diff --git a/src/aiowebhooks/sender.py b/src/aiowebhooks/sender.py
index 30a5b18..b525ccb 100644
--- a/src/aiowebhooks/sender.py
+++ b/src/aiowebhooks/sender.py
@@ -141,8 +141,10 @@ class Webhook:
         except _Retryable as exhausted:
             return exhausted.result
         except Exception as error:
-            # never-raises net: anything else (closed session, bad proxy url, ...) -> failed result
-            log.warning("webhook send failed unexpectedly on %s: %s", url, error, exc_info=True)
+            # never-raises net: anything else (closed session, bad proxy url, ...) -> failed result.
+            # ERROR: an UNEXPECTED failure is swallowed here into a failed result (op failed, result
+            # lost, a human may need to act) - the lib is the last code that sees this exception.
+            log.error("webhook send failed unexpectedly on %s: %s", url, error, exc_info=True)
             return WebhookResult(
                 ok=False, status=None, url=url, attempts=counter[0] or 1,
                 error=f"{type(error).__name__}: {error}",
@@ -165,7 +167,8 @@ class Webhook:
             if pending_wait[0] is not None:
                 wait = pending_wait[0]
                 pending_wait[0] = None
-                log.warning("webhook 429 on %s; honoring retry_after %.3fs", url, wait)
+                log.warning("webhook 429 on %s; honoring retry_after %.3fs (attempt %d/%d)",
+                            url, wait, counter[0] + 1, self.max_retries + 1)
                 await asyncio.sleep(wait)
             counter[0] += 1
             attempts = counter[0]
@@ -174,9 +177,11 @@ class Webhook:
                 try:
                     proxy_dict = self._proxies.get()
                 except Exception:
-                    # duck-typed provider: any get() error means no proxy available
-                    log.warning("webhook: proxy get() failed; no proxy available",
-                                exc_info=True)
+                    # duck-typed provider: any get() error means no proxy available.
+                    # ERROR: swallowed into a failed result (op failed, result lost) - the
+                    # provider fault vanishes here unless it is logged loudly.
+                    log.error("webhook: proxy get() failed; no proxy available",
+                              exc_info=True)
                     return WebhookResult(
                         ok=False, status=None, url=url, attempts=attempts,
                         error="proxies unavailable", proxy=last_proxy,
@@ -209,7 +214,8 @@ class Webhook:
                         if wait is not None:
                             pending_wait[0] = wait
                         else:
-                            log.warning("webhook 429 on %s; no retry_after, backing off", url)
+                            log.warning("webhook 429 on %s; no retry_after, backing off (attempt %d/%d)",
+                                        url, attempts, self.max_retries + 1)
                         raise _Retryable(result)
                     if status >= 500:
                         raise _Retryable(result)
@@ -241,7 +247,9 @@ class Webhook:
             self._proxies.burn(proxy)
             return True
         except Exception:
-            log.warning("webhook: proxy burn failed; ending rotation", exc_info=True)
+            # ERROR: an unexpected provider fault (burn() raising) is swallowed here and ends
+            # rotation, failing the send - it must be loud, not a quiet WARNING.
+            log.error("webhook: proxy burn failed; ending rotation", exc_info=True)
             return False
 
     @staticmethod