diff --git a/Scripts/discord_webhook.py b/Scripts/discord_webhook.py
index fdf9307..58fb057 100644
--- a/Scripts/discord_webhook.py
+++ b/Scripts/discord_webhook.py
@@ -1,5 +1,7 @@
 # Minimal module-level state (only what we need)
 _CONFIG = {"discord_webhook_url": None, "discord_alert_webhook_url": None}
+# Cooldown after low-memory failures (epoch seconds)
+_NEXT_ALLOWED_SEND_TS = 0
 
 def set_config(cfg: dict):
     """Initialize module with minimal values from loaded config (call from main)."""
@@ -30,29 +32,41 @@ def send_discord_message(message, username="Auto Garden Bot", is_alert=False):
     Send Discord message with aggressive GC and low-memory guard to avoid ENOMEM.
     Returns True on success, False otherwise.
     """
+    global _NEXT_ALLOWED_SEND_TS
     resp = None
     url = _get_webhook_url(is_alert=is_alert)
     if not url:
         return False
 
+    # Respect cooldown if we recently saw ENOMEM
+    try:
+        import time  # type: ignore
+        now = time.time()
+        if _NEXT_ALLOWED_SEND_TS and now < _NEXT_ALLOWED_SEND_TS:
+            return False
+    except:
+        pass
+
     try:
         # 1) Free heap before TLS
         import gc  # type: ignore
         gc.collect()
         try:
             # If MicroPython provides mem_free, skip send if heap is very low
-            if hasattr(gc, "mem_free") and gc.mem_free() < 60000:  # ~60KB threshold
+            # TLS can be spiky and fragmented; be conservative.
+            if hasattr(gc, "mem_free") and gc.mem_free() < 100000:  # ~100KB threshold
                 return False
         except:
             pass
 
         # 2) Import urequests locally (keeps RAM free when idle)
         import urequests as requests  # type: ignore
+        gc.collect()  # collect again after import to reduce fragmentation
 
         # 3) Keep payload tiny
         url = str(url).strip().strip('\'"')
-        content = _escape_json_str(str(message)[:160])
-        user = _escape_json_str(str(username)[:40])
+        content = _escape_json_str(str(message)[:140])  # trim further
+        user = _escape_json_str(str(username)[:32])
         body_bytes = ('{"content":"%s","username":"%s"}' % (content, user)).encode("utf-8")
 
         # Minimal headers to reduce allocations
@@ -65,6 +79,13 @@ def send_discord_message(message, username="Auto Garden Bot", is_alert=False):
         return bool(status and 200 <= status < 300)
 
     except Exception as e:
+        # On ENOMEM/MemoryError, back off for 30 seconds to avoid repeated failures
+        try:
+            if ("ENOMEM" in str(e)) or isinstance(e, MemoryError):
+                import time  # type: ignore
+                _NEXT_ALLOWED_SEND_TS = time.time() + 30
+        except:
+            pass
         print("Discord webhook exception:", e)
         return False
 
@@ -76,7 +97,7 @@ def send_discord_message(message, username="Auto Garden Bot", is_alert=False):
             pass
         # Free refs and force GC
         try:
-            del resp, body_bytes
+            del resp, body_bytes, requests
         except:
             pass
         try:
diff --git a/main.py b/main.py
index 4891bb6..99fe67a 100644
--- a/main.py
+++ b/main.py
@@ -202,6 +202,7 @@ if wifi and wifi.isconnected():
     
     # Send startup notification to Discord (with timeout, non-blocking)
     try:
+        gc.collect()  # free heap before HTTPS
         success = discord_webhook.send_discord_message(f"Pico W online at http://{ifconfig[0]} ✅")
         if success:
             print("Discord startup notification sent")