diff --git a/config.def.h b/config.def.h
index a2f36dab486..bdb680d1aba 100644
--- a/config.def.h
+++ b/config.def.h
@@ -1124,6 +1124,10 @@
  * input remap file */
 #define DEFAULT_NOTIFICATION_SHOW_REMAP_LOAD true
 
+/* Display a notification when a user is mapped to a core
+ * port on first button press */
+#define DEFAULT_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT true
+
 /* Display a notification when loading a
  * configuration override file */
 #define DEFAULT_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD true
@@ -1620,6 +1624,10 @@
  * gamepads, plug-and-play style. */
 #define DEFAULT_INPUT_AUTODETECT_ENABLE true
 
+/* Map user to core port on first button press. First person
+ * to press a button is player 1, second is player 2, etc. */
+#define DEFAULT_INPUT_REMAP_PORTS_ON_BUTTON_PRESS false
+
 /* Enables accelerometer/gyroscope/illuminance
  * sensor input, if supported */
 #if defined(ANDROID)
diff --git a/configuration.c b/configuration.c
index ad7e0db6784..9b8f1ebe356 100644
--- a/configuration.c
+++ b/configuration.c
@@ -1934,6 +1934,7 @@ static struct config_bool_setting *populate_settings_bool(
    SETTING_BOOL("notification_show_cheats_applied", &settings->bools.notification_show_cheats_applied, true, DEFAULT_NOTIFICATION_SHOW_CHEATS_APPLIED, false);
    SETTING_BOOL("notification_show_patch_applied", &settings->bools.notification_show_patch_applied, true, DEFAULT_NOTIFICATION_SHOW_PATCH_APPLIED, false);
    SETTING_BOOL("notification_show_remap_load",  &settings->bools.notification_show_remap_load, true, DEFAULT_NOTIFICATION_SHOW_REMAP_LOAD, false);
+   SETTING_BOOL("notification_show_user_mapped_to_core_port",  &settings->bools.notification_show_user_mapped_to_core_port, true, DEFAULT_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT, false);
    SETTING_BOOL("notification_show_config_override_load", &settings->bools.notification_show_config_override_load, true, DEFAULT_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD, false);
    SETTING_BOOL("notification_show_set_initial_disk", &settings->bools.notification_show_set_initial_disk, true, DEFAULT_NOTIFICATION_SHOW_SET_INITIAL_DISK, false);
    SETTING_BOOL("notification_show_disk_control", &settings->bools.notification_show_disk_control, true, DEFAULT_NOTIFICATION_SHOW_DISK_CONTROL, false);
@@ -2177,6 +2178,7 @@ static struct config_bool_setting *populate_settings_bool(
    SETTING_BOOL("input_turbo_allow_dpad",        &settings->bools.input_turbo_allow_dpad, true, DEFAULT_TURBO_ALLOW_DPAD, false);
    SETTING_BOOL("input_auto_mouse_grab",         &settings->bools.input_auto_mouse_grab, true, DEFAULT_INPUT_AUTO_MOUSE_GRAB, false);
    SETTING_BOOL("input_remap_binds_enable",      &settings->bools.input_remap_binds_enable, true, true, false);
+   SETTING_BOOL("input_remap_ports_on_button_press",   &settings->bools.input_remap_ports_on_button_press, true, DEFAULT_INPUT_REMAP_PORTS_ON_BUTTON_PRESS, false);
    SETTING_BOOL("input_remap_sort_by_controller_enable",      &settings->bools.input_remap_sort_by_controller_enable, true, false, false);
    SETTING_BOOL("input_hotkey_device_merge",     &settings->bools.input_hotkey_device_merge, true, DEFAULT_INPUT_HOTKEY_DEVICE_MERGE, false);
    SETTING_BOOL("input_hotkey_follows_player1",  &settings->bools.input_hotkey_follows_player1, true, DEFAULT_INPUT_HOTKEY_FOLLOWS_PLAYER1, false);
diff --git a/configuration.h b/configuration.h
index 57e8f129050..79b38afdd07 100644
--- a/configuration.h
+++ b/configuration.h
@@ -702,6 +702,7 @@ typedef struct settings
       /* Input */
       bool input_remap_binds_enable;
       bool input_remap_sort_by_controller_enable;
+      bool input_remap_ports_on_button_press;
       bool input_autodetect_enable;
       bool input_sensors_enable;
       bool input_overlay_enable;
@@ -758,6 +759,7 @@ typedef struct settings
       bool notification_show_cheats_applied;
       bool notification_show_patch_applied;
       bool notification_show_remap_load;
+      bool notification_show_user_mapped_to_core_port;
       bool notification_show_config_override_load;
       bool notification_show_set_initial_disk;
       bool notification_show_disk_control;
diff --git a/input/input_driver.c b/input/input_driver.c
index beba85e1b20..155211ca348 100644
--- a/input/input_driver.c
+++ b/input/input_driver.c
@@ -6013,6 +6013,103 @@ static void input_keys_pressed(
       input_st->input_hotkey_block_counter = 0;
 }
 
+/* Ignore d-pad buttons to avoid false positives.
+ * Some wireless gamepad receivers report 0 values for all axes when the
+ * gamepad is powered off or not yet connected. Since 0 represents the
+ * "left" and "up" positions for d-pad axes, this creates false button
+ * presses that could trigger unwanted input mapping.
+ */
+static bool any_button_ex_dpad_pressed(int32_t state)
+{
+   static const uint32_t button_mask =
+      (1 << RETRO_DEVICE_ID_JOYPAD_A)     |
+      (1 << RETRO_DEVICE_ID_JOYPAD_B)     |
+      (1 << RETRO_DEVICE_ID_JOYPAD_X)     |
+      (1 << RETRO_DEVICE_ID_JOYPAD_Y)     |
+      (1 << RETRO_DEVICE_ID_JOYPAD_L)     |
+      (1 << RETRO_DEVICE_ID_JOYPAD_R)     |
+      (1 << RETRO_DEVICE_ID_JOYPAD_L2)    |
+      (1 << RETRO_DEVICE_ID_JOYPAD_R2)    |
+      (1 << RETRO_DEVICE_ID_JOYPAD_L3)    |
+      (1 << RETRO_DEVICE_ID_JOYPAD_R3)    |
+      (1 << RETRO_DEVICE_ID_JOYPAD_START) |
+      (1 << RETRO_DEVICE_ID_JOYPAD_SELECT);
+
+   return (state & button_mask) != 0;
+}
+
+/* Returns MAX_USERS if all core ports are mapped to a user. */
+static unsigned get_first_free_core_port(settings_t *settings)
+{
+   unsigned core_port_idx;
+   for (core_port_idx = 0; core_port_idx < MAX_USERS; core_port_idx++)
+   {
+      unsigned *core_port_users = settings->uints.input_remap_port_map[core_port_idx];
+      if (core_port_users[0] == MAX_USERS)
+         return core_port_idx;
+   }
+
+   return MAX_USERS;
+}
+
+static void map_user_to_first_free_core_port(unsigned user_idx, settings_t *settings)
+{
+   unsigned core_port_idx;
+
+   if (!settings || user_idx >= MAX_USERS)
+   {
+      RARCH_ERR("[Automap] Invalid parameters\n");
+      return;
+   }
+
+   /* Check if user is already mapped */
+   if (settings->uints.input_remap_ports[user_idx] < MAX_USERS)
+   {
+      RARCH_LOG("[Automap] User %u already mapped to core port %u\n", 
+            user_idx, settings->uints.input_remap_ports[user_idx]);
+      return;
+   }
+
+   core_port_idx = get_first_free_core_port(settings);
+
+   if (core_port_idx < MAX_USERS)
+   {
+      configuration_set_uint(settings,
+            settings->uints.input_remap_ports[user_idx], core_port_idx);
+      configuration_set_uint(settings,
+            settings->uints.input_libretro_device[core_port_idx], RETRO_DEVICE_JOYPAD);
+
+      input_remapping_update_port_map();
+
+      RARCH_LOG("[Automap] user %u mapped to core port %u\n", user_idx, core_port_idx);
+
+      if (settings->bools.notification_show_user_mapped_to_core_port)
+      {
+         unsigned joypad_idx = settings->uints.input_joypad_index[user_idx];
+         const char *device_display_name = input_config_get_device_display_name(joypad_idx);
+         char msg[128] = { '\0'};
+
+         if (string_is_empty(device_display_name))
+            snprintf(msg, sizeof(msg),
+                  msg_hash_to_str(MSG_PORT_MAPPED_TO_CORE_PORT_NR),
+                  user_idx + 1,
+                  core_port_idx + 1);
+         else
+            snprintf(msg, sizeof(msg),
+                  msg_hash_to_str(MSG_DEVICE_MAPPED_TO_CORE_PORT_NR),
+                  device_display_name,
+                  core_port_idx + 1);
+
+         runloop_msg_queue_push(msg, strlen(msg), 1, 180, true, NULL,
+               MESSAGE_QUEUE_ICON_DEFAULT, MESSAGE_QUEUE_CATEGORY_INFO);
+      }
+   }
+   else
+   {
+      RARCH_LOG("[Automap] No free core ports - user %u not mapped\n", user_idx);
+   }
+}
+
 void input_driver_poll(void)
 {
    size_t i, j;
@@ -6029,9 +6126,27 @@ void input_driver_poll(void)
       *sec_joypad                 = NULL;
 #endif
    bool input_remap_binds_enable  = settings->bools.input_remap_binds_enable;
+   bool input_remap_ports_on_button_press
+                                  = settings->bools.input_remap_ports_on_button_press;
    float input_axis_threshold     = settings->floats.input_axis_threshold;
    uint8_t max_users              = (uint8_t)settings->uints.input_max_users;
 
+   /* This rarch_joypad_info_t struct contains the device index + autoconfig binds for the
+    * controller to be queried, and also (for unknown reasons) the analog axis threshold
+    * when mapping analog stick to dpad input. */
+   for (i = 0; i < max_users; i++)
+   {
+      joypad_info[i].axis_threshold = input_axis_threshold;
+      joypad_info[i].joy_idx        = settings->uints.input_joypad_index[i];
+      joypad_info[i].auto_binds     = input_autoconf_binds[joypad_info[i].joy_idx];
+   }
+
+#ifdef HAVE_MENU
+   input_remap_ports_on_button_press =
+            input_remap_ports_on_button_press
+         && !(menu_state_get_ptr()->flags & MENU_ST_FLAG_ALIVE);
+#endif
+
    if (joypad && joypad->poll)
       joypad->poll();
    if (sec_joypad && sec_joypad->poll)
@@ -6040,22 +6155,49 @@ void input_driver_poll(void)
          && input_st->current_driver->poll)
       input_st->current_driver->poll(input_st->current_data);
 
+   if (input_remap_ports_on_button_press)
+   {
+      for (i = 0; i < max_users; i++)
+      {
+         bool user_already_mapped = settings->uints.input_remap_ports[i] < MAX_USERS;
+
+         if (!user_already_mapped)
+         {
+            int32_t buttons_st = input_state_wrap(input_st->current_driver, input_st->current_data,
+                  joypad, sec_joypad, &joypad_info[i],
+                  (*input_st->libretro_input_binds),
+                  (input_st->flags & INP_FLAG_KB_MAPPING_BLOCKED) ? true : false,
+                  (unsigned)i,
+                  RETRO_DEVICE_JOYPAD, 0, RETRO_DEVICE_ID_JOYPAD_MASK);
+
+            if (any_button_ex_dpad_pressed(buttons_st))
+               map_user_to_first_free_core_port(i, settings);
+         }
+      }
+   }
+
 #ifdef HAVE_OVERLAY
    if (      input_st->overlay_ptr
          && (input_st->overlay_ptr->flags & INPUT_OVERLAY_ALIVE))
    {
       unsigned input_analog_dpad_mode = settings->uints.input_analog_dpad_mode[0];
+      unsigned mapped_port            = settings->uints.input_remap_ports[0];
+      bool first_user_is_mapped       = mapped_port < MAX_USERS;
       float input_overlay_opacity     = (input_st->overlay_ptr->flags & INPUT_OVERLAY_IS_OSK)
          ? settings->floats.input_osk_overlay_opacity
          : settings->floats.input_overlay_opacity;
 
+      /* If user 0 is not mapped yet, use the port they would be mapped
+       * to on overlay button press to get the input_analog_dpad_mode. */
+      if (!first_user_is_mapped && input_remap_ports_on_button_press)
+         mapped_port = get_first_free_core_port(settings);
+
       switch (input_analog_dpad_mode)
       {
          case ANALOG_DPAD_LSTICK:
          case ANALOG_DPAD_RSTICK:
             {
-               unsigned mapped_port      = settings->uints.input_remap_ports[0];
-               if (input_st->analog_requested[mapped_port])
+               if ((mapped_port < MAX_USERS) && input_st->analog_requested[mapped_port])
                   input_analog_dpad_mode = ANALOG_DPAD_NONE;
             }
             break;
@@ -6077,6 +6219,12 @@ void input_driver_poll(void)
             input_overlay_opacity,
             input_analog_dpad_mode,
             settings->floats.input_axis_threshold);
+
+      if (!first_user_is_mapped && input_remap_ports_on_button_press)
+      {
+         if (input_st->overlay_ptr->overlay_state.buttons.data[0])
+            map_user_to_first_free_core_port(0, settings);
+      }
    }
 #endif
 
@@ -6089,9 +6237,6 @@ void input_driver_poll(void)
       return;
    }
 
-   /* This rarch_joypad_info_t struct contains the device index + autoconfig binds for the
-    * controller to be queried, and also (for unknown reasons) the analog axis threshold
-    * when mapping analog stick to dpad input. */
    for (i = 0; i < max_users; i++)
    {
       uint16_t button_id = RARCH_TURBO_ENABLE;
@@ -6100,10 +6245,6 @@ void input_driver_poll(void)
       if (settings->ints.input_turbo_bind != -1)
          button_id = settings->ints.input_turbo_bind;
 
-      joypad_info[i].axis_threshold        = input_axis_threshold;
-      joypad_info[i].joy_idx               = settings->uints.input_joypad_index[i];
-      joypad_info[i].auto_binds            = input_autoconf_binds[joypad_info[i].joy_idx];
-
       input_st->turbo_btns.frame_enable[i] =
                (*input_st->libretro_input_binds[i])[button_id].valid
             && turbo_enable ?
@@ -6142,8 +6283,10 @@ void input_driver_poll(void)
       {
          input_bits_t current_inputs;
          unsigned mapped_port            = settings->uints.input_remap_ports[i];
-         unsigned device                 = settings->uints.input_libretro_device[mapped_port]
-                                           & RETRO_DEVICE_MASK;
+         unsigned device                 = ((mapped_port < MAX_USERS)
+                                               ? settings->uints.input_libretro_device[mapped_port]
+                                               : RETRO_DEVICE_NONE
+                                           ) & RETRO_DEVICE_MASK;
          input_bits_t *p_new_state       = (input_bits_t*)&current_inputs;
          unsigned input_analog_dpad_mode = settings->uints.input_analog_dpad_mode[i];
 
@@ -6151,7 +6294,7 @@ void input_driver_poll(void)
          {
             case ANALOG_DPAD_LSTICK:
             case ANALOG_DPAD_RSTICK:
-               if (input_st->analog_requested[mapped_port])
+               if ((mapped_port < MAX_USERS) && input_st->analog_requested[mapped_port])
                   input_analog_dpad_mode = ANALOG_DPAD_NONE;
                break;
             case ANALOG_DPAD_LSTICK_FORCED:
@@ -6705,6 +6848,11 @@ void input_remapping_update_port_map(void)
          port_map_index[remap_port]++;
       }
    }
+
+   /* Changing mapped port may leave a core port unused;
+    * reinitialise controllers to ensure that any such
+    * ports are set to 'RETRO_DEVICE_NONE' */
+   command_event(CMD_EVENT_CONTROLLER_INIT, NULL);
 }
 
 void input_remapping_deinit(bool save_remap)
@@ -6723,6 +6871,29 @@ void input_remapping_deinit(bool save_remap)
                                |    RUNLOOP_FLAG_REMAPS_GAME_ACTIVE);
 }
 
+void input_remapping_set_remap_ports_defaults(void)
+{
+   unsigned i;
+   settings_t *settings = config_get_ptr();
+   bool remap_on_button_press = settings->bools.input_remap_ports_on_button_press;
+
+   for (i = 0; i < MAX_USERS; i++)
+   {
+      configuration_set_uint(settings,
+         settings->uints.input_remap_ports[i],
+         remap_on_button_press ? MAX_USERS : i);
+
+      configuration_set_uint(settings,
+         settings->uints.input_libretro_device[i],
+         remap_on_button_press ? RETRO_DEVICE_NONE : RETRO_DEVICE_JOYPAD);
+   }
+
+   /* Need to call 'input_remapping_update_port_map()'
+    * whenever 'settings->uints.input_remap_ports'
+    * is modified */
+   input_remapping_update_port_map();
+}
+
 void input_remapping_set_defaults(bool clear_cache)
 {
    unsigned i, j;
@@ -6747,16 +6918,9 @@ void input_remapping_set_defaults(bool clear_cache)
       for (j = RARCH_FIRST_CUSTOM_BIND; j < (RARCH_FIRST_CUSTOM_BIND + 8); j++)
          configuration_set_uint(settings,
                settings->uints.input_remap_ids[i][j], j);
-
-      /* Controller port remaps */
-      configuration_set_uint(settings,
-            settings->uints.input_remap_ports[i], i);
    }
 
-   /* Need to call 'input_remapping_update_port_map()'
-    * whenever 'settings->uints.input_remap_ports'
-    * is modified */
-   input_remapping_update_port_map();
+   input_remapping_set_remap_ports_defaults();
 
    /* Restore 'global' settings that were cached on
     * the last core init
diff --git a/input/input_remapping.h b/input/input_remapping.h
index 064770448fe..896a1ed6270 100644
--- a/input/input_remapping.h
+++ b/input/input_remapping.h
@@ -92,6 +92,30 @@ void input_remapping_deinit(bool save_remap);
  */
 void input_remapping_set_defaults(bool clear_cache);
 
+/**
+ * Used to set the default port mapping values within the `settings` struct.
+ * Only sets port mapping related values, not button/keyboard/analog remaps.
+ *
+ * If settings->bools.input_remap_ports_on_button_press is true, leave all
+ * users/devices disconnected. Users will be mapped to a core port on first
+ * button press.
+ *
+ * user 0 -> core port MAX_USERS (RETRO_DEVICE_NONE)
+ * user 1 -> core port MAX_USERS (RETRO_DEVICE_NONE)
+ * ...
+ * user n -> core port MAX_USERS (RETRO_DEVICE_NONE)
+ *
+ * Else map each user to a core port and set all devices to RETRO_DEVICE_JOYPAD:
+ *
+ * user 0 -> core port 0 (RETRO_DEVICE_JOYPAD)
+ * user 1 -> core port 1 (RETRO_DEVICE_JOYPAD)
+ * ...
+ * user n -> core port n (RETRO_DEVICE_JOYPAD)
+ *
+ * (where n = MAX_USERS - 1)
+ */
+void input_remapping_set_remap_ports_defaults(void);
+
 /**
  * Checks `input_config_bind_map` for the requested `input_bind_map`, and if
  * the bind has been registered, returns its base.
diff --git a/intl/msg_hash_lbl.h b/intl/msg_hash_lbl.h
index 514bbe2c4a1..3df3004d4e7 100644
--- a/intl/msg_hash_lbl.h
+++ b/intl/msg_hash_lbl.h
@@ -2170,6 +2170,10 @@ MSG_HASH(
    MENU_ENUM_LABEL_INPUT_REMAP_BINDS_ENABLE,
    "input_remap_binds_enable"
    )
+MSG_HASH(
+   MENU_ENUM_LABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,
+   "input_remap_ports_on_button_press"
+   )
 MSG_HASH(
    MENU_ENUM_LABEL_INPUT_REMAP_SORT_BY_CONTROLLER_ENABLE,
    "input_remap_sort_by_controller_enable"
@@ -6266,6 +6270,10 @@ MSG_HASH(
    MENU_ENUM_LABEL_NOTIFICATION_SHOW_REMAP_LOAD,
    "notification_show_remap_load"
    )
+MSG_HASH(
+   MENU_ENUM_LABEL_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT,
+   "notification_show_user_mapped_to_core_port"
+   )
 MSG_HASH(
    MENU_ENUM_LABEL_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD,
    "notification_show_config_override_load"
diff --git a/intl/msg_hash_us.h b/intl/msg_hash_us.h
index 2c72e41a950..70ad32fa7fd 100644
--- a/intl/msg_hash_us.h
+++ b/intl/msg_hash_us.h
@@ -3337,6 +3337,14 @@ MSG_HASH(
    MENU_ENUM_SUBLABEL_INPUT_REMAP_BINDS_ENABLE,
    "Override the input binds with the remapped binds set for the current core."
    )
+MSG_HASH(
+   MENU_ENUM_LABEL_VALUE_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,
+   "Remap Ports on Button Press"
+   )
+MSG_HASH(
+   MENU_ENUM_SUBLABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,
+   "First user to press a button becomes player 1, second becomes player 2, etc."
+   )
 MSG_HASH(
    MENU_ENUM_LABEL_VALUE_INPUT_REMAP_SORT_BY_CONTROLLER_ENABLE,
    "Sort Remaps By Gamepad"
@@ -6001,6 +6009,14 @@ MSG_HASH(
    MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_REMAP_LOAD,
    "Display an on-screen message when loading input remap files."
    )
+MSG_HASH(
+   MENU_ENUM_LABEL_VALUE_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT,
+   "Remap Ports on Button Press Notifications"
+   )
+MSG_HASH(
+   MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT,
+   "Display an on-screen message when a user is mapped to a core port."
+   )
 MSG_HASH(
    MENU_ENUM_LABEL_VALUE_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD,
    "Config Override Loaded Notifications"
@@ -15554,6 +15570,14 @@ MSG_HASH(
    MSG_DEVICE_NOT_CONFIGURED_FALLBACK_NR,
    "%s (%u/%u) not configured, using fallback"
    )
+MSG_HASH(
+   MSG_DEVICE_MAPPED_TO_CORE_PORT_NR,
+   "%s is Player %u"
+   )
+MSG_HASH(
+   MSG_PORT_MAPPED_TO_CORE_PORT_NR,
+   "Port %u is Player %u"
+   )
 MSG_HASH(
    MSG_BLUETOOTH_SCAN_COMPLETE,
    "Bluetooth scan complete."
diff --git a/menu/cbs/menu_cbs_sublabel.c b/menu/cbs/menu_cbs_sublabel.c
index 07a3962e76d..dadd22d7517 100644
--- a/menu/cbs/menu_cbs_sublabel.c
+++ b/menu/cbs/menu_cbs_sublabel.c
@@ -688,6 +688,7 @@ DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_cheats_applied,  M
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_patch_applied,   MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_PATCH_APPLIED)
 #endif
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_remap_load,  MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_REMAP_LOAD)
+DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_user_mapped_to_core_port, MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_config_override_load, MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_set_initial_disk, MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_SET_INITIAL_DISK)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_notification_show_disk_control, MENU_ENUM_SUBLABEL_NOTIFICATION_SHOW_DISK_CONTROL)
@@ -824,6 +825,7 @@ DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_replay_max_keep,               MENU_
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_replay_checkpoint_interval,    MENU_ENUM_SUBLABEL_REPLAY_CHECKPOINT_INTERVAL)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_replay_checkpoint_deserialize, MENU_ENUM_SUBLABEL_REPLAY_CHECKPOINT_DESERIALIZE)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_input_remap_binds_enable,      MENU_ENUM_SUBLABEL_INPUT_REMAP_BINDS_ENABLE)
+DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_input_remap_ports_on_button_press, MENU_ENUM_SUBLABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_input_remap_sort_by_controller_enable,      MENU_ENUM_SUBLABEL_INPUT_REMAP_SORT_BY_CONTROLLER_ENABLE)
 DEFAULT_SUBLABEL_MACRO(action_bind_sublabel_input_autodetect_enable,       MENU_ENUM_SUBLABEL_INPUT_AUTODETECT_ENABLE)
 #if defined(HAVE_DINPUT) || defined(HAVE_WINRAWINPUT)
@@ -4147,6 +4149,9 @@ int menu_cbs_init_bind_sublabel(menu_file_list_cbs_t *cbs,
          case MENU_ENUM_LABEL_INPUT_REMAP_BINDS_ENABLE:
             BIND_ACTION_SUBLABEL(cbs, action_bind_sublabel_input_remap_binds_enable);
             break;
+         case MENU_ENUM_LABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS:
+            BIND_ACTION_SUBLABEL(cbs, action_bind_sublabel_input_remap_ports_on_button_press);
+            break;
          case MENU_ENUM_LABEL_INPUT_REMAP_SORT_BY_CONTROLLER_ENABLE:
             BIND_ACTION_SUBLABEL(cbs, action_bind_sublabel_input_remap_sort_by_controller_enable);
             break;
@@ -4535,6 +4540,9 @@ int menu_cbs_init_bind_sublabel(menu_file_list_cbs_t *cbs,
          case MENU_ENUM_LABEL_NOTIFICATION_SHOW_REMAP_LOAD:
             BIND_ACTION_SUBLABEL(cbs, action_bind_sublabel_notification_show_remap_load);
             break;
+         case MENU_ENUM_LABEL_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT:
+            BIND_ACTION_SUBLABEL(cbs, action_bind_sublabel_notification_show_user_mapped_to_core_port);
+            break;
          case MENU_ENUM_LABEL_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD:
             BIND_ACTION_SUBLABEL(cbs, action_bind_sublabel_notification_show_config_override_load);
             break;
diff --git a/menu/menu_displaylist.c b/menu/menu_displaylist.c
index 8b3de10cbd2..2a875a88631 100644
--- a/menu/menu_displaylist.c
+++ b/menu/menu_displaylist.c
@@ -8278,6 +8278,7 @@ unsigned menu_displaylist_build_list(
                {MENU_ENUM_LABEL_INPUT_BIND_HOLD,                       PARSE_ONLY_UINT,  true},
                {MENU_ENUM_LABEL_INPUT_AUTODETECT_ENABLE,               PARSE_ONLY_BOOL,  true},
                {MENU_ENUM_LABEL_INPUT_REMAP_BINDS_ENABLE,              PARSE_ONLY_BOOL,  true},
+               {MENU_ENUM_LABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,     PARSE_ONLY_BOOL,  true},
                {MENU_ENUM_LABEL_INPUT_REMAP_SORT_BY_CONTROLLER_ENABLE, PARSE_ONLY_BOOL,  true},
                {MENU_ENUM_LABEL_INPUT_ICADE_ENABLE,                    PARSE_ONLY_BOOL,  true},
                {MENU_ENUM_LABEL_INPUT_SMALL_KEYBOARD_ENABLE,           PARSE_ONLY_BOOL,  true},
@@ -10853,6 +10854,7 @@ unsigned menu_displaylist_build_list(
                {MENU_ENUM_LABEL_NOTIFICATION_SHOW_PATCH_APPLIED,         PARSE_ONLY_BOOL,  false },
 #endif
                {MENU_ENUM_LABEL_NOTIFICATION_SHOW_REMAP_LOAD,            PARSE_ONLY_BOOL,  false },
+               {MENU_ENUM_LABEL_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT, PARSE_ONLY_BOOL,  false },
                {MENU_ENUM_LABEL_NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD,  PARSE_ONLY_BOOL,  false },
                {MENU_ENUM_LABEL_NOTIFICATION_SHOW_SET_INITIAL_DISK,      PARSE_ONLY_BOOL,  false },
                {MENU_ENUM_LABEL_NOTIFICATION_SHOW_DISK_CONTROL,          PARSE_ONLY_BOOL,  false },
@@ -12464,8 +12466,10 @@ bool menu_displaylist_ctl(enum menu_displaylist_ctl_state type,
 
                {
                   unsigned j;
-                  unsigned device  = settings->uints.input_libretro_device[mapped_port];
-                  device          &= RETRO_DEVICE_MASK;
+                  unsigned device = ((mapped_port < MAX_USERS)
+                                        ? settings->uints.input_libretro_device[mapped_port]
+                                        : RETRO_DEVICE_NONE
+                                    ) & RETRO_DEVICE_MASK;
 
                   if (device == RETRO_DEVICE_JOYPAD || device == RETRO_DEVICE_ANALOG)
                   {
diff --git a/menu/menu_setting.c b/menu/menu_setting.c
index 207bd6cc524..0bc52f1538c 100644
--- a/menu/menu_setting.c
+++ b/menu/menu_setting.c
@@ -5566,17 +5566,12 @@ static int setting_action_left_input_remap_port(
    if (settings->uints.input_remap_ports[port] > 0)
       settings->uints.input_remap_ports[port]--;
    else
-      settings->uints.input_remap_ports[port] = MAX_USERS - 1;
+      settings->uints.input_remap_ports[port] = MAX_USERS;
 
    /* Must be called whenever settings->uints.input_remap_ports
     * is modified */
    input_remapping_update_port_map();
 
-   /* Changing mapped port may leave a core port unused;
-    * reinitialise controllers to ensure that any such
-    * ports are set to 'RETRO_DEVICE_NONE' */
-   command_event(CMD_EVENT_CONTROLLER_INIT, NULL);
-
    menu_st->flags            |=  MENU_ST_FLAG_PREVENT_POPULATE
                               |  MENU_ST_FLAG_ENTRIES_NEED_REFRESH;
    return 0;
@@ -6688,8 +6683,12 @@ static size_t setting_get_string_representation_uint_input_remap_port(
       rarch_setting_t *setting, char *s, size_t len)
 {
    if (setting)
+   {
+      if (*setting->value.target.unsigned_integer == MAX_USERS)
+         return strlcpy(s, msg_hash_to_str(MENU_ENUM_LABEL_VALUE_NONE), len);
       return snprintf(s, len, "%u",
             *setting->value.target.unsigned_integer + 1);
+   }
    return 0;
 }
 
@@ -7706,11 +7705,6 @@ static int setting_action_start_input_remap_port(rarch_setting_t *setting)
     * is modified */
    input_remapping_update_port_map();
 
-   /* Changing mapped port may leave a core port unused;
-    * reinitialise controllers to ensure that any such
-    * ports are set to 'RETRO_DEVICE_NONE' */
-   command_event(CMD_EVENT_CONTROLLER_INIT, NULL);
-
    menu_st->flags            |=  MENU_ST_FLAG_PREVENT_POPULATE
                               |  MENU_ST_FLAG_ENTRIES_NEED_REFRESH;
    return 0;
@@ -7817,7 +7811,7 @@ static int setting_action_right_input_remap_port(
 
    port = setting->index_offset;
 
-   if (settings->uints.input_remap_ports[port] < MAX_USERS - 1)
+   if (settings->uints.input_remap_ports[port] < MAX_USERS)
       settings->uints.input_remap_ports[port]++;
    else
       settings->uints.input_remap_ports[port] = 0;
@@ -7826,11 +7820,6 @@ static int setting_action_right_input_remap_port(
     * is modified */
    input_remapping_update_port_map();
 
-   /* Changing mapped port may leave a core port unused;
-    * reinitialise controllers to ensure that any such
-    * ports are set to 'RETRO_DEVICE_NONE' */
-   command_event(CMD_EVENT_CONTROLLER_INIT, NULL);
-
    menu_st->flags            |=  MENU_ST_FLAG_PREVENT_POPULATE
                               |  MENU_ST_FLAG_ENTRIES_NEED_REFRESH;
    return 0;
@@ -8955,6 +8944,11 @@ static void general_write_handler(rarch_setting_t *setting)
                      NULL, menu_st->userdata);
          }
          break;
+      case MENU_ENUM_LABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS:
+         {
+            input_remapping_set_defaults(false);
+         }
+         break;
       default:
          /* Special cases */
 
@@ -8967,11 +8961,6 @@ static void general_write_handler(rarch_setting_t *setting)
             /* Must be called whenever settings->uints.input_remap_ports
              * is modified */
             input_remapping_update_port_map();
-
-            /* Changing mapped port may leave a core port unused;
-             * reinitialise controllers to ensure that any such
-             * ports are set to 'RETRO_DEVICE_NONE' */
-            command_event(CMD_EVENT_CONTROLLER_INIT, NULL);
          }
 
          break;
@@ -9802,7 +9791,7 @@ static bool setting_append_list_input_remap_port_options(
       (*list)[list_info->index - 1].action_ok     = &setting_action_ok_uint;
       (*list)[list_info->index - 1].get_string_representation =
          &setting_get_string_representation_uint_input_remap_port;
-      menu_settings_list_current_add_range(list, list_info, 0, MAX_USERS-1, 1.0, true, true);
+      menu_settings_list_current_add_range(list, list_info, 0, MAX_USERS, 1.0, true, true);
       MENU_SETTINGS_LIST_CURRENT_ADD_ENUM_IDX_PTR(list, list_info,
             (enum msg_hash_enums)(MENU_ENUM_LABEL_INPUT_REMAP_PORT + user));
    }
@@ -15641,6 +15630,22 @@ static bool setting_append_list(
                   general_read_handler,
                   SD_FLAG_ADVANCED
                   );
+            
+            CONFIG_BOOL(
+                  list, list_info,
+                  &settings->bools.input_remap_ports_on_button_press,
+                  MENU_ENUM_LABEL_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,
+                  MENU_ENUM_LABEL_VALUE_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,
+                  DEFAULT_INPUT_REMAP_PORTS_ON_BUTTON_PRESS,
+                  MENU_ENUM_LABEL_VALUE_OFF,
+                  MENU_ENUM_LABEL_VALUE_ON,
+                  &group_info,
+                  &subgroup_info,
+                  parent_group,
+                  general_write_handler,
+                  general_read_handler,
+                  SD_FLAG_ADVANCED
+                  );
 
             CONFIG_BOOL(
                   list, list_info,
@@ -17060,6 +17065,21 @@ static bool setting_append_list(
                general_read_handler,
                SD_FLAG_NONE);
 
+         CONFIG_BOOL(
+               list, list_info,
+               &settings->bools.notification_show_user_mapped_to_core_port,
+               MENU_ENUM_LABEL_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT,
+               MENU_ENUM_LABEL_VALUE_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT,
+               DEFAULT_NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT,
+               MENU_ENUM_LABEL_VALUE_OFF,
+               MENU_ENUM_LABEL_VALUE_ON,
+               &group_info,
+               &subgroup_info,
+               parent_group,
+               general_write_handler,
+               general_read_handler,
+               SD_FLAG_NONE);
+
          CONFIG_BOOL(
                list, list_info,
                &settings->bools.notification_show_config_override_load,
diff --git a/msg_hash.h b/msg_hash.h
index 8a58ffde44c..4d715c38485 100644
--- a/msg_hash.h
+++ b/msg_hash.h
@@ -262,6 +262,8 @@ enum msg_hash_enums
    MSG_DEVICE_NOT_CONFIGURED_FALLBACK_NR,
    MSG_DEVICE_DISCONNECTED_FROM_PORT, /* deprecated */
    MSG_DEVICE_DISCONNECTED_FROM_PORT_NR,
+   MSG_DEVICE_MAPPED_TO_CORE_PORT_NR,
+   MSG_PORT_MAPPED_TO_CORE_PORT_NR,
    MSG_NO_ARGUMENTS_SUPPLIED_AND_NO_MENU_BUILTIN,
    MSG_COMPILER,
    MSG_NATIVE,
@@ -1334,6 +1336,7 @@ enum msg_hash_enums
    MENU_LABEL(INPUT_BIND_TIMEOUT),
    MENU_LABEL(INPUT_BIND_HOLD),
    MENU_LABEL(INPUT_REMAP_BINDS_ENABLE),
+   MENU_LABEL(INPUT_REMAP_PORTS_ON_BUTTON_PRESS),
    MENU_LABEL(INPUT_REMAP_SORT_BY_CONTROLLER_ENABLE),
    MENU_LABEL(INPUT_OVERLAY_ENABLE),
    MENU_LABEL(INPUT_OSK_OVERLAY_ENABLE),
@@ -3841,6 +3844,7 @@ enum msg_hash_enums
    MENU_LABEL(NOTIFICATION_SHOW_CHEATS_APPLIED),
    MENU_LABEL(NOTIFICATION_SHOW_PATCH_APPLIED),
    MENU_LABEL(NOTIFICATION_SHOW_REMAP_LOAD),
+   MENU_LABEL(NOTIFICATION_SHOW_USER_MAPPED_TO_CORE_PORT),
    MENU_LABEL(NOTIFICATION_SHOW_CONFIG_OVERRIDE_LOAD),
    MENU_LABEL(NOTIFICATION_SHOW_SET_INITIAL_DISK),
    MENU_LABEL(NOTIFICATION_SHOW_DISK_CONTROL),
diff --git a/retroarch.c b/retroarch.c
index 40b44ab5edb..c45237e7a69 100644
--- a/retroarch.c
+++ b/retroarch.c
@@ -5541,7 +5541,11 @@ bool command_event(enum event_command cmd, void *data)
       case CMD_EVENT_CONTROLLER_INIT:
          {
             rarch_system_info_t *sys_info = &runloop_st->system;
-            if (sys_info)
+            bool core_inited = (runloop_st->current_core.flags & RETRO_CORE_FLAG_INITED) ? true : false;
+
+            /* Only (re)init controllers once the core is initialized otherwise the
+             * core might try to use callbacks that are not yet set. */
+            if (sys_info && core_inited)
                command_event_init_controllers(sys_info, settings,
                      settings->uints.input_max_users);
          }
diff --git a/runloop.c b/runloop.c
index 42641c182b9..bf549e6a0e6 100644
--- a/runloop.c
+++ b/runloop.c
@@ -4797,7 +4797,12 @@ bool runloop_event_init_core(
     *   at runtime should not 'bleed through' into the
     *   master config file */
    input_remapping_cache_global_config();
+
 #ifdef HAVE_CONFIGFILE
+   /* The input_remap_ports_on_button_press setting might have been changed
+    * in the config file or in the override files loaded above. */
+   input_remapping_set_remap_ports_defaults();
+
    if (auto_remaps_enable)
       config_load_remap(dir_input_remapping, &runloop_st->system);
 #endif