diff --git a/userspace/falco/configuration.cpp b/userspace/falco/configuration.cpp
index 0b906e2a..27f439cb 100644
--- a/userspace/falco/configuration.cpp
+++ b/userspace/falco/configuration.cpp
@@ -133,12 +133,20 @@ config_loaded_res falco_configuration::init_from_file(
 		std::cerr << "Cannot read config file (" + conf_filename + "): " + e.what() + "\n";
 		throw e;
 	}
-	init_cmdline_options(cmdline_options);
 
 	// Only report top most schema validation status
 	res[conf_filename] = validation_status[0];
 
+	// Load any `-o config_files=foo.yaml` cmdline additional option
+	load_cmdline_config_files(cmdline_options);
+
+	// Merge all config files (both from main falco.yaml and `-o config_files=foo.yaml`)
 	merge_config_files(conf_filename, res);
+
+	// Load all other `-o` cmdline options to override any config key
+	init_cmdline_options(cmdline_options);
+
+	// Finally load the parsed config to our structure
 	load_yaml(conf_filename);
 
 	return res;
@@ -766,6 +774,16 @@ static bool split(const std::string &str, char delim, std::pair<std::string, std
 	return true;
 }
 
+void falco_configuration::load_cmdline_config_files(
+        const std::vector<std::string> &cmdline_options) {
+	for(const std::string &option : cmdline_options) {
+		// Set all config_files options
+		if(option.rfind(yaml_helper::configs_key, 0) == 0) {
+			set_cmdline_option(option);
+		}
+	}
+}
+
 void falco_configuration::init_cmdline_options(const std::vector<std::string> &cmdline_options) {
 	for(const std::string &option : cmdline_options) {
 		set_cmdline_option(option);
diff --git a/userspace/falco/configuration.h b/userspace/falco/configuration.h
index c92ada52..6110352a 100644
--- a/userspace/falco/configuration.h
+++ b/userspace/falco/configuration.h
@@ -221,6 +221,8 @@ private:
 	void init_logger();
 	void load_engine_config(const std::string& config_name);
 	void init_cmdline_options(const std::vector<std::string>& cmdline_options);
+	void load_cmdline_config_files(const std::vector<std::string>& cmdline_options);
+
 	/**
 	 * Given a <key>=<value> specifier, set the appropriate option
 	 * in the underlying yaml config. <key> can contain '.'