diff --git a/swh/core/db/tests/test_cli.py b/swh/core/db/tests/test_cli.py
--- a/swh/core/db/tests/test_cli.py
+++ b/swh/core/db/tests/test_cli.py
@@ -13,6 +13,7 @@
 from swh.core.cli.db import db as swhdb
 from swh.core.db import BaseDb
 from swh.core.db.pytest_plugin import postgresql_fact
+from swh.core.tests.test_cli import assert_section_contains
 
 
 @pytest.fixture
@@ -20,57 +21,41 @@
     return CliRunner()
 
 
-help_msg = """Usage: swh [OPTIONS] COMMAND [ARGS]...
-
-  Command line interface for Software Heritage.
-
-Options:
-  -l, --log-level [NOTSET|DEBUG|INFO|WARNING|ERROR|CRITICAL]
-                                  Log level (defaults to INFO).
-  --log-config FILENAME           Python yaml logging configuration file.
-  --sentry-dsn TEXT               DSN of the Sentry instance to report to
-  -h, --help                      Show this message and exit.
-
-Notes:
-  If both options are present, --log-level will override the root logger
-  configuration set in --log-config.
-
-  The --log-config YAML must conform to the logging.config.dictConfig schema
-  documented at https://docs.python.org/3/library/logging.config.html.
-
-Commands:
-  db  Software Heritage database generic tools.
-"""
-
-
 def test_cli_swh_help(swhmain, cli_runner):
     swhmain.add_command(swhdb)
     result = cli_runner.invoke(swhmain, ["-h"])
     assert result.exit_code == 0
-    assert result.output == help_msg
-
-
-help_db_msg = """Usage: swh db [OPTIONS] COMMAND [ARGS]...
-
-  Software Heritage database generic tools.
+    assert_section_contains(
+        result.output, "Commands", "db  Software Heritage database generic tools."
+    )
 
-Options:
-  -C, --config-file FILE  Configuration file.
-  -h, --help              Show this message and exit.
 
-Commands:
-  create      Create a database for the Software Heritage <module>.
-  init        Initialize a database for the Software Heritage <module>.
-  init-admin  Execute superuser-level initialization steps (e.g pg
-              extensions,...
-"""
+help_db_snippets = (
+    (
+        "Usage",
+        (
+            "Usage: swh db [OPTIONS] COMMAND [ARGS]...",
+            "Software Heritage database generic tools.",
+        ),
+    ),
+    (
+        "Commands",
+        (
+            "create      Create a database for the Software Heritage <module>.",
+            "init        Initialize a database for the Software Heritage <module>.",
+            "init-admin  Execute superuser-level initialization steps",
+        ),
+    ),
+)
 
 
 def test_cli_swh_db_help(swhmain, cli_runner):
     swhmain.add_command(swhdb)
     result = cli_runner.invoke(swhmain, ["db", "-h"])
     assert result.exit_code == 0
-    assert result.output == help_db_msg
+    for section, snippets in help_db_snippets:
+        for snippet in snippets:
+            assert_section_contains(result.output, section, snippet)
 
 
 @pytest.fixture()
diff --git a/swh/core/tests/test_cli.py b/swh/core/tests/test_cli.py
--- a/swh/core/tests/test_cli.py
+++ b/swh/core/tests/test_cli.py
@@ -5,6 +5,7 @@
 
 import logging
 import textwrap
+from typing import List
 from unittest.mock import patch
 
 import click
@@ -12,35 +13,68 @@
 import pkg_resources
 import pytest
 
-help_msg = """Usage: swh [OPTIONS] COMMAND [ARGS]...
-
-  Command line interface for Software Heritage.
-
-Options:
-  -l, --log-level [NOTSET|DEBUG|INFO|WARNING|ERROR|CRITICAL]
-                                  Log level (defaults to INFO).
-  --log-config FILENAME           Python yaml logging configuration file.
-  --sentry-dsn TEXT               DSN of the Sentry instance to report to
-  -h, --help                      Show this message and exit.
-
-Notes:
-  If both options are present, --log-level will override the root logger
-  configuration set in --log-config.
-
-  The --log-config YAML must conform to the logging.config.dictConfig schema
-  documented at https://docs.python.org/3/library/logging.config.html.
-"""
+help_msg_snippets = (
+    (
+        "Usage",
+        (
+            "swh [OPTIONS] COMMAND [ARGS]...",
+            "Command line interface for Software Heritage.",
+        ),
+    ),
+    ("Options", ("-l, --log-level", "--log-config", "--sentry-dsn", "-h, --help",)),
+)
+
+
+def get_section(cli_output: str, section: str) -> List[str]:
+    """Get the given `section` of the `cli_output`"""
+    result = []
+    in_section = False
+    for line in cli_output.splitlines():
+        if not line:
+            continue
+
+        if in_section:
+            if not line.startswith(" "):
+                break
+        else:
+            if line.startswith(section):
+                in_section = True
+
+        if in_section:
+            result.append(line)
+
+    return result
+
+
+def assert_section_contains(cli_output: str, section: str, snippet: str) -> bool:
+    """Check that a given `section` of the `cli_output` contains the given `snippet`"""
+    section_lines = get_section(cli_output, section)
+    assert section_lines, "Section %s not found in output %r" % (section, cli_output)
+
+    for line in section_lines:
+        if snippet in line:
+            return True
+    else:
+        assert False, "%r not found in section %r of output %r" % (
+            snippet,
+            section,
+            cli_output,
+        )
 
 
 def test_swh_help(swhmain):
     runner = CliRunner()
     result = runner.invoke(swhmain, ["-h"])
     assert result.exit_code == 0
-    assert result.output.startswith(help_msg)
+    for section, snippets in help_msg_snippets:
+        for snippet in snippets:
+            assert_section_contains(result.output, section, snippet)
 
     result = runner.invoke(swhmain, ["--help"])
     assert result.exit_code == 0
-    assert result.output.startswith(help_msg)
+    for section, snippets in help_msg_snippets:
+        for snippet in snippets:
+            assert_section_contains(result.output, section, snippet)
 
 
 def test_command(swhmain):
@@ -67,7 +101,6 @@
     runner = CliRunner()
     result = runner.invoke(swhmain, ["test"])
     assert result.exit_code == 0
-    print(result.output)
     assert result.output.strip() == """Hello SWH!"""