diff --git a/agent/nmap_agent.py b/agent/nmap_agent.py
index a23641f3..2ef65eef 100644
--- a/agent/nmap_agent.py
+++ b/agent/nmap_agent.py
@@ -374,16 +374,26 @@ def _emit_fingerprints(
                     raise ValueError(f"Incorrect ip version {version}")
 
                 if host.get("os", {}).get("osmatch") is not None:
-                    os_match_highest = host.get("os").get("osmatch", {})[0]
+                    os_match = host.get("os").get("osmatch")
+                    if len(os_match) > 0:
+                        os_match_highest = os_match[0]
+                    else:
+                        continue
+
+                    if isinstance(os_match_highest, list) and len(os_match_highest) > 0:
+                        os_match_highest = os_match_highest[0]
+                    os_class = os_match_highest.get("osclass", {})
+
+                    if isinstance(os_class, list) and len(os_class) > 0:
+                        os_class = os_class[0]
+                    elif os_class == []:
+                        continue
+
                     fingerprint_data = {
                         "host": host.get("address", {}).get("@addr"),
                         "library_type": "OS",
-                        "library_name": os_match_highest.get("osclass", {}).get(
-                            "@osfamily"
-                        ),
-                        "library_version": os_match_highest.get("osclass").get(
-                            "@osgen"
-                        ),
+                        "library_name": os_class.get("@osfamily"),
+                        "library_version": os_class.get("@osgen"),
                         "detail": os_match_highest.get("@name"),
                     }
                     self.emit(selector, fingerprint_data)
diff --git a/tests/nmap_agent_test.py b/tests/nmap_agent_test.py
index e99add96..413d2476 100644
--- a/tests/nmap_agent_test.py
+++ b/tests/nmap_agent_test.py
@@ -751,7 +751,7 @@ def testAgent_whenHostHaveOs_fingerprintMessageShouldHaveOs(
     agent_persist_mock: Dict[Union[str, bytes], Union[str, bytes]],
     mocker: plugin.MockerFixture,
 ) -> None:
-    """Ensure the agents emits the detected library name with its version."""
+    """Ensure the agent fingerprint OS."""
     del agent_persist_mock
     product_fake_output = {
         "nmaprun": {
@@ -810,3 +810,176 @@ def testAgent_whenHostHaveOs_fingerprintMessageShouldHaveOs(
     assert fingerprint_msg.data["host"] == "127.0.0.1"
     assert fingerprint_msg.data["library_name"] == "Windows"
     assert fingerprint_msg.data["library_version"] == "10"
+
+
+def testAgent_whenOsClassIsList_fingerprintMessageShouldHaveOs(
+    nmap_test_agent: nmap_agent.NmapAgent,
+    agent_mock: List[message.Message],
+    ipv4_msg: message.Message,
+    agent_persist_mock: Dict[Union[str, bytes], Union[str, bytes]],
+    mocker: plugin.MockerFixture,
+) -> None:
+    """Ensure the agent handel osclass when it's a list."""
+    del agent_persist_mock
+    product_fake_output = {
+        "nmaprun": {
+            "host": {
+                "address": {"@addr": "127.0.0.1", "@addrtype": "ipv4"},
+                "ports": {
+                    "port": {
+                        "@portid": "22",
+                        "@protocol": "tcp",
+                        "state": {
+                            "@state": "open",
+                            "@reason": "syn-ack",
+                            "@reason_ttl": "0",
+                        },
+                        "service": {
+                            "@name": "ssh",
+                            "@product": "OpenSSH",
+                            "@version": "7.4",
+                            "cpe": "cpe:/a:openbsd:openssh:7.4",
+                        },
+                    }
+                },
+                "os": {
+                    "osmatch": [
+                        [
+                            {
+                                "@name": "Microsoft Windows 10 1511",
+                                "@accuracy": "88",
+                                "@line": "69505",
+                                "osclass": [
+                                    {
+                                        "@type": "specialized",
+                                        "@vendor": "Microsoft",
+                                        "@osfamily": "Windows",
+                                        "@osgen": "10",
+                                        "@accuracy": "88",
+                                        "cpe": "cpe:/o:microsoft:windows_10:1511",
+                                    }
+                                ],
+                            }
+                        ]
+                    ]
+                },
+            }
+        }
+    }
+
+    mocker.patch(
+        "agent.nmap_wrapper.NmapWrapper.scan_hosts",
+        return_value=(product_fake_output, ""),
+    )
+
+    nmap_test_agent.process(ipv4_msg)
+
+    assert len(agent_mock) == 4
+    assert agent_mock[0].selector == "v3.asset.ip.v4.port.service"
+    assert agent_mock[1].selector == "v3.report.vulnerability"
+    fingerprint_msg = agent_mock[2]
+    assert fingerprint_msg.selector == "v3.fingerprint.ip.v4.service.library"
+    assert fingerprint_msg.data["host"] == "127.0.0.1"
+    assert fingerprint_msg.data["library_name"] == "Windows"
+    assert fingerprint_msg.data["library_version"] == "10"
+
+
+def testAgent_whenOsMatchIsEmptyList_fingerprintMessageShouldHaveOs(
+    nmap_test_agent: nmap_agent.NmapAgent,
+    agent_mock: List[message.Message],
+    ipv4_msg: message.Message,
+    agent_persist_mock: Dict[Union[str, bytes], Union[str, bytes]],
+    mocker: plugin.MockerFixture,
+) -> None:
+    """Ensure the agent handel osmatch when it's an empty list."""
+    del agent_persist_mock
+    product_fake_output = {
+        "nmaprun": {
+            "host": {
+                "address": {"@addr": "127.0.0.1", "@addrtype": "ipv4"},
+                "ports": {
+                    "port": {
+                        "@portid": "22",
+                        "@protocol": "tcp",
+                        "state": {
+                            "@state": "open",
+                            "@reason": "syn-ack",
+                            "@reason_ttl": "0",
+                        },
+                        "service": {
+                            "@name": "ssh",
+                            "@product": "OpenSSH",
+                            "@version": "7.4",
+                            "cpe": "cpe:/a:openbsd:openssh:7.4",
+                        },
+                    }
+                },
+                "os": {"osmatch": []},
+            }
+        }
+    }
+
+    mocker.patch(
+        "agent.nmap_wrapper.NmapWrapper.scan_hosts",
+        return_value=(product_fake_output, ""),
+    )
+
+    nmap_test_agent.process(ipv4_msg)
+
+    assert len(agent_mock) == 2
+
+
+def testAgent_whenOsMatchIsList_fingerprintMessageShouldHaveOs(
+    nmap_test_agent: nmap_agent.NmapAgent,
+    agent_mock: List[message.Message],
+    ipv4_msg: message.Message,
+    agent_persist_mock: Dict[Union[str, bytes], Union[str, bytes]],
+    mocker: plugin.MockerFixture,
+) -> None:
+    """Ensure the agent handel osmatch when it's a list."""
+    del agent_persist_mock
+    product_fake_output = {
+        "nmaprun": {
+            "host": {
+                "address": {"@addr": "127.0.0.1", "@addrtype": "ipv4"},
+                "ports": {
+                    "port": {
+                        "@portid": "22",
+                        "@protocol": "tcp",
+                        "state": {
+                            "@state": "open",
+                            "@reason": "syn-ack",
+                            "@reason_ttl": "0",
+                        },
+                        "service": {
+                            "@name": "ssh",
+                            "@product": "OpenSSH",
+                            "@version": "7.4",
+                            "cpe": "cpe:/a:openbsd:openssh:7.4",
+                        },
+                    }
+                },
+                "os": {
+                    "osmatch": [
+                        [
+                            {
+                                "@name": "Microsoft Windows 10 1511",
+                                "@accuracy": "88",
+                                "@line": "69505",
+                                "osclass": [],
+                            }
+                        ]
+                    ]
+                },
+            }
+        }
+    }
+
+    mocker.patch(
+        "agent.nmap_wrapper.NmapWrapper.scan_hosts",
+        return_value=(product_fake_output, ""),
+    )
+
+    nmap_test_agent.process(ipv4_msg)
+
+    assert len(agent_mock) == 2