diff --git a/RhinoReminds/ClientListener.cs b/RhinoReminds/ClientListener.cs
index f51b7da..eb8252b 100644
--- a/RhinoReminds/ClientListener.cs
+++ b/RhinoReminds/ClientListener.cs
@@ -33,7 +33,8 @@ namespace RhinoReminds
 
 		public string ReminderFilePath { get; set; } = "./reminders.xml";
 		private ReminderList reminderList = new ReminderList();
-
+		private CancellationTokenSource reminderWatcherReset;
+		private CancellationToken reminderWatcherResetToken;
 
 		private SimpleXmppClient client;
 		/// <summary>
@@ -224,6 +225,8 @@ namespace RhinoReminds
 						client.SendChatReply(message, response);
 					}
 					if (succeeded.Count > 0) {
+						// Ensure that the reminder thread picks up the changes
+						resetReminderWatcher();
 						string response = string.Join(", ", succeeded.Select((int nextId) => $"#{nextId}"));
 						response = $"Deleted reminder{(succeeded.Count != 1 ? "s" : "")} {response} successfully.";
 						client.SendChatReply(message, response);
@@ -299,10 +302,16 @@ namespace RhinoReminds
 
 		#region Reminder Listening
 
+		private void resetReminderWatcher()
+		{
+			// We don't need to create a new token here, as the watcher does thisi automagically
+			reminderWatcherReset.Cancel();
+		}
+
 		private async Task watchForReminders()
 		{
-			CancellationTokenSource cancellationSource = new CancellationTokenSource();
-			CancellationToken cancellationToken = cancellationSource.Token;
+			reminderWatcherReset = new CancellationTokenSource();
+			reminderWatcherResetToken = reminderWatcherReset.Token;
 			Reminder nextReminder = reminderList.GetNextReminder();
 			reminderList.OnReminderListUpdate += (object sender, Reminder newReminder) => {
 				Reminder newNextReminder = reminderList.GetNextReminder();
@@ -311,7 +320,7 @@ namespace RhinoReminds
 				if (nextReminder != newNextReminder) {
 					//Console.WriteLine($"[Rhino/Reminderd/Canceller] Cancelling");
 					nextReminder = newNextReminder;
-					cancellationSource.Cancel();
+					reminderWatcherReset.Cancel();
 				}
 			};
 
@@ -323,23 +332,23 @@ namespace RhinoReminds
 						nextWaitingTime = nextReminder.Time - DateTime.Now;
 						if (DateTime.Now < nextReminder.Time) {
 							//Console.WriteLine($"[Rhino/Reminderd] Sleeping for {nextWaitingTime}");
-							await Task.Delay(nextWaitingTime, cancellationToken);
+							await Task.Delay(nextWaitingTime, reminderWatcherResetToken);
 						}
 					} else {
 						//Console.WriteLine("[Rhino/Reminderd] Sleeping until interrupted");
-						await Task.Delay(Timeout.Infinite, cancellationToken);
+						await Task.Delay(Timeout.Infinite, reminderWatcherResetToken);
 					}
 				} catch (TaskCanceledException) {
 					//Console.WriteLine("[Rhino/Reminderd] Sleep interrupted, recalculating");
-					cancellationSource = new CancellationTokenSource();
-					cancellationToken = cancellationSource.Token;
+					reminderWatcherReset = new CancellationTokenSource();
+					reminderWatcherResetToken = reminderWatcherReset.Token;
 					continue;
 				}
 
-				if (cancellationToken.IsCancellationRequested) {
+				if (reminderWatcherResetToken.IsCancellationRequested) {
 					Console.WriteLine("[Rhino/Reminderd] Sleep interrupted, recalculating (but no exception thrown)");
-					cancellationSource = new CancellationTokenSource();
-					cancellationToken = cancellationSource.Token;
+					reminderWatcherReset = new CancellationTokenSource();
+					reminderWatcherResetToken = reminderWatcherReset.Token;
 
 					continue;
 				}