diff --git a/tests/assets/cli/multi_app.py b/tests/assets/cli/multi_app.py
index 1442aa2442..2c3e33ae26 100644
--- a/tests/assets/cli/multi_app.py
+++ b/tests/assets/cli/multi_app.py
@@ -13,14 +13,14 @@ def hello(name: str = "World", age: int = typer.Option(0, help="The age of the u
     typer.echo(f"Hello {name}")
 
 
-@sub_app.command()
+@sub_app.command(rich_help_panel="Greet")
 def hi(user: str = typer.Argument("World", help="The name of the user to greet")):
     """
     Say Hi
     """
 
 
-@sub_app.command()
+@sub_app.command(rich_help_panel="Farewell")
 def bye():
     """
     Say bye
@@ -32,7 +32,7 @@ def bye():
 app.add_typer(sub_app, name="sub")
 
 
-@app.command()
+@app.command(rich_help_panel="")
 def top():
     """
     Top command
diff --git a/tests/assets/cli/multiapp-docs-norich.md b/tests/assets/cli/multiapp-docs-norich.md
new file mode 100644
index 0000000000..67d02568db
--- /dev/null
+++ b/tests/assets/cli/multiapp-docs-norich.md
@@ -0,0 +1,102 @@
+# `multiapp`
+
+Demo App
+
+**Usage**:
+
+```console
+$ multiapp [OPTIONS] COMMAND [ARGS]...
+```
+
+**Options**:
+
+* `--install-completion`: Install completion for the current shell.
+* `--show-completion`: Show completion for the current shell, to copy it or customize the installation.
+* `--help`: Show this message and exit.
+
+The end
+
+**Commands**:
+
+* `top`: Top command
+* `sub`
+
+## `multiapp top`
+
+Top command
+
+**Usage**:
+
+```console
+$ multiapp top [OPTIONS]
+```
+
+**Options**:
+
+* `--help`: Show this message and exit.
+
+## `multiapp sub`
+
+**Usage**:
+
+```console
+$ multiapp sub [OPTIONS] COMMAND [ARGS]...
+```
+
+**Options**:
+
+* `--help`: Show this message and exit.
+
+**Commands**:
+
+* `hello`: Say Hello
+* `hi`: Say Hi
+* `bye`: Say bye
+
+### `multiapp sub hello`
+
+Say Hello
+
+**Usage**:
+
+```console
+$ multiapp sub hello [OPTIONS]
+```
+
+**Options**:
+
+* `--name TEXT`: [default: World]
+* `--age INTEGER`: The age of the user  [default: 0]
+* `--help`: Show this message and exit.
+
+### `multiapp sub hi`
+
+Say Hi
+
+**Usage**:
+
+```console
+$ multiapp sub hi [OPTIONS] [USER]
+```
+
+**Arguments**:
+
+* `[USER]`: The name of the user to greet  [default: World]
+
+**Options**:
+
+* `--help`: Show this message and exit.
+
+### `multiapp sub bye`
+
+Say bye
+
+**Usage**:
+
+```console
+$ multiapp sub bye [OPTIONS]
+```
+
+**Options**:
+
+* `--help`: Show this message and exit.
diff --git a/tests/assets/cli/multiapp-docs-title.md b/tests/assets/cli/multiapp-docs-title.md
index ffde843736..8c2f941c79 100644
--- a/tests/assets/cli/multiapp-docs-title.md
+++ b/tests/assets/cli/multiapp-docs-title.md
@@ -50,7 +50,13 @@ $ multiapp sub [OPTIONS] COMMAND [ARGS]...
 **Commands**:
 
 * `hello`: Say Hello
+
+**Greet**:
+
 * `hi`: Say Hi
+
+**Farewell**:
+
 * `bye`: Say bye
 
 ### `multiapp sub hello`
diff --git a/tests/assets/cli/multiapp-docs.md b/tests/assets/cli/multiapp-docs.md
index 67d02568db..d02c4d5187 100644
--- a/tests/assets/cli/multiapp-docs.md
+++ b/tests/assets/cli/multiapp-docs.md
@@ -50,7 +50,13 @@ $ multiapp sub [OPTIONS] COMMAND [ARGS]...
 **Commands**:
 
 * `hello`: Say Hello
+
+**Greet**:
+
 * `hi`: Say Hi
+
+**Farewell**:
+
 * `bye`: Say bye
 
 ### `multiapp sub hello`
diff --git a/tests/test_cli/test_doc.py b/tests/test_cli/test_doc.py
index 1da8bb73ef..439685225b 100644
--- a/tests/test_cli/test_doc.py
+++ b/tests/test_cli/test_doc.py
@@ -104,7 +104,9 @@ def test_doc_no_rich():
         capture_output=True,
         encoding="utf-8",
     )
-    docs_path: Path = Path(__file__).parent.parent / "assets/cli/multiapp-docs.md"
+    docs_path: Path = (
+        Path(__file__).parent.parent / "assets/cli/multiapp-docs-norich.md"
+    )
     docs = docs_path.read_text()
     assert docs in result.stdout
     assert "**Arguments**" in result.stdout
@@ -138,7 +140,7 @@ def test_doc_no_typer():
             "run",
             "-m",
             "typer",
-            "tests/assets/cli/empty_script.py",
+            "tests.assets.cli.empty_script",
             "utils",
             "docs",
         ],
diff --git a/typer/cli.py b/typer/cli.py
index 4b4356f8bd..6be6bed338 100644
--- a/typer/cli.py
+++ b/typer/cli.py
@@ -1,6 +1,8 @@
 import importlib.util
 import re
 import sys
+from collections import defaultdict
+from itertools import chain
 from pathlib import Path
 from typing import Any
 
@@ -244,26 +246,50 @@ def get_docs_for_click(
     if isinstance(obj, Group):
         group = obj
         commands = group.list_commands(ctx)
+        default_panel_name = "Commands"
+        if HAS_RICH:
+            from . import rich_utils
+
+            default_panel_name = rich_utils.COMMANDS_PANEL_TITLE
         if commands:
-            docs += "**Commands**:\n\n"
+            panel_to_commands: dict[str, list[click.Command]] = defaultdict(list)
             for command in commands:
                 command_obj = group.get_command(ctx, command)
                 assert command_obj
-                docs += f"* `{command_obj.name}`"
-                command_help = command_obj.get_short_help_str()
-                if command_help:
-                    docs += f": {_parse_html(to_parse, command_help)}"
+                panel_name = default_panel_name
+                if HAS_RICH:
+                    from . import rich_utils
+
+                    panel_name = rich_utils.get_panel_name(
+                        command_obj, default_panel_name
+                    )
+                panel_to_commands[panel_name].append(command_obj)
+            if HAS_RICH:
+                # Ensure that the ungrouped commands show up first
+                default_command_objs = panel_to_commands.pop(default_panel_name, [])
+                if len(default_command_objs) > 0:
+                    panel_to_commands = {
+                        default_panel_name: default_command_objs,
+                        **panel_to_commands,
+                    }
+            for panel_name, command_objs in panel_to_commands.items():
+                docs += f"**{panel_name}**:\n\n"
+                for command_obj in command_objs:
+                    docs += f"* `{command_obj.name}`"
+                    command_help = command_obj.get_short_help_str()
+                    if command_help:
+                        docs += f": {_parse_html(to_parse, command_help)}"
+                    docs += "\n"
                 docs += "\n"
-            docs += "\n"
-        for command in commands:
-            command_obj = group.get_command(ctx, command)
-            assert command_obj
-            use_prefix = ""
-            if command_name:
-                use_prefix += f"{command_name}"
-            docs += get_docs_for_click(
-                obj=command_obj, ctx=ctx, indent=indent + 1, call_prefix=use_prefix
-            )
+            for command_obj in chain.from_iterable(
+                command_objs for command_objs in panel_to_commands.values()
+            ):
+                use_prefix = ""
+                if command_name:
+                    use_prefix += f"{command_name}"
+                docs += get_docs_for_click(
+                    obj=command_obj, ctx=ctx, indent=indent + 1, call_prefix=use_prefix
+                )
     return docs
 
 
diff --git a/typer/rich_utils.py b/typer/rich_utils.py
index d85043238c..c1519684e4 100644
--- a/typer/rich_utils.py
+++ b/typer/rich_utils.py
@@ -575,14 +575,10 @@ def rich_format_help(
         if getattr(param, "hidden", False):
             continue
         if isinstance(param, click.Argument):
-            panel_name = (
-                getattr(param, _RICH_HELP_PANEL_NAME, None) or ARGUMENTS_PANEL_TITLE
-            )
+            panel_name = get_panel_name(param, ARGUMENTS_PANEL_TITLE)
             panel_to_arguments[panel_name].append(param)
         elif isinstance(param, click.Option):
-            panel_name = (
-                getattr(param, _RICH_HELP_PANEL_NAME, None) or OPTIONS_PANEL_TITLE
-            )
+            panel_name = get_panel_name(param, OPTIONS_PANEL_TITLE)
             panel_to_options[panel_name].append(param)
     default_arguments = panel_to_arguments.get(ARGUMENTS_PANEL_TITLE, [])
     _print_options_panel(
@@ -628,10 +624,7 @@ def rich_format_help(
         for command_name in obj.list_commands(ctx):
             command = obj.get_command(ctx, command_name)
             if command and not command.hidden:
-                panel_name = (
-                    getattr(command, _RICH_HELP_PANEL_NAME, None)
-                    or COMMANDS_PANEL_TITLE
-                )
+                panel_name = get_panel_name(command, COMMANDS_PANEL_TITLE)
                 panel_to_commands[panel_name].append(command)
 
         # Identify the longest command name in all panels
@@ -751,3 +744,9 @@ def get_traceback(
         width=MAX_WIDTH,
     )
     return rich_tb
+
+
+def get_panel_name(
+    obj: click.Command | click.Argument | click.Option, default_name: str
+) -> str:
+    return getattr(obj, _RICH_HELP_PANEL_NAME, None) or default_name