diff --git a/configuration.c b/configuration.c
index a055a92413..ac2276083d 100644
--- a/configuration.c
+++ b/configuration.c
@@ -3092,6 +3092,7 @@ static bool config_load_file(global_t *global,
    bool ret                                        = false;
    unsigned tmp_uint                               = 0;
    bool tmp_bool                                   = false;
+   static bool first_load                          = true;
    unsigned msg_color                              = 0;
    char *save                                      = NULL;
    char *override_username                         = NULL;
@@ -3183,13 +3184,24 @@ static bool config_load_file(global_t *global,
                settings->bools.network_remote_enable_user[i], tmp_bool);
    }
 #endif
-   if (config_get_bool(conf, "log_verbosity", &tmp_bool))
+   /* Set verbosity according to config only if the 'v' command line argument was not used
+    * or if it is not the first config load. */
+   if (config_get_bool(conf, "log_verbosity", &tmp_bool) &&
+      (!retroarch_override_setting_is_set(RARCH_OVERRIDE_SETTING_VERBOSITY, NULL) ||
+      !first_load))
    {
       if (tmp_bool)
          verbosity_enable();
       else
          verbosity_disable();
    }
+   /* On first config load, make sure log_to_file is true if 'log-file' command line 
+    * argument was used. */
+   if (retroarch_override_setting_is_set(RARCH_OVERRIDE_SETTING_LOG_TO_FILE, NULL) &&
+      first_load)
+   {
+      configuration_set_bool(settings,settings->bools.log_to_file,true);
+   }
    if (config_get_uint(conf, "frontend_log_level", &tmp_uint))
    {
       verbosity_set_log_level(tmp_uint);
@@ -3620,6 +3632,7 @@ end:
       free(path_settings);
    if (size_settings)
       free(size_settings);
+   first_load = false;
    return ret;
 }
 
@@ -3966,15 +3979,15 @@ success:
  */
 static void config_parse_file(global_t *global)
 {
+   const char *config_path = path_get(RARCH_PATH_CONFIG);
    if (path_is_empty(RARCH_PATH_CONFIG))
    {
       RARCH_LOG("[Config]: Loading default config.\n");
    }
+   else
+       RARCH_LOG("[Config]: Loading config from: \"%s\".\n", config_path);
 
    {
-      const char *config_path = path_get(RARCH_PATH_CONFIG);
-      RARCH_LOG("[Config]: Loading config from: \"%s\".\n", config_path);
-
       if (!config_load_file(global, config_path, config_get_ptr()))
       {
          RARCH_ERR("[Config]: Couldn't find config at path: \"%s\".\n",
diff --git a/retroarch.c b/retroarch.c
index 7ab4d7572b..bb37271452 100644
--- a/retroarch.c
+++ b/retroarch.c
@@ -34647,6 +34647,22 @@ static bool retroarch_parse_input_and_config(
                retroarch_override_setting_set(
                      RARCH_OVERRIDE_SETTING_STATE_PATH, NULL);
                break;
+            case 'v':
+               verbosity_enable();
+               retroarch_override_setting_set(
+                     RARCH_OVERRIDE_SETTING_VERBOSITY, NULL);
+               break;
+            case RA_OPT_LOG_FILE:
+               /* Enable 'log to file' */
+               configuration_set_bool(p_rarch->configuration_settings,
+                     p_rarch->configuration_settings->bools.log_to_file, true);
+
+               retroarch_override_setting_set(
+                     RARCH_OVERRIDE_SETTING_LOG_TO_FILE, NULL);
+
+               /* Cache log file path override */
+               rarch_log_file_set_override(optarg);
+               break;
 
             /* Must handle '?' otherwise you get an infinite loop */
             case '?':
@@ -34657,6 +34673,13 @@ static bool retroarch_parse_input_and_config(
          }
       }
    }
+   verbosity_enabled = verbosity_is_enabled();
+   /* Enable logging to file if verbosity and log-file arguments were passed.
+    * RARCH_OVERRIDE_SETTING_LOG_TO_FILE is set by the RA_OPT_LOG_FILE case above
+    * The parameters passed to rarch_log_file_init are hardcoded as the config
+    * has not yet been initialized at this point. */
+   if (verbosity_enabled && retroarch_override_setting_is_set(RARCH_OVERRIDE_SETTING_LOG_TO_FILE, NULL))
+      rarch_log_file_init(true,false,'\0');
 
    /* Flush out some states that could have been set
     * by core environment variables. */
@@ -34676,6 +34699,15 @@ static bool retroarch_parse_input_and_config(
       config_load(&p_rarch->g_extern);
    }
 
+   verbosity_enabled = verbosity_is_enabled();
+   /* Init logging after config load only if not overridden by command line argument. 
+    * This handles when logging is set in the config but not via the --log-file option. */
+   if (verbosity_enabled && !retroarch_override_setting_is_set(RARCH_OVERRIDE_SETTING_LOG_TO_FILE, NULL))
+      rarch_log_file_init(
+            p_rarch->configuration_settings->bools.log_to_file,
+            p_rarch->configuration_settings->bools.log_to_file_timestamp,
+            p_rarch->configuration_settings->paths.log_dir);
+            
    /* Second pass: All other arguments override the config file */
    optind = 1;
 
@@ -34742,12 +34774,6 @@ static bool retroarch_parse_input_and_config(
                p_rarch->rarch_force_fullscreen = true;
                break;
 
-            case 'v':
-               verbosity_enable();
-               retroarch_override_setting_set(
-                     RARCH_OVERRIDE_SETTING_VERBOSITY, NULL);
-               break;
-
             case 'N':
                {
                   unsigned new_port;
@@ -35052,18 +35078,6 @@ static bool retroarch_parse_input_and_config(
                retroarch_print_version();
                exit(0);
 
-            case RA_OPT_LOG_FILE:
-               /* Enable 'log to file' */
-               configuration_set_bool(p_rarch->configuration_settings,
-                     p_rarch->configuration_settings->bools.log_to_file, true);
-
-               retroarch_override_setting_set(
-                     RARCH_OVERRIDE_SETTING_LOG_TO_FILE, NULL);
-
-               /* Cache log file path override */
-               rarch_log_file_set_override(optarg);
-               break;
-
             case 'h':
 #ifdef HAVE_CONFIGFILE
             case 'c':
@@ -35071,6 +35085,8 @@ static bool retroarch_parse_input_and_config(
 #endif
             case 's':
             case 'S':
+            case 'v':
+            case RA_OPT_LOG_FILE:
                break; /* Handled in the first pass */
 
             case '?':
@@ -35091,14 +35107,6 @@ static bool retroarch_parse_input_and_config(
       }
    }
 
-   verbosity_enabled = verbosity_is_enabled();
-
-   if (verbosity_enabled)
-      rarch_log_file_init(
-            p_rarch->configuration_settings->bools.log_to_file,
-            p_rarch->configuration_settings->bools.log_to_file_timestamp,
-            p_rarch->configuration_settings->paths.log_dir);
-
 #ifdef HAVE_GIT_VERSION
    RARCH_LOG("RetroArch %s (Git %s)\n",
          PACKAGE_VERSION, retroarch_git_version);