diff --git a/PluralKit.Bot/Commands/Api.cs b/PluralKit.Bot/Commands/Api.cs
index ad2de2ff..0b594d1c 100644
--- a/PluralKit.Bot/Commands/Api.cs
+++ b/PluralKit.Bot/Commands/Api.cs
@@ -1,3 +1,4 @@
+using System;
 using System.Text.RegularExpressions;
 using System.Threading.Tasks;
 
@@ -126,6 +127,15 @@ namespace PluralKit.Bot
             if (_webhookRegex.IsMatch(newUrl))
                 throw new PKError("PluralKit does not currently support setting a Discord webhook URL as your system's webhook URL.");
 
+            try
+            {
+                await _dispatch.DoPostRequest(ctx.System.Id, newUrl, null, true);
+            }
+            catch (Exception e)
+            {
+                throw new PKError($"Could not verify that the new URL is working: {e.Message}");
+            }
+
             var newToken = StringUtils.GenerateToken();
 
             await _repo.UpdateSystem(ctx.System.Id, new()
diff --git a/PluralKit.Core/Dispatch/DispatchService.cs b/PluralKit.Core/Dispatch/DispatchService.cs
index 367f2052..c911101b 100644
--- a/PluralKit.Core/Dispatch/DispatchService.cs
+++ b/PluralKit.Core/Dispatch/DispatchService.cs
@@ -21,7 +21,7 @@ namespace PluralKit.Core
             _provider = provider;
         }
 
-        private async Task DoPostRequest(SystemId system, string webhookUrl, HttpContent content)
+        public async Task DoPostRequest(SystemId system, string webhookUrl, HttpContent content, bool isVerify = false)
         {
             if (!await DispatchExt.ValidateUri(webhookUrl))
             {
@@ -35,7 +35,10 @@ namespace PluralKit.Core
             }
             catch (HttpRequestException e)
             {
-                _logger.Error("Could not dispatch webhook request!", e);
+                if (isVerify)
+                    throw;
+                else
+                    _logger.Error("Could not dispatch webhook request!", e);
             }
         }