diff --git a/discord/http.py b/discord/http.py
index 6a045f2f8..1e64a191f 100644
--- a/discord/http.py
+++ b/discord/http.py
@@ -224,7 +224,7 @@ class HTTPClient:
                             fmt = 'We are being rate limited. Retrying in %.2f seconds. Handled under the bucket "%s"'
 
                             # sleep a bit
-                            retry_after = data['retry_after'] / 1000.0
+                            retry_after: float = data['retry_after']  # type: ignore
                             log.warning(fmt, retry_after, bucket)
 
                             # check if it's a global rate limit
@@ -263,6 +263,7 @@ class HTTPClient:
                 except OSError as e:
                     # Connection reset by peer
                     if tries < 4 and e.errno in (54, 10054):
+                        await asyncio.sleep(1 + tries * 2)
                         continue
                     raise
 
diff --git a/discord/webhook/async_.py b/discord/webhook/async_.py
index 6a68aede5..296cccde1 100644
--- a/discord/webhook/async_.py
+++ b/discord/webhook/async_.py
@@ -165,7 +165,7 @@ class AsyncWebhookAdapter:
 
                         remaining = response.headers.get('X-Ratelimit-Remaining')
                         if remaining == '0' and response.status != 429:
-                            delta = utils._parse_ratelimit_header(response.headers)
+                            delta = utils._parse_ratelimit_header(response)
                             log.debug(
                                 'Webhook ID %s has been pre-emptively rate limited, waiting %.2f seconds', webhook_id, delta
                             )
@@ -178,9 +178,10 @@ class AsyncWebhookAdapter:
                             if not response.headers.get('Via'):
                                 raise HTTPException(response, data)
 
-                            retry_after = data['retry_after'] / 1000.0  # type: ignore
+                            retry_after: float = data['retry_after']  # type: ignore
                             log.warning('Webhook ID %s is rate limited. Retrying in %.2f seconds', webhook_id, retry_after)
                             await asyncio.sleep(retry_after)
+                            continue
 
                         if response.status >= 500:
                             await asyncio.sleep(1 + attempt * 2)
@@ -195,6 +196,7 @@ class AsyncWebhookAdapter:
 
                 except OSError as e:
                     if attempt < 4 and e.errno in (54, 10054):
+                        await asyncio.sleep(1 + attempt * 2)
                         continue
                     raise
 
diff --git a/discord/webhook/sync.py b/discord/webhook/sync.py
index b5d0bbce7..c2f4d15b4 100644
--- a/discord/webhook/sync.py
+++ b/discord/webhook/sync.py
@@ -156,7 +156,7 @@ class WebhookAdapter:
 
                         remaining = response.headers.get('X-Ratelimit-Remaining')
                         if remaining == '0' and response.status_code != 429:
-                            delta = utils._parse_ratelimit_header(response.headers)
+                            delta = utils._parse_ratelimit_header(response)
                             log.debug(
                                 'Webhook ID %s has been pre-emptively rate limited, waiting %.2f seconds', webhook_id, delta
                             )
@@ -169,9 +169,10 @@ class WebhookAdapter:
                             if not response.headers.get('Via'):
                                 raise HTTPException(response, data)
 
-                            retry_after = data['retry_after'] / 1000.0  # type: ignore
+                            retry_after: float = data['retry_after']  # type: ignore
                             log.warning('Webhook ID %s is rate limited. Retrying in %.2f seconds', webhook_id, retry_after)
                             time.sleep(retry_after)
+                            continue
 
                         if response.status_code >= 500:
                             time.sleep(1 + attempt * 2)
@@ -186,6 +187,7 @@ class WebhookAdapter:
 
                 except OSError as e:
                     if attempt < 4 and e.errno in (54, 10054):
+                        time.sleep(1 + attempt * 2)
                         continue
                     raise