diff --git a/tests/system/framework/hosts/shadow.py b/tests/system/framework/hosts/shadow.py
index 0696ec0de4..ba76ef9676 100644
--- a/tests/system/framework/hosts/shadow.py
+++ b/tests/system/framework/hosts/shadow.py
@@ -398,21 +398,27 @@ def __setitem__(self, key: str, value: str) -> None:
         self.logger.info(f"Setting {key}={value} in {self.path} on {self.host.hostname}")
 
         sep = self.separator
-        grep_match = "=" if sep == "=" else "\\s"
-        awk_match = "=" if sep == "=" else "\\\\s"
+        if sep == "=":
+            grep_pattern = f"^{key}="
+            grep_comment_pattern = f"^# *{key}="
+            awk_pattern = "="
+        else:
+            grep_pattern = f"^{key}\\s+"
+            grep_comment_pattern = f"^# *{key}\\s+"
+            awk_pattern = "[[:space:]]+"
 
         # Escape special characters for awk
         escaped_value = value.replace("/", "\\/")
 
         self.host.conn.run(
             f"""
-            if grep -q '^{key}{grep_match}' {self.path}; then
+            if grep -qE '{grep_pattern}' {self.path}; then
                 awk -v key="{key}" -v val="{escaped_value}" \\
-                    '{{if ($0 ~ "^" key "{awk_match}") print key "{sep}" val; else print $0}}' \\
+                    '{{if ($0 ~ "^" key "{awk_pattern}") print key "{sep}" val; else print $0}}' \\
                     {self.path} > {self.path}.tmp && mv {self.path}.tmp {self.path}
-            elif grep -q '^#\\s*{key}{grep_match}' {self.path}; then
+            elif grep -qE '{grep_comment_pattern}' {self.path}; then
                 awk -v key="{key}" -v val="{escaped_value}" \\
-                    '{{if ($0 ~ "^#\\\\s*" key "{awk_match}") print key "{sep}" val; else print $0}}' \\
+                    '{{if ($0 ~ "^# *" key "{awk_pattern}") print key "{sep}" val; else print $0}}' \\
                     {self.path} > {self.path}.tmp && mv {self.path}.tmp {self.path}
             else
                 echo '{key}{sep}{value}' >> {self.path}
@@ -432,5 +438,8 @@ def __delitem__(self, key: str) -> None:
         self._ensure_exists()
         self.logger.info(f"Removing {key} from {self.path} on {self.host.hostname}")
 
-        match = "=" if self.separator == "=" else "\\s"
-        self.host.conn.run(f"sed -i 's/^{key}{match}.*/#&/' {self.path}", log_level=ProcessLogLevel.Error)
+        if self.separator == "=":
+            pattern = f"^{key}="
+        else:
+            pattern = f"^{key}\\s+"
+        self.host.conn.run(f"sed -iE 's/{pattern}.*/#&/' {self.path}", log_level=ProcessLogLevel.Error)
diff --git a/tests/system/tests/test_groupadd.py b/tests/system/tests/test_groupadd.py
index a9655805d2..fa81d4049f 100644
--- a/tests/system/tests/test_groupadd.py
+++ b/tests/system/tests/test_groupadd.py
@@ -512,3 +512,92 @@ def test_groupadd__invalid_arguments(shadow: Shadow, args: str):
         shadow.groupadd(args)
 
     assert exc_info.value.rc == 2, f"Expected return code 2(invalid usage), got {exc_info.value.rc}"
+
+
+@pytest.mark.topology(KnownTopology.Shadow)
+def test_groupadd__no_gshadow(shadow: Shadow):
+    """
+    :title: Group creation succeeds when /etc/gshadow does not exist
+    :setup:
+        1. Remove /etc/gshadow file
+        2. Set FORCE_SHADOW=no in /etc/login.defs
+    :steps:
+        1. Create group
+        2. Check group entry
+        3. Check that /etc/gshadow file is not present
+    :expectedresults:
+        1. Group is created
+        2. Group entry is found
+        3. /etc/gshadow file is not found
+    :customerscenario: False
+    """
+    shadow.fs.rm("/etc/gshadow")
+
+    shadow.login_defs["FORCE_SHADOW"] = "no"
+
+    shadow.groupadd("tgroup")
+
+    group_entry = shadow.tools.getent.group("tgroup")
+    assert group_entry is not None, "Group should be found"
+    assert group_entry.name == "tgroup", "Incorrect groupname"
+
+    gshadow_file = shadow.fs.exists("/etc/gshadow")
+    assert not gshadow_file, "/etc/gshadow file should not be found"
+
+
+@pytest.mark.topology(KnownTopology.Shadow)
+def test_groupadd__non_unique_requires_gid(shadow: Shadow):
+    """
+    :title: Groupadd command fails when non-unique option is used without GID
+    :setup:
+        1. None required
+    :steps:
+        1. Attempt to create group
+        2. Verify that groupadd command fails
+        3. Check group and gshadow entries
+    :expectedresults:
+        1. Group is not created
+        2. groupadd command fails with error (invalid usage)
+        3. No group or gshadow entries are found
+    :customerscenario: False
+    """
+    with pytest.raises(ProcessError) as exc_info:
+        shadow.groupadd("-o tgroup")
+
+    assert exc_info.value.rc == 2, f"Expected return code 2 (invalid usage), got {exc_info.value.rc}"
+
+    group_entry = shadow.tools.getent.group("tgroup")
+    assert group_entry is None, "Group should not be found"
+
+    if shadow.host.features["gshadow"]:
+        gshadow_entry = shadow.tools.getent.gshadow("tgroup")
+        assert gshadow_entry is None, "Group should not be found"
+
+
+@pytest.mark.topology(KnownTopology.Shadow)
+def test_groupadd__invalid_option(shadow: Shadow):
+    """
+    :title: Group creation fails with invalid option
+    :setup:
+        1. None required
+    :steps:
+        1. Attempt to create group
+        2. Verify that groupadd command fails
+        3. Check group and gshadow entries
+    :expectedresults:
+        1. Group is not created
+        2. groupadd command fails with error (invalid usage)
+        3. No group or gshadow entries are found
+    :customerscenario: False
+    """
+    with pytest.raises(ProcessError) as exc_info:
+        shadow.groupadd("-invalid tgroup")
+
+    assert exc_info.value.rc == 2, f"Expected return code 2 (invalid usage), got {exc_info.value.rc}"
+
+    group_entry = shadow.tools.getent.group("tgroup")
+    assert group_entry is None, "Group should not be found"
+
+    if shadow.host.features["gshadow"]:
+        gshadow_entry = shadow.tools.getent.gshadow("tgroup")
+        assert gshadow_entry is None, "Group should not be found"