public async Task PruneWhere(ITextChannel channel, int amount, Func <IMessage, bool> predicate) { channel.ThrowIfNull(nameof(channel)); if (amount <= 0) { throw new ArgumentOutOfRangeException(nameof(amount)); } if (!_pruningGuilds.Add(channel.GuildId)) { return; } try { IMessage[] msgs; IMessage lastMessage = null; msgs = (await channel.GetMessagesAsync(50).Flatten()).Where(predicate).Take(amount).ToArray(); while (amount > 0 && msgs.Any()) { lastMessage = msgs[msgs.Length - 1]; var bulkDeletable = new List <IMessage>(); var singleDeletable = new List <IMessage>(); foreach (var x in msgs) { if (DateTime.UtcNow - x.CreatedAt < twoWeeks) { bulkDeletable.Add(x); } else { singleDeletable.Add(x); } } if (bulkDeletable.Count > 0) { await Task.WhenAll(Task.Delay(1000), channel.DeleteMessagesAsync(bulkDeletable)).ConfigureAwait(false); } var i = 0; foreach (var group in singleDeletable.GroupBy(x => ++ i / (singleDeletable.Count / 5))) { await Task.WhenAll(Task.Delay(1000), Task.WhenAll(group.Select(x => x.DeleteAsync()))).ConfigureAwait(false); } //this isn't good, because this still work as if i want to remove only specific user's messages from the last //100 messages, Maybe this needs to be reduced by msgs.Length instead of 100 amount -= 50; if (amount > 0) { msgs = (await channel.GetMessagesAsync(lastMessage, Direction.Before, 50).Flatten()).Where(predicate).Take(amount).ToArray(); } } } catch { //ignore } finally { _pruningGuilds.TryRemove(channel.GuildId); } }