diff --git a/BotFeature.cs b/BotFeature.cs
index e3fcf08..deb9c57 100644
--- a/BotFeature.cs
+++ b/BotFeature.cs
@@ -18,6 +18,7 @@ namespace Noikoio.RegexBot
         private readonly AsyncLogger _logger;
         
         public abstract string Name { get; }
+        protected DiscordSocketClient Client => _client;
 
         protected BotFeature(DiscordSocketClient client)
         {
@@ -60,6 +61,20 @@ namespace Noikoio.RegexBot
             if (sc.FeatureConfigs.TryGetValue(this, out var item)) return item;
             else return null;
         }
+
+        /// <summary>
+        /// Determines if the given message author or channel is in the server configuration's moderator list.
+        /// </summary>
+        protected bool IsModerator(ulong guildId, SocketMessage m)
+        {
+            var sc = RegexBot.Config.Servers.FirstOrDefault(g => g.Id == guildId);
+            if (sc == null)
+            {
+                throw new ArgumentException("There is no known configuration associated with the given Guild ID.");
+            }
+
+            return sc.Moderators.ExistsInList(m);
+        }
         
         protected async Task Log(string text)
         {
diff --git a/Feature/AutoMod/AutoMod.cs b/Feature/AutoMod/AutoMod.cs
index bc60378..2b2588d 100644
--- a/Feature/AutoMod/AutoMod.cs
+++ b/Feature/AutoMod/AutoMod.cs
@@ -1,31 +1,96 @@
-using System;
-using System.Collections.Generic;
-using System.Text;
-using System.Threading.Tasks;
-using Discord.WebSocket;
+using Discord.WebSocket;
 using Newtonsoft.Json.Linq;
+using Noikoio.RegexBot.Feature.AutoMod.Responses;
+using System;
+using System.Collections.Generic;
+using System.Threading.Tasks;
 
 namespace Noikoio.RegexBot.Feature.AutoMod
 {
     /// <summary>
     /// Implements per-message regex matching and executes customizable responses.
     /// The name RegexBot comes from the existence of this feature.
-    /// 
-    /// Strictly for use as a moderation tool only. Triggers that respond only to messages
-    /// should be configured using <see cref="AutoRespond"/>.
     /// </summary>
+    /// <remarks>
+    /// Strictly for use as a moderation tool only. Triggers that simply reply to messages
+    /// should be implemented using <see cref="AutoRespond"/>.
+    /// </remarks>
     class AutoMod : BotFeature
     {
         public override string Name => "AutoMod";
 
         public AutoMod(DiscordSocketClient client) : base(client)
         {
-            throw new NotImplementedException();
+            client.MessageReceived += CMessageReceived;
+            client.MessageUpdated += CMessageUpdated;
         }
 
-        public override Task<object> ProcessConfiguration(JToken configSection)
+        [ConfigSection("automod")]
+        public override async Task<object> ProcessConfiguration(JToken configSection)
         {
-            throw new NotImplementedException();
+            List<Rule> rules = new List<Rule>();
+            foreach (JObject ruleconf in configSection)
+            {
+                var rule = new Rule(this, ruleconf);
+                rules.Add(rule);
+                await Log($"Added rule '{rule.Label}'");
+            }
+            return rules.AsReadOnly();
         }
+
+        private async Task CMessageReceived(SocketMessage arg)
+            => await ReceiveMessage(arg);
+        private async Task CMessageUpdated(Discord.Cacheable<Discord.IMessage, ulong> arg1, SocketMessage arg2, ISocketMessageChannel arg3)
+            => await ReceiveMessage(arg2);
+
+        /// <summary>
+        /// Does initial message checking before sending to further processing.
+        /// </summary>
+        private async Task ReceiveMessage(SocketMessage m)
+        {
+            // Determine if incoming channel is in a guild
+            var ch = m.Channel as SocketGuildChannel;
+            if (ch == null) return;
+
+            // Get rules
+            var rules = GetConfig(ch.Guild.Id) as IEnumerable<Rule>;
+            if (rules == null) return;
+
+            foreach (var rule in rules)
+            {
+                // Checking for mod bypass here (Rule doesn't have access to mod list)
+                bool isMod = IsModerator(ch.Guild.Id, m);
+                //await Task.Run(async () => await ProcessMessage(m, rule, isMod));
+                await ProcessMessage(m, rule, isMod);
+            }
+        }
+
+        /// <summary>
+        /// Checks if the incoming message matches the given rule, and executes responses if necessary. 
+        /// </summary>
+        private async Task ProcessMessage(SocketMessage m, Rule r, bool isMod)
+        {
+            if (!r.Match(m, isMod)) return;
+
+            // TODO make log optional; configurable
+            await Log($"{r} triggered by {m.Author.ToString()}");
+
+            foreach (Response resp in r.Response)
+            {
+                // TODO foreach await (when that becomes available)
+                try
+                {
+                    await resp.Invoke(m);
+                }
+                catch (Exception ex)
+                {
+                    await Log($"Encountered an error while processing '{resp.CmdArg0}'. Details follow:");
+                    await Log(ex.ToString());
+                }
+            }
+        }
+
+        public new Task Log(string text) => base.Log(text);
+        public new DiscordSocketClient Client => base.Client;
     }
 }
diff --git a/Feature/AutoMod/Responses/Ban.cs b/Feature/AutoMod/Responses/Ban.cs
new file mode 100644
index 0000000..41b7139
--- /dev/null
+++ b/Feature/AutoMod/Responses/Ban.cs
@@ -0,0 +1,50 @@
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Bans the invoking user.
+    /// Parameters: ban [days = 0]
+    /// </summary>
+    class Ban : Response
+    {
+        readonly int _purgeDays;
+
+        public Ban(Rule rule, string cmdline) : base(rule, cmdline)
+        {
+            var line = cmdline.Split(new char[] { ' ' }, StringSplitOptions.RemoveEmptyEntries);
+            if (line.Length == 1)
+            {
+                _purgeDays = 0;
+            }
+            else if (line.Length == 2)
+            {
+                if (int.TryParse(line[1], out _purgeDays))
+                {
+                    if (_purgeDays < 0 || _purgeDays > 7)
+                    {
+                        throw new RuleImportException("Parameter must be an integer between 0 and 7.");
+                    }
+                }
+                else
+                {
+                    throw new RuleImportException("Parameter must be an integer between 0 and 7.");
+                }
+            }
+            else
+            {
+                throw new RuleImportException("Incorrect number of parameters.");
+            }
+        }
+
+        public override async Task Invoke(SocketMessage msg)
+        {
+            var target = (SocketGuildUser)msg.Author;
+            await target.Guild.AddBanAsync(target, _purgeDays, Uri.EscapeDataString($"Rule '{Rule.Label}'"));
+            // TODO remove string escaping when fixed in library
+        }
+    }
+}
diff --git a/Feature/AutoMod/Responses/Kick.cs b/Feature/AutoMod/Responses/Kick.cs
new file mode 100644
index 0000000..df43cfe
--- /dev/null
+++ b/Feature/AutoMod/Responses/Kick.cs
@@ -0,0 +1,28 @@
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Kicks the invoking user.
+    /// Takes no parameters.
+    /// </summary>
+    class Kick : Response
+    {
+        public Kick(Rule rule, string cmdline) : base(rule, cmdline)
+        {
+            // Throw exception if extra parameters found
+            if (cmdline.Split(new char[] { ' ' }, StringSplitOptions.RemoveEmptyEntries).Length > 1)
+                throw new RuleImportException("Incorrect number of parameters.");
+        }
+
+        public override async Task Invoke(SocketMessage msg)
+        {
+            var target = (SocketGuildUser)msg.Author;
+            await target.KickAsync(Uri.EscapeDataString($"Rule '{Rule.Label}'"));
+            // TODO remove string escaping when fixed in library
+        }
+    }
+}
diff --git a/Feature/AutoMod/Responses/Remove.cs b/Feature/AutoMod/Responses/Remove.cs
new file mode 100644
index 0000000..7f4d949
--- /dev/null
+++ b/Feature/AutoMod/Responses/Remove.cs
@@ -0,0 +1,23 @@
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Removes the invoking message.
+    /// Takes no parameters.
+    /// </summary>
+    class Remove : Response
+    {
+        public Remove(Rule rule, string cmdline) : base(rule, cmdline)
+        {
+            // Throw exception if extra parameters found
+            if (cmdline.Split(new char[] { ' ' }, StringSplitOptions.RemoveEmptyEntries).Length > 1)
+                throw new RuleImportException("Incorrect number of parameters.");
+        }
+
+        public override Task Invoke(SocketMessage msg) => msg.DeleteAsync();
+    }
+}
diff --git a/Feature/AutoMod/Responses/Report.cs b/Feature/AutoMod/Responses/Report.cs
new file mode 100644
index 0000000..00efe50
--- /dev/null
+++ b/Feature/AutoMod/Responses/Report.cs
@@ -0,0 +1,93 @@
+using Discord;
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Text;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Sends a summary of the invoking message, along with information
+    /// about the rule making use of this command, to the given target.
+    /// Parameters: report (target)
+    /// </summary>
+    class Report : Response
+    {
+        readonly string _target;
+
+        public Report(Rule rule, string cmdline) : base(rule, cmdline)
+        {
+            var line = cmdline.Split(new char[] { ' ' }, StringSplitOptions.RemoveEmptyEntries);
+            if (line.Length != 2) throw new RuleImportException("Incorrect number of parameters");
+            _target = line[1];
+        }
+
+        public override async Task Invoke(SocketMessage msg)
+        {
+            var target = await GetMessageTargetAsync(_target, msg);
+            if (target == null)
+            {
+                await Log("Error: Unable to resolve the given target.");
+            }
+            await target.SendMessageAsync("", embed: BuildReportEmbed(msg));
+        }
+
+        private EmbedBuilder BuildReportEmbed(SocketMessage msg)
+        {
+            string invokeLine = msg.Content;
+
+            var responsebody = new StringBuilder();
+            responsebody.AppendLine("```");
+            foreach (var item in Rule.Response)
+            {
+                responsebody.AppendLine(item.CmdLine.Replace("\r", "").Replace("\n", "\\n"));
+            }
+            responsebody.Append("```");
+
+            // Discord has a 2000 character limit per single message.
+            // Enforcing separate length limits on line and response.
+            const int DescriptionLengthMax = 1600;
+            const int ResponseBodyLengthMax = 200;
+            if (invokeLine.Length > DescriptionLengthMax)
+            {
+                invokeLine = $"**Message length too long; showing first {DescriptionLengthMax} characters.**\n\n"
+                    + invokeLine.Substring(0, DescriptionLengthMax);
+            }
+            if (responsebody.Length > ResponseBodyLengthMax)
+            {
+                responsebody = new StringBuilder("(Response body too large to display.)");
+            }
+
+            return new EmbedBuilder()
+            {
+                Color = new Color(0xEDCE00), // configurable later?
+
+                Author = new EmbedAuthorBuilder()
+                {
+                    Name = $"{msg.Author.Username}#{msg.Author.Discriminator} said:",
+                    IconUrl = msg.Author.GetAvatarUrl()
+                },
+                Description = invokeLine,
+
+                Footer = new EmbedFooterBuilder()
+                {
+                    Text = $"Rule '{Rule.Label}'",
+                    IconUrl = Rule.Discord.CurrentUser.GetAvatarUrl()
+                },
+                Timestamp = msg.EditedTimestamp ?? msg.Timestamp
+            }.AddField(new EmbedFieldBuilder()
+            {
+                Name = "Additional info",
+                Value = $"Username: {msg.Author.Mention}\n"
+                + $"Channel: <#{msg.Channel.Id}> #{msg.Channel.Name} ({msg.Channel.Id})\n"
+                + $"Message ID: {msg.Id}"
+            }).AddField(new EmbedFieldBuilder()
+            {
+                // TODO consider replacing with configurable note. this section is a bit too much
+                Name = "Executing response:",
+                Value = responsebody.ToString()
+            });
+        }
+    }
+}
diff --git a/Feature/AutoMod/Responses/Response.cs b/Feature/AutoMod/Responses/Response.cs
new file mode 100644
index 0000000..5149aed
--- /dev/null
+++ b/Feature/AutoMod/Responses/Response.cs
@@ -0,0 +1,171 @@
+using Discord;
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Collections.Generic;
+using System.Collections.ObjectModel;
+using System.Diagnostics;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Base class for all Response classes.
+    /// Contains helper methods for use by response code.
+    /// </summary>
+    [DebuggerDisplay("Response: {_cmdline}")]
+    abstract class Response
+    {
+        private readonly Rule _rule;
+        private readonly string _cmdline;
+        
+        protected Rule Rule => _rule;
+        private DiscordSocketClient Client => _rule.Discord;
+        public string CmdLine => _cmdline;
+        public string CmdArg0 {
+            get {
+                int i = _cmdline.IndexOf(' ');
+                if (i != -1) return _cmdline.Substring(0, i);
+                return _cmdline;
+            }
+        }
+
+        /// <summary>
+        /// Deriving constructor should do validation of incoming <paramref name="cmdline"/>.
+        /// </summary>
+        public Response(Rule rule, string cmdline)
+        {
+            _rule = rule;
+            _cmdline = cmdline;
+        }
+
+        public abstract Task Invoke(SocketMessage msg);
+
+        protected async Task Log(string text)
+        {
+            int dl = _cmdline.IndexOf(' ');
+            var prefix = _cmdline.Substring(0, dl);
+            await Rule.Logger(prefix + ": " + text);
+        }
+
+        #region Config loading
+        private static readonly ReadOnlyDictionary<string, Type> _commands =
+            new ReadOnlyDictionary<string, Type>(
+            new Dictionary<string, Type>(StringComparer.OrdinalIgnoreCase)
+            {
+                // Define all accepted commands and their corresponding types here
+                { "say", typeof(Say) },
+                { "send", typeof(Say) },
+                { "report", typeof(Report) },
+                { "addrole", typeof(RoleManipulation) },
+                { "grantrole", typeof(RoleManipulation) },
+                { "delrole", typeof(RoleManipulation) },
+                { "removerole", typeof(RoleManipulation) },
+                { "revokerole", typeof(RoleManipulation) },
+                { "delete", typeof(Remove) },
+                { "remove", typeof(Remove) },
+                { "kick", typeof(Kick) },
+                { "ban", typeof(Ban) }
+            });
+
+        public static Response[] ReadConfiguration(Rule r, IEnumerable<string> responses)
+        {
+            var result = new List<Response>();
+            foreach (var line in responses)
+            {
+                if (string.IsNullOrWhiteSpace(line))
+                    throw new RuleImportException("Empty response line");
+                int i = line.IndexOf(' ');
+                string basecmd;
+                if (i != -1) basecmd = line.Substring(0, i);
+                else basecmd = line;
+
+                Type rt;
+                if (!_commands.TryGetValue(basecmd, out rt))
+                    throw new RuleImportException($"'{basecmd}' is not a valid response");
+
+                var newresponse = Activator.CreateInstance(rt, r, line) as Response;
+                if (newresponse == null)
+                    throw new Exception("An unknown error occurred when attempting to create a new Response object.");
+                result.Add(newresponse);
+            }
+            return result.ToArray();
+        }
+        #endregion
+
+        #region Helper methods
+        /// <summary>
+        /// Receives a string (beginning with @ or #) and returns an object
+        /// suitable for sending out messages
+        /// </summary>
+        protected async Task<IMessageChannel> GetMessageTargetAsync(string targetName, SocketMessage m)
+        {
+            const string AEShort = "Target name is too short.";
+
+            EntityType et;
+            if (targetName.Length <= 1) throw new ArgumentException(AEShort);
+
+            if (targetName[0] == '#') et = EntityType.Channel;
+            else if (targetName[0] == '@') et = EntityType.User;
+            else throw new ArgumentException("Target is not specified to be either a channel or user.");
+
+            targetName = targetName.Substring(1);
+            if (targetName == "_")
+            {
+                if (et == EntityType.Channel) return m.Channel;
+                else return await m.Author.GetOrCreateDMChannelAsync();
+            }
+
+            EntityName ei = new EntityName(targetName, et);
+            SocketGuild g = ((SocketGuildUser)m.Author).Guild;
+
+            if (et == EntityType.Channel)
+            {
+                if (targetName.Length < 2 || targetName.Length > 100)
+                    throw new ArgumentException(AEShort);
+
+                foreach (var ch in g.TextChannels)
+                {
+                    if (ei.Id.HasValue)
+                    {
+                        if (ei.Id.Value == ch.Id) return ch;
+                    }
+                    else
+                    {
+                        if (string.Equals(ei.Name, ch.Name, StringComparison.OrdinalIgnoreCase)) return ch;
+                    }
+                }
+            }
+            else
+            {
+                if (ei.Id.HasValue)
+                {
+                    // The easy way
+                    return await Client.GetUser(ei.Id.Value).GetOrCreateDMChannelAsync();
+                }
+
+                // The hard way
+                foreach (var u in g.Users)
+                {
+                    if (string.Equals(ei.Name, u.Username, StringComparison.OrdinalIgnoreCase) ||
+                        string.Equals(ei.Name, u.Nickname, StringComparison.OrdinalIgnoreCase))
+                    {
+                        return await u.GetOrCreateDMChannelAsync();
+                    }
+                }
+            }
+
+            return null;
+        }
+
+        protected string ProcessText(string input, SocketMessage m)
+        {
+            // Maybe in the future this will do more.
+            // For now, replaces all instances of @_ with the message sender.
+            return input
+                .Replace("@_", m.Author.Mention)
+                .Replace("@\\_", "@_");
+        }
+        #endregion
+    }
+}
diff --git a/Feature/AutoMod/Responses/RoleManipulation.cs b/Feature/AutoMod/Responses/RoleManipulation.cs
new file mode 100644
index 0000000..3fd57ba
--- /dev/null
+++ b/Feature/AutoMod/Responses/RoleManipulation.cs
@@ -0,0 +1,89 @@
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Linq;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Manipulates a given user's role.
+    /// Parameters: (command) (target) (role ID)
+    /// </summary>
+    class RoleManipulation : Response
+    {
+        enum ManipulationType { None, Add, Remove }
+
+        readonly ManipulationType _action;
+        readonly string _target;
+        readonly EntityName _role;
+
+        public RoleManipulation(Rule rule, string cmdline) : base(rule, cmdline)
+        {
+            var line = cmdline.Split(new char[] { ' ' }, StringSplitOptions.RemoveEmptyEntries);
+            if (line.Length != 3)
+                throw new RuleImportException("Incorrect number of parameters.");
+
+            // Ensure the strings here match those in Response._commands
+            switch (line[0].ToLowerInvariant())
+            {
+                case "addrole":
+                case "grantrole":
+                    _action = ManipulationType.Add;
+                    break;
+                case "delrole":
+                case "removerole":
+                case "revokerole":
+                    _action = ManipulationType.Remove;
+                    break;
+                default:
+                    _action = ManipulationType.None;
+                    break;
+            }
+            if (_action == ManipulationType.None)
+                throw new RuleImportException("Command not defined. This is a bug.");
+
+            _target = line[1];
+            _role = new EntityName(line[2], EntityType.Role);
+        }
+
+        public override async Task Invoke(SocketMessage msg)
+        {
+            // Find role
+            SocketRole rtarget;
+            var g = ((SocketGuildUser)msg.Author).Guild;
+            if (_role.Id.HasValue) rtarget = g.GetRole(_role.Id.Value);
+            else rtarget = g.Roles.FirstOrDefault(r =>
+                string.Equals(r.Name, _role.Name, StringComparison.OrdinalIgnoreCase));
+            if (rtarget == null)
+            {
+                await Log("Error: Target role not found in server.");
+                return;
+            }
+
+            // Find user
+            SocketGuildUser utarget;
+            if (_target == "@_") utarget = (SocketGuildUser)msg.Author;
+            else
+            {
+                utarget = g.Users.FirstOrDefault(u =>
+                {
+                    if (string.Equals(u.Nickname, _target, StringComparison.OrdinalIgnoreCase)) return true;
+                    if (string.Equals(u.Username, _target, StringComparison.OrdinalIgnoreCase)) return true;
+                    return false;
+                });
+            }
+            if (utarget == null)
+            {
+                await Log("Error: Target user not found in server.");
+                return;
+            }
+
+            // Do action
+            if (_action == ManipulationType.Add)
+                await utarget.AddRoleAsync(rtarget);
+            else if (_action == ManipulationType.Remove)
+                await utarget.RemoveRoleAsync(rtarget);
+        }
+    }
+}
diff --git a/Feature/AutoMod/Responses/Say.cs b/Feature/AutoMod/Responses/Say.cs
new file mode 100644
index 0000000..3dcbc8e
--- /dev/null
+++ b/Feature/AutoMod/Responses/Say.cs
@@ -0,0 +1,45 @@
+using Discord.WebSocket;
+using Noikoio.RegexBot.ConfigItem;
+using System;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod.Responses
+{
+    /// <summary>
+    /// Sends a message to the given target.
+    /// Parameters: say (target) (message)
+    /// </summary>
+    class Say : Response
+    {
+        private readonly string _target;
+        private readonly string _payload;
+
+        public Say(Rule rule, string cmdline) : base(rule, cmdline)
+        {
+            var line = cmdline.Split(new char[] { ' ' }, 3, StringSplitOptions.RemoveEmptyEntries);
+            if (line.Length != 3) throw new RuleImportException("Incorrect number of parameters.");
+
+            // Very basic target verification. Could be improved?
+            if (line[1][0] != '@' && line[1][0] != '#')
+                throw new RuleImportException("The given target is not valid.");
+            _target = line[1];
+
+            _payload = line[2];
+            if (string.IsNullOrWhiteSpace(_payload))
+                throw new RuleImportException("Message parameter is blank or missing.");
+        }
+
+        public override async Task Invoke(SocketMessage msg)
+        {
+            // ＣＨＡＮＧＥ  ＴＨＥ  ＳＡＹ
+            string reply = ProcessText(_payload, msg);
+
+            var target = await GetMessageTargetAsync(_target, msg);
+            if (target == null)
+            {
+                await Log("Error: Unable to resolve the given target.");
+            }
+            await target.SendMessageAsync(reply);
+        }
+    }
+}
diff --git a/Feature/AutoMod/Rule.cs b/Feature/AutoMod/Rule.cs
new file mode 100644
index 0000000..3c494a5
--- /dev/null
+++ b/Feature/AutoMod/Rule.cs
@@ -0,0 +1,212 @@
+using Discord;
+using Discord.WebSocket;
+using Newtonsoft.Json.Linq;
+using Noikoio.RegexBot.ConfigItem;
+using Noikoio.RegexBot.Feature.AutoMod.Responses;
+using System;
+using System.Collections.Generic;
+using System.Text;
+using System.Text.RegularExpressions;
+using System.Threading.Tasks;
+
+namespace Noikoio.RegexBot.Feature.AutoMod
+{
+    /// <summary>
+    /// Representation of a single AutoMod rule.
+    /// Data stored within cannot be edited.
+    /// </summary>
+    class Rule
+    {
+        readonly AutoMod _instance;
+        readonly string _label;
+        readonly IEnumerable<Regex> _regex;
+        readonly ICollection<Response> _responses;
+        readonly FilterList _filter;
+        readonly int _msgMinLength;
+        readonly int _msgMaxLength;
+        readonly bool _modBypass;
+        readonly bool _embedMode;
+
+        public string Label => _label;
+        public IEnumerable<Regex> Regex => _regex;
+        public ICollection<Response> Response => _responses;
+        public FilterList Filter => _filter;
+        public (int?, int?) MatchLengthMinMaxLimit => (_msgMinLength, _msgMaxLength);
+        public bool AllowsModBypass => _modBypass;
+        public bool MatchEmbed => _embedMode;
+
+        public DiscordSocketClient Discord => _instance.Client;
+        public Func<string, Task> Logger => _instance.Log;
+
+        /// <summary>
+        /// Creates a new Rule instance to represent the given configuration.
+        /// </summary>
+        public Rule(AutoMod instance, JObject ruleconf)
+        {
+            _instance = instance;
+
+            _label = ruleconf["label"]?.Value<string>();
+            if (string.IsNullOrEmpty(_label))
+                throw new RuleImportException("Label not defined.");
+
+            string errpfx = $" in definition for rule '{_label}'.";
+
+            // regex options
+            RegexOptions opts = RegexOptions.Compiled | RegexOptions.CultureInvariant;
+            // TODO consider adding an option to specify Singleline and Multiline matching
+            opts |= RegexOptions.Singleline;
+            // case sensitivity must be explicitly defined, else not case sensitive by default
+            bool? regexci = ruleconf["ignorecase"]?.Value<bool>();
+            opts |= RegexOptions.IgnoreCase;
+            if (regexci.HasValue && regexci.Value == false)
+                opts &= ~RegexOptions.IgnoreCase;
+
+            // regex
+            const string NoRegexError = "No regular expression patterns are defined";
+            var regexes = new List<Regex>();
+            var rxconf = ruleconf["regex"];
+            if (rxconf == null) throw new RuleImportException(NoRegexError + errpfx);
+            if (rxconf.Type == JTokenType.Array)
+            {
+                foreach (var input in rxconf.Values<string>())
+                {
+                    try
+                    {
+                        Regex r = new Regex(input, opts);
+                        regexes.Add(r);
+                    }
+                    catch (ArgumentException)
+                    {
+                        throw new RuleImportException(
+                            $"Failed to parse regular expression pattern '{input}'{errpfx}");
+                    }
+                }
+            }
+            else
+            {
+                string rxstr = rxconf.Value<string>();
+                try
+                {
+                    Regex r = new Regex(rxstr, opts);
+                    regexes.Add(r);
+                }
+                catch (Exception ex) when (ex is ArgumentException || ex is NullReferenceException)
+                {
+                    throw new RuleImportException(
+                        $"Failed to parse regular expression pattern '{rxstr}'{errpfx}");
+                }
+            }
+            if (regexes.Count == 0)
+            {
+                throw new RuleImportException(NoRegexError + errpfx);
+            }
+            _regex = regexes.ToArray();
+
+            // min/max length
+            try
+            {
+                _msgMinLength = ruleconf["min"]?.Value<int>() ?? -1;
+                _msgMaxLength = ruleconf["max"]?.Value<int>() ?? -1;
+            }
+            catch (FormatException)
+            {
+                throw new RuleImportException("Minimum/maximum values must be an integer.");
+            }
+
+            // responses
+            const string NoResponseError = "No responses have been defined";
+            var responsestrs = new List<string>();
+            var rsconf = ruleconf["response"];
+            if (rsconf == null) throw new RuleImportException(NoResponseError + errpfx);
+            try
+            {
+                if (rsconf.Type == JTokenType.Array)
+                {
+                    _responses = Responses.Response.ReadConfiguration(this, rsconf.Values<string>());
+                }
+                else
+                {
+                    _responses = Responses.Response.ReadConfiguration(this, new string[] { rsconf.Value<string>() });
+                }
+            }
+            catch (RuleImportException ex)
+            {
+                throw new RuleImportException(ex.Message + errpfx);
+            }
+            
+
+            // whitelist/blacklist filtering
+            _filter = new FilterList(ruleconf);
+
+            // moderator bypass toggle - true by default, must be explicitly set to false
+            bool? bypass = ruleconf["AllowModBypass"]?.Value<bool>();
+            _modBypass = bypass.HasValue ? bypass.Value : true;
+
+            // embed matching mode
+            bool? embed = ruleconf["MatchEmbeds"]?.Value<bool>();
+            _embedMode = (embed.HasValue && embed == true);
+        }
+
+        /// <summary>
+        /// Checks given message to see if it matches this rule's constraints.
+        /// </summary>
+        /// <returns>If true, the rule's response(s) should be executed.</returns>
+        public bool Match(SocketMessage m, bool isMod)
+        {
+            // Regular or embed mode?
+            string msgcontent;
+            if (MatchEmbed) msgcontent = SerializeEmbed(m.Embeds);
+            else msgcontent = m.Content;
+
+            // Min/max length check
+            if (_msgMinLength != -1 && msgcontent.Length <= _msgMinLength) return false;
+            if (_msgMaxLength != -1 && msgcontent.Length >= _msgMaxLength) return false;
+
+            // Filter check
+            if (Filter.IsFiltered(m)) return false;
+            // Mod bypass check
+            if (AllowsModBypass && isMod) return false;
+
+            // Finally, regex checks
+            foreach (var regex in Regex)
+            {
+                if (regex.IsMatch(msgcontent)) return true;
+            }
+            return false;
+        }
+        
+        private string SerializeEmbed(IReadOnlyCollection<Embed> e)
+        {
+            var text = new StringBuilder();
+            foreach (var item in e) text.AppendLine(SerializeEmbed(item));
+            return text.ToString();
+        }
+
+        /// <summary>
+        /// Converts an embed to a plain string for easier matching.
+        /// </summary>
+        private string SerializeEmbed(Embed e)
+        {
+            StringBuilder result = new StringBuilder();
+            if (e.Author.HasValue) result.AppendLine(e.Author.Value.Name ?? "" + e.Author.Value.Url ?? "");
+
+            if (!string.IsNullOrWhiteSpace(e.Title)) result.AppendLine(e.Title);
+            if (!string.IsNullOrWhiteSpace(e.Description)) result.AppendLine(e.Description);
+
+            foreach (var f in e.Fields)
+            {
+                if (!string.IsNullOrWhiteSpace(f.Name)) result.AppendLine(f.Name);
+                if (!string.IsNullOrWhiteSpace(f.Value)) result.AppendLine(f.Value);
+            }
+
+            if (e.Footer.HasValue)
+            {
+                result.AppendLine(e.Footer.Value.Text ?? "");
+            }
+
+            return result.ToString();
+        }
+
+        public override string ToString() => $"Rule '{Label}'";
+    }
+}
diff --git a/RegexBot.cs b/RegexBot.cs
index 9ad5d9d..b093021 100644
--- a/RegexBot.cs
+++ b/RegexBot.cs
@@ -55,7 +55,8 @@ namespace Noikoio.RegexBot
                     arg.Message));
 
             // With features initialized, finish loading configuration
-            if (!_config.ReloadServerConfig().GetAwaiter().GetResult())
+            var conf = _config.ReloadServerConfig().Result;
+            if (conf == false)
             {
                 Console.WriteLine("Failed to load server configuration.");
 #if DEBUG