diff --git a/locale/circuitpython.pot b/locale/circuitpython.pot
index 560dffe6a4..0c7f823b5a 100644
--- a/locale/circuitpython.pot
+++ b/locale/circuitpython.pot
@@ -28,14 +28,6 @@ msgid ""
 "Code stopped by auto-reload. Reloading soon.\n"
 msgstr ""
 
-#: main.c
-msgid ""
-"\n"
-"Invalid CIRCUITPY_PYSTACK_SIZE\n"
-"\n"
-"\r"
-msgstr ""
-
 #: supervisor/shared/safe_mode.c
 msgid ""
 "\n"
@@ -1252,6 +1244,10 @@ msgstr ""
 msgid "Invalid BSSID"
 msgstr ""
 
+#: main.c
+msgid "Invalid CIRCUITPY_PYSTACK_SIZE\n"
+msgstr ""
+
 #: shared-bindings/wifi/Radio.c
 msgid "Invalid MAC address"
 msgstr ""
diff --git a/main.c b/main.c
index 002c97c167..7b805b57b0 100644
--- a/main.c
+++ b/main.c
@@ -134,26 +134,18 @@ static void reset_devices(void) {
 
 #if MICROPY_ENABLE_PYSTACK
 STATIC supervisor_allocation *allocate_pystack(safe_mode_t safe_mode) {
-    mp_int_t pystack_size = CIRCUITPY_PYSTACK_SIZE;
     #if CIRCUITPY_OS_GETENV && CIRCUITPY_SETTABLE_PYSTACK
-    // Fetch value if exists from settings.toml
-    // Leaves size to build default on any failure
-    if (safe_mode == SAFE_MODE_NONE || safe_mode == SAFE_MODE_USER) {
+    if (safe_mode == SAFE_MODE_NONE) {
+        mp_int_t pystack_size = CIRCUITPY_PYSTACK_SIZE;
         (void)common_hal_os_getenv_int("CIRCUITPY_PYSTACK_SIZE", &pystack_size);
-        // Check if value is valid
-        pystack_size = pystack_size - pystack_size % sizeof(size_t); // Round down to multiple of 4.
-        if ((pystack_size < 384) || (pystack_size > 900000)) {
-            serial_write_compressed(translate("\nInvalid CIRCUITPY_PYSTACK_SIZE\n\n\r"));
-            pystack_size = CIRCUITPY_PYSTACK_SIZE; // Reset
+        supervisor_allocation *pystack = allocate_memory(pystack_size >= 384 ? pystack_size : 0, false, false);
+        if (pystack) {
+            return pystack;
         }
+        serial_write_compressed(translate("Invalid CIRCUITPY_PYSTACK_SIZE\n"));
     }
     #endif
-    supervisor_allocation *pystack = allocate_memory(pystack_size, false, false);
-    if (pystack == NULL) {
-        serial_write_compressed(translate("\nInvalid CIRCUITPY_PYSTACK_SIZE\n\n\r"));
-        pystack = allocate_memory(CIRCUITPY_PYSTACK_SIZE, false, false);
-    }
-    return pystack;
+    return allocate_memory(CIRCUITPY_PYSTACK_SIZE, false, false);
 }
 #endif
 
diff --git a/supervisor/shared/reload.c b/supervisor/shared/reload.c
index 4e351704f8..da2ffc26e1 100644
--- a/supervisor/shared/reload.c
+++ b/supervisor/shared/reload.c
@@ -82,15 +82,19 @@ inline bool autoreload_is_enabled() {
 }
 
 void autoreload_trigger() {
-    if (autoreload_enabled & !autoreload_suspended) {
-        last_autoreload_trigger = supervisor_ticks_ms32();
-        // Guard against the rare time that ticks is 0;
-        if (last_autoreload_trigger == 0) {
-            last_autoreload_trigger += 1;
-        }
-        // Initiate a reload of the VM immediately. Later code will pause to
-        // wait for the autoreload to become ready. Doing the VM exit
-        // immediately is clearer for the user.
+    if (!autoreload_enabled || autoreload_suspended != 0) {
+        return;
+    }
+    bool reload_initiated = autoreload_pending();
+    last_autoreload_trigger = supervisor_ticks_ms32();
+    // Guard against the rare time that ticks is 0;
+    if (last_autoreload_trigger == 0) {
+        last_autoreload_trigger += 1;
+    }
+    // Initiate a reload of the VM immediately. Later code will pause to
+    // wait for the autoreload to become ready. Doing the VM exit
+    // immediately is clearer for the user.
+    if (!reload_initiated) {
         reload_initiate(RUN_REASON_AUTO_RELOAD);
     }
 }
@@ -111,5 +115,5 @@ bool autoreload_ready() {
 }
 
 bool autoreload_pending(void) {
-    return last_autoreload_trigger != 0;
+    return last_autoreload_trigger > 0;
 }