7 @@
 from datetime import datetime, timezone
 from subprocess import CalledProcessError
 
-import click
+import rich_click as click
 
 import fides
 from fides.cli.utils import (
@@ -28,16 +28,14 @@
 
 @click.command()
 @click.pass_context
-@click.argument("fides_directory_location", default=".", type=click.Path(exists=True))
+@click.argument("fides_dir", default=".", type=click.Path(exists=True))
 @click.option(
     "--opt-in", is_flag=True, help="Automatically opt-in to anonymous usage analytics."
 )
-def init(ctx: click.Context, fides_directory_location: str, opt_in: bool) -> None:
+def init(ctx: click.Context, fides_dir: str, opt_in: bool) -> None:
     """
-    Initializes a fides instance, creating the default directory (`.fides/`) and
-    the configuration file (`fides.toml`) if necessary.
-
-    Additionally, requests the ability to respectfully collect anonymous usage data.
+    Initializes a Fides instance by creating the default directory and
+    configuration file if not present.
     """
 
     executed_at = datetime.now(timezone.utc)
@@ -47,7 +45,7 @@ def init(ctx: click.Context, fides_directory_location: str, opt_in: bool) -> Non
     click.echo("Initializing fides...")
 
     config, config_path = create_and_update_config_file(
-        config, fides_directory_location, opt_in=opt_in
+        config, fides_dir, opt_in=opt_in
     )
 
     print_divider()
@@ -61,7 +59,7 @@ def init(ctx: click.Context, fides_directory_location: str, opt_in: bool) -> Non
 @with_analytics
 def status(ctx: click.Context) -> None:
     """
-    Sends a request to the fides API healthcheck endpoint and prints the response.
+    Check Fides server availability.
     """
     config = ctx.obj["CONFIG"]
     cli_version = fides.__version__
@@ -78,7 +76,9 @@ def status(ctx: click.Context) -> None:
 @click.option("--port", "-p", type=int, default=8080)
 def webserver(ctx: click.Context, port: int = 8080) -> None:
     """
-    Starts the fides API server using Uvicorn.
+    Start the Fides webserver.
+
+    _Requires Redis and Postgres to be configured and running_
     """
     # This has to be here to avoid a circular dependency
     from fides.api.main import start_webserver
@@ -91,7 +91,7 @@ def webserver(ctx: click.Context, port: int = 8080) -> None:
 @with_analytics
 def worker(ctx: click.Context) -> None:
     """
-    Starts a celery worker.
+    Start a Celery worker for the Fides webserver.
     """
     # This has to be here to avoid a circular dependency
     from fides.api.ops.worker import start_worker
@@ -123,9 +123,11 @@ def deploy(ctx: click.Context) -> None:
     is_flag=True,
     help="Disable the initialization of the Fides CLI, to run in headless mode.",
 )
-def up(ctx: click.Context, no_pull: bool = False, no_init: bool = False) -> None:
+def up(
+    ctx: click.Context, no_pull: bool = False, no_init: bool = False
+) -> None:  # pragma: no cover
     """
-    Starts the sample project via docker compose.
+    Starts a sample project via docker compose.
     """
 
     check_virtualenv()
@@ -138,7 +140,9 @@ def up(ctx: click.Context, no_pull: bool = False, no_init: bool = False) -> None
 
     try:
         check_fides_uploads_dir()
+        print("> Starting application...")
         start_application()
+        print("> Seeding data...")
         seed_example_data()
         click.clear()
 
diff --git a/src/fides/cli/commands/view.py b/src/fides/cli/commands/view.py
index fde0ab432c..c8711f53a3 100644
--- a/src/fides/cli/commands/view.py
+++ b/src/fides/cli/commands/view.py
@@ -1,9 +1,10 @@
 """Contains the view group of the commands for fides."""
 
-import click
-from toml import dumps as toml_dumps
+import rich_click as click
+from toml import dumps
 
 from fides.cli.utils import print_divider, with_analytics
+from fides.core.utils import echo_red, get_credentials_path, read_credentials_file
 
 
 @click.group(name="view")
@@ -27,7 +28,9 @@ def view_config(
     ctx: click.Context, section: str = "", exclude_unset: bool = False
 ) -> None:
     """
-    Prints the configuration values being used.
+    Prints the configuration values being used for this command-line instance.
+
+    _Note: To see the configuration values being used by the webserver, `GET` the `/api/v1/config` endpoint._
     """
     config = ctx.obj["CONFIG"]
     config_dict = config.dict(exclude_unset=exclude_unset)
@@ -35,4 +38,22 @@ def view_config(
         config_dict = config_dict[section]
 
     print_divider()
-    print(toml_dumps(config_dict))
+    print(dumps(config_dict))
+
+
+@view.command(name="credentials")
+@click.pass_context
+@with_analytics
+def view_credentials(ctx: click.Context) -> None:
+    """
+    Prints the credentials file.
+    """
+    credentials_path = get_credentials_path()
+    try:
+        credentials = read_credentials_file(credentials_path)
+    except FileNotFoundError:
+        echo_red(f"No credentials file found at path: {credentials_path}")
+        raise SystemExit(1)
+
+    print_divider()
+    print(dumps(credentials.dict()))
diff --git a/src/fides/cli/options.py b/src/fides/cli/options.py
index 5700f3ec83..6da30ac6c9 100644
--- a/src/fides/cli/options.py
+++ b/src/fides/cli/options.py
@@ -1,17 +1,21 @@
 """
-Contains all of the options/arguments used by the CLI commands.
+Reusable command-line arguments and options.
 """
 
 from typing import Callable
 
-import click
+import rich_click as click
 from fideslang import model_list
 
 
 def coverage_threshold_option(command: Callable) -> Callable:
-    "Add a flag that assumes yes."
+    """An option decorator that sets a required coverage percentage."""
     command = click.option(
-        "--coverage-threshold", "-c", type=click.IntRange(0, 100), default=100
+        "--coverage-threshold",
+        "-c",
+        type=click.IntRange(0, 100),
+        default=100,
+        help="Set the coverage percentage for a passing scan.",
     )(command)
     return command
 
@@ -40,7 +44,6 @@ def fides_key_option(command: Callable) -> Callable:
         "-k",
         "--fides-key",
         default="",
-        help="The fides_key of the single policy that you wish to evaluate.",
     )(command)
     return command
 
@@ -48,9 +51,7 @@ def fides_key_option(command: Callable) -> Callable:
 def manifests_dir_argument(command: Callable) -> Callable:
     "Add the manifests_dir argument."
     command = click.argument(
-        "manifests_dir",
-        default=".fides/",
-        type=click.Path(exists=True),
+        "manifests_dir", type=click.Path(exists=True), default=".fides/"
     )(command)
     return command
 
@@ -58,7 +59,7 @@ def manifests_dir_argument(command: Callable) -> Callable:
 def dry_flag(command: Callable) -> Callable:
     "Add a flag that prevents side-effects."
     command = click.option(
-        "--dry", is_flag=True, help="Prevent the persistance of any changes."
+        "--dry", is_flag=True, help="Do not upload results to the Fides webserver."
     )(command)
     return command
 
@@ -69,7 +70,7 @@ def yes_flag(command: Callable) -> Callable:
         "--yes",
         "-y",
         is_flag=True,
-        help="Automatically responds 'yes' to any prompts.",
+        help="Automatically responds `yes` to any prompts.",
     )(command)
     return command
 
@@ -90,7 +91,7 @@ def include_null_flag(command: Callable) -> Callable:
     command = click.option(
         "--include-null",
         is_flag=True,
-        help="Includes attributes that would otherwise be null.",
+        help="Include null attributes.",
     )(command)
     return command
 
@@ -101,7 +102,8 @@ def organization_fides_key_option(command: Callable) -> Callable:
         "--org-key",
         "-k",
         default="default_organization",
-        help="The organization_fides_key you wish to export resources for.",
+        show_default=True,
+        help="The `organization_fides_key` of the `Organization` you want to specify.",
     )(command)
     return command
 
@@ -112,6 +114,7 @@ def output_directory_option(command: Callable) -> Callable:
         "--output-dir",
         "-d",
         default=".fides/",
+        show_default=True,
         help="The output directory for the data map to be exported to.",
     )(command)
     return command
@@ -122,7 +125,7 @@ def credentials_id_option(command: Callable) -> Callable:
     command = click.option(
         "--credentials-id",
         type=str,
-        help="Use credentials defined within fides config",
+        help="Use credentials keys defined within Fides config.",
     )(command)
     return command
 
@@ -132,7 +135,7 @@ def connection_string_option(command: Callable) -> Callable:
     command = click.option(
         "--connection-string",
         type=str,
-        help="Use connection string option to connect to a database",
+        help="Use the connection string option to connect to a database.",
     )(command)
     return command
 
@@ -142,7 +145,7 @@ def okta_org_url_option(command: Callable) -> Callable:
     command = click.option(
         "--org-url",
         type=str,
-        help="Use org url option to connect to okta. Requires options --org-url and --token",
+        help="Connect to Okta using an 'Org URL'. _Requires options `--org-url` & `--token`._",
     )(command)
     return command
 
@@ -152,7 +155,7 @@ def okta_token_option(command: Callable) -> Callable:
     command = click.option(
         "--token",
         type=str,
-        help="Use token option to connect to okta. Requires options --org-url and --token",
+        help="Connect to Okta using a token. _Requires options `--org-url` and `--token`._",
     )(command)
     return command
 
@@ -162,7 +165,7 @@ def aws_access_key_id_option(command: Callable) -> Callable:
     command = click.option(
         "--access_key_id",
         type=str,
-        help="Use access key id option to connect to aws. Requires options --access_key_id, --secret_access_key and --region",
+        help="Connect to AWS using an `Access Key ID`. _Requires options `--access_key_id`, `--secret_access_key` & `--region`._",
     )(command)
     return command
 
@@ -172,7 +175,7 @@ def aws_secret_access_key_option(command: Callable) -> Callable:
     command = click.option(
         "--secret_access_key",
         type=str,
-        help="Use access key option to connect to aws. Requires options --access_key_id, --secret_access_key and --region",
+        help="Connect to AWS using an `Access Key`. _Requires options `--access_key_id`, `--secret_access_key` & `--region`._",
     )(command)
     return command
 
@@ -182,7 +185,7 @@ def aws_region_option(command: Callable) -> Callable:
     command = click.option(
         "--region",
         type=str,
-        help="Use region option to connect to aws. Requires options --access_key_id, --secret_access_key and --region",
+        help="Connect to AWS using a specific `Region`. _Requires options `--access_key_id`, `--secret_access_key` & `--region`._",
     )(command)
     return command
 
diff --git a/src/fides/cli/utils.py b/src/fides/cli/utils.py
index c0efbe22a6..5c7ec76e7a 100644
--- a/src/fides/cli/utils.py
+++ b/src/fides/cli/utils.py
@@ -10,8 +10,8 @@
 from platform import system
 from typing import Any, Callable, Dict, Optional, Union
 
-import click
 import requests
+import rich_click as click
 from fideslog.sdk.python.client import AnalyticsClient
 from fideslog.sdk.python.event import AnalyticsEvent
 from fideslog.sdk.python.exceptions import AnalyticsError
diff --git a/tests/ctl/cli/test_cli.py b/tests/ctl/cli/test_cli.py
index 5de3f9841e..53e2b2e241 100644
--- a/tests/ctl/cli/test_cli.py
+++ b/tests/ctl/cli/test_cli.py
@@ -51,13 +51,22 @@ def test_init_opt_in(test_cli_runner: CliRunner) -> None:
     assert result.exit_code == 0
 
 
-@pytest.mark.unit
-def test_view_config(test_cli_runner: CliRunner) -> None:
-    result = test_cli_runner.invoke(
-        cli, ["view", "config"], env={"FIDES__USER__ANALYTICS_OPT_OUT": "true"}
-    )
-    print(result.output)
-    assert result.exit_code == 0
+class TestView:
+    @pytest.mark.unit
+    def test_view_config(self, test_cli_runner: CliRunner) -> None:
+        result = test_cli_runner.invoke(
+            cli, ["view", "config"], env={"FIDES__USER__ANALYTICS_OPT_OUT": "true"}
+        )
+        print(result.output)
+        assert result.exit_code == 0
+
+    @pytest.mark.unit
+    def test_view_credentials(self, test_cli_runner: CliRunner) -> None:
+        result = test_cli_runner.invoke(
+            cli, ["view", "credentials"], env={"FIDES__USER__ANALYTICS_OPT_OUT": "true"}
+        )
+        print(result.output)
+        assert result.exit_code == 0
 
 
 @pytest.mark.unit
@@ -197,8 +206,8 @@ def test_audit(test_config_path: str, test_cli_runner: CliRunner) -> None:
     assert result.exit_code == 0
 
 
+@pytest.mark.integration
 class TestCRUD:
-    @pytest.mark.integration
     def test_get(self, test_config_path: str, test_cli_runner: CliRunner) -> None:
         result = test_cli_runner.invoke(
             cli,
@@ -207,12 +216,36 @@ def test_get(self, test_config_path: str, test_cli_runner: CliRunner) -> None:
         print(result.output)
         assert result.exit_code == 0
 
-    @pytest.mark.integration
+    def test_delete(self, test_config_path: str, test_cli_runner: CliRunner) -> None:
+        result = test_cli_runner.invoke(
+            cli,
+            ["-f", test_config_path, "delete", "system", "demo_marketing_system"],
+        )
+        print(result.output)
+        assert result.exit_code == 0
+
     def test_ls(self, test_config_path: str, test_cli_runner: CliRunner) -> None:
         result = test_cli_runner.invoke(cli, ["-f", test_config_path, "ls", "system"])
         print(result.output)
         assert result.exit_code == 0
 
+    def test_ls_verbose(
+        self, test_config_path: str, test_cli_runner: CliRunner
+    ) -> None:
+        result = test_cli_runner.invoke(
+            cli, ["-f", test_config_path, "ls", "system", "--verbose"]
+        )
+        print(result.output)
+        assert result.exit_code == 0
+
+    def test_ls_no_resources_found(
+        self, test_config_path: str, test_cli_runner: CliRunner
+    ) -> None:
+        """This test only workss because we don't have any registry resources by default."""
+        result = test_cli_runner.invoke(cli, ["-f", test_config_path, "ls", "registry"])
+        print(result.output)
+        assert result.exit_code == 0
+
 
 class TestEvaluate:
     @pytest.mark.integration