diff --git a/PluralKit.Bot/Services/WebhookCacheService.cs b/PluralKit.Bot/Services/WebhookCacheService.cs
index 873f8eba..8967ee61 100644
--- a/PluralKit.Bot/Services/WebhookCacheService.cs
+++ b/PluralKit.Bot/Services/WebhookCacheService.cs
@@ -40,9 +40,26 @@ namespace PluralKit.Bot
             // We cache the webhook through a Lazy<Task<T>>, this way we make sure to only create one webhook per channel
             // If the webhook is requested twice before it's actually been found, the Lazy<T> wrapper will stop the
             // webhook from being created twice.
-            var lazyWebhookValue =    
-                _webhooks.GetOrAdd(channel.Id, new Lazy<Task<DiscordWebhook>>(() => GetOrCreateWebhook(channel)));
+            Lazy<Task<DiscordWebhook>> GetWebhookTaskInner()
+            {
+                Task<DiscordWebhook> Factory() => GetOrCreateWebhook(channel);
+                return _webhooks.GetOrAdd(channel.Id, new Lazy<Task<DiscordWebhook>>(Factory));
+            }
+            var lazyWebhookValue = GetWebhookTaskInner();
             
+            // If we've cached a failed Task, we need to clear it and try again
+            // This is so errors don't become "sticky" and *they* in turn get cached (not good)
+            // although, keep in mind this block gets hit the call *after* the task failed (since we only await it below)
+            if (lazyWebhookValue.IsValueCreated && lazyWebhookValue.Value.IsFaulted)
+            {
+                _logger.Warning(lazyWebhookValue.Value.Exception, "Cached webhook task for {Channel} faulted with below exception");
+                
+                // Specifically don't recurse here so we don't infinite-loop - if this one errors too, it'll "stick"
+                // until next time this function gets hit (which is okay, probably).
+                _webhooks.TryRemove(channel.Id, out _);
+                lazyWebhookValue = GetWebhookTaskInner();
+            }
+
             // It's possible to "move" a webhook to a different channel after creation
             // Here, we ensure it's actually still pointing towards the proper channel, and if not, wipe and refetch one.
             var webhook = await lazyWebhookValue.Value;