diff --git a/main.c b/main.c
index c019237362..a962405498 100644
--- a/main.c
+++ b/main.c
@@ -123,7 +123,7 @@ static void reset_devices(void) {
     #endif
 }
 
-STATIC void start_mp(supervisor_allocation *heap) {
+STATIC void start_mp(supervisor_allocation *heap, bool first_run) {
     autoreload_stop();
     supervisor_workflow_reset();
 
@@ -171,7 +171,8 @@ STATIC void start_mp(supervisor_allocation *heap) {
 
     #if CIRCUITPY_ALARM
     // Record which alarm woke us up, if any. An object may be created so the heap must be functional.
-    shared_alarm_save_wake_alarm(common_hal_alarm_create_wake_alarm());
+    // There is no alarm if this is not the first time code.py or the REPL has been run.
+    shared_alarm_save_wake_alarm(first_run ? common_hal_alarm_create_wake_alarm() : mp_const_none);
     // Reset alarm module only after we retrieved the wakeup alarm.
     alarm_reset();
     #endif
@@ -309,7 +310,7 @@ STATIC void print_code_py_status_message(safe_mode_t safe_mode) {
     }
 }
 
-STATIC bool run_code_py(safe_mode_t safe_mode) {
+STATIC bool run_code_py(safe_mode_t safe_mode, bool first_run, bool *simulate_reset) {
     bool serial_connected_at_start = serial_connected();
     bool printed_safe_mode_message = false;
     #if CIRCUITPY_AUTORELOAD_DELAY_MS > 0
@@ -348,7 +349,7 @@ STATIC bool run_code_py(safe_mode_t safe_mode) {
         supervisor_allocation *heap = allocate_remaining_memory();
 
         // Prepare the VM state. Includes an alarm check/reset for sleep.
-        start_mp(heap);
+        start_mp(heap, first_run);
 
         #if CIRCUITPY_USB
         usb_setup_with_vm();
@@ -631,6 +632,8 @@ STATIC bool run_code_py(safe_mode_t safe_mode) {
     #if CIRCUITPY_ALARM
     if (fake_sleeping) {
         board_init();
+        // Pretend that the next run is the first run, as if we were reset.
+        *simulate_reset = true;
     }
     #endif
 
@@ -652,7 +655,9 @@ STATIC void __attribute__ ((noinline)) run_boot_py(safe_mode_t safe_mode) {
     // Do USB setup even if boot.py is not run.
 
     supervisor_allocation *heap = allocate_remaining_memory();
-    start_mp(heap);
+
+    // true means this is the first set of VM's after a hard reset.
+    start_mp(heap, true);
 
     #if CIRCUITPY_USB
     // Set up default USB values after boot.py VM starts but before running boot.py.
@@ -729,12 +734,12 @@ STATIC void __attribute__ ((noinline)) run_boot_py(safe_mode_t safe_mode) {
     #endif
 }
 
-STATIC int run_repl(void) {
+STATIC int run_repl(bool first_run) {
     int exit_code = PYEXEC_FORCED_EXIT;
     stack_resize();
     filesystem_flush();
     supervisor_allocation *heap = allocate_remaining_memory();
-    start_mp(heap);
+    start_mp(heap, first_run);
 
     #if CIRCUITPY_USB
     usb_setup_with_vm();
@@ -847,28 +852,34 @@ int __attribute__((used)) main(void) {
     supervisor_start_bluetooth();
     #endif
 
-    // Boot script is finished, so now go into REPL/main mode.
+    // Boot script is finished, so now go into REPL or run code.py.
     int exit_code = PYEXEC_FORCED_EXIT;
     bool skip_repl = true;
     bool first_run = true;
+    bool simulate_reset;
     for (;;) {
+        simulate_reset = false;
         if (!skip_repl) {
-            exit_code = run_repl();
+            exit_code = run_repl(first_run);
             supervisor_set_run_reason(RUN_REASON_REPL_RELOAD);
         }
         if (exit_code == PYEXEC_FORCED_EXIT) {
             if (!first_run) {
                 serial_write_compressed(translate("soft reboot\n"));
             }
-            first_run = false;
             if (pyexec_mode_kind == PYEXEC_MODE_FRIENDLY_REPL) {
-                skip_repl = run_code_py(safe_mode);
+                skip_repl = run_code_py(safe_mode, first_run, &simulate_reset);
             } else {
                 skip_repl = false;
             }
         } else if (exit_code != 0) {
             break;
         }
+
+        // Either the REPL or code.py has run and finished.
+        // If code.py did a fake deep sleep, pretend that we are running code.py for
+        // the first time after a hard reset. This will preserve any alarm information.
+        first_run = simulate_reset;
     }
     mp_deinit();
     return 0;
diff --git a/ports/espressif/common-hal/alarm/__init__.c b/ports/espressif/common-hal/alarm/__init__.c
index 8d12cb1b09..b24a91a03e 100644
--- a/ports/espressif/common-hal/alarm/__init__.c
+++ b/ports/espressif/common-hal/alarm/__init__.c
@@ -62,11 +62,6 @@ void alarm_reset(void) {
     esp_sleep_disable_wakeup_source(ESP_SLEEP_WAKEUP_ALL);
 }
 
-// This will be reset to false by full resets when bss is cleared. Otherwise, the
-// reload is due to CircuitPython and the ESP wakeup cause will be stale. This
-// can happen if USB is connected after a deep sleep.
-STATIC bool soft_wakeup = false;
-
 STATIC esp_sleep_wakeup_cause_t _get_wakeup_cause(void) {
     // First check if the modules remember what last woke up
     if (alarm_pin_pinalarm_woke_this_cycle()) {
@@ -80,11 +75,7 @@ STATIC esp_sleep_wakeup_cause_t _get_wakeup_cause(void) {
     }
     // If waking from true deep sleep, modules will have lost their state,
     // so check the deep wakeup cause manually
-    if (!soft_wakeup) {
-        soft_wakeup = true;
-        return esp_sleep_get_wakeup_cause();
-    }
-    return ESP_SLEEP_WAKEUP_UNDEFINED;
+    return esp_sleep_get_wakeup_cause();
 }
 
 bool common_hal_alarm_woken_from_sleep(void) {
diff --git a/requirements-dev.txt b/requirements-dev.txt
index 6a4f5617a8..a57794ce1a 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -2,8 +2,7 @@
 huffman
 
 # For nvm.toml
-cascadetoml==0.3.1
-tomlkit==0.7.2
+cascadetoml
 jinja2
 typer
 
diff --git a/shared-bindings/alarm/__init__.c b/shared-bindings/alarm/__init__.c
index 4160f6a334..9f9e01885a 100644
--- a/shared-bindings/alarm/__init__.c
+++ b/shared-bindings/alarm/__init__.c
@@ -64,8 +64,10 @@
 //| This object is the sole instance of `alarm.SleepMemory`."""
 //|
 
-//| wake_alarm: Alarm
-//| """The most recently triggered alarm. If CircuitPython was sleeping, the alarm the woke it from sleep."""
+//| wake_alarm: Optional[Alarm]
+//| """The most recently triggered alarm. If CircuitPython was sleeping, the alarm that woke it from sleep.
+//| If no alarm occured since the last hard reset or soft restart, value is ``None``.
+//| """
 //|
 
 // wake_alarm is implemented as a dictionary entry, so there's no code here.
@@ -103,7 +105,9 @@ STATIC mp_obj_t alarm_light_sleep_until_alarms(size_t n_args, const mp_obj_t *ar
 
     validate_objs_are_alarms(n_args, args);
 
-    return common_hal_alarm_light_sleep_until_alarms(n_args, args);
+    mp_obj_t alarm = common_hal_alarm_light_sleep_until_alarms(n_args, args);
+    shared_alarm_save_wake_alarm(alarm);
+    return alarm;
 }
 MP_DEFINE_CONST_FUN_OBJ_VAR_BETWEEN(alarm_light_sleep_until_alarms_obj, 1, MP_OBJ_FUN_ARGS_MAX, alarm_light_sleep_until_alarms);