diff --git a/src/structure/client/ModerationManager.js b/src/structure/client/ModerationManager.js
index 82c5bc3..4901df2 100644
--- a/src/structure/client/ModerationManager.js
+++ b/src/structure/client/ModerationManager.js
@@ -40,6 +40,22 @@ class ModerationManager {
 
     }
 
+    actions = {
+        prune: async (message, argument, targets) => {
+            const users = targets.map((t) => t.id);
+            let messages = await message.channel.messages.fetch({
+                limit: argument.value
+            });
+            messages = messages.filter((m) => {
+                return users.includes(m.author.id) && m.deletable;
+            });
+            try {
+                await message.channel.bulkDelete(messages, true);
+            } catch (err) { } //eslint-disable-line no-empty
+            return messages.size;
+        }
+    };
+
     async initialize() {
 
         //TODO: Load infractions for non-cached guilds...
@@ -189,7 +205,18 @@ class ModerationManager {
 
     }
 
-    async handleAutomod(Infraction, info) {
+    async handleAutomod(Infraction, target, info) {
+
+        const response = await this._handleTarget(Infraction, target, info);
+        const success = !response.error;
+
+        if (!success) {
+            this.client.emit('automodError', response);
+            return response;
+        }
+
+        if (info.prune) await this.actions.prune({ channel: info.channel }, { value: 100 }, [target]);
+        return response;
 
     }
 
@@ -310,27 +337,11 @@ class ModerationManager {
 
     async _handleArguments(message, targets) {
 
-        const actions = {
-            prune: async (message, argument, targets) => {
-                const users = targets.map((t) => t.id);
-                let messages = await message.channel.messages.fetch({
-                    limit: argument.value
-                });
-                messages = messages.filter((m) => {
-                    return users.includes(m.author.id) && m.deletable;
-                });
-                try {
-                    await message.channel.bulkDelete(messages, true);
-                } catch (err) { } //eslint-disable-line no-empty
-                return messages.size;
-            }
-        };
-
         const responses = {};
         for (const arg of Object.values(message.arguments)) {
             // console.log(arg, targets);
-            if (actions[arg.name]) {
-                const action = await actions[arg.name](message, arg, targets);
+            if (this.actions[arg.name]) {
+                const action = await this.actions[arg.name](message, arg, targets);
                 responses[arg.name] = action;
             }
         }
diff --git a/src/structure/components/observers/Automoderation.js b/src/structure/components/observers/Automoderation.js
index 1103a89..93d4f88 100644
--- a/src/structure/components/observers/Automoderation.js
+++ b/src/structure/components/observers/Automoderation.js
@@ -6,7 +6,6 @@ const { Observer } = require('../../interfaces');
 const { BinaryTree, Util, FilterUtil } = require('../../../utilities');
 const { FilterPresets } = require('../../../constants');
 const { Warn, Mute, Kick, Softban, Ban } = require('../infractions');
-const { GuildWrapper } = require('../../client/wrappers');
 
 const CONSTANTS = {
     Infractions: {
@@ -58,7 +57,7 @@ module.exports = class AutoModeration extends Observer {
         this.executing[filterResult.filter].push(member.id);
 
         const InfractionClass = CONSTANTS.Infractions[action.type];
-        const result = await this.client.moderationManager._handleTarget(InfractionClass, member, {
+        const result = await this.client.moderationManager.handleAutomod(InfractionClass, member, {
             wrapper,
             channel,
             executor: wrapper.guild.me,
@@ -66,15 +65,18 @@ module.exports = class AutoModeration extends Observer {
             duration: action.duration,
             points: action.points,
             expiration: action.expiration,
-            silent: true, //Won't DM Users.
+            silent: false, //Won't DM Users.
             force: false,
+            prune: action.prune,
             data: {
                 automoderation: filterResult
             }
         }).catch(this.logger.error.bind(this.logger));
+        filterResult.sanctioned = !result.error;
 
         await Util.wait(5000);
         this.executing[filterResult.filter].splice(this.executing[filterResult.filter].indexOf(member.id), 1);
+        return !result.error;
 
     }
 
@@ -261,12 +263,11 @@ module.exports = class AutoModeration extends Observer {
                 return this.client.rateLimiter.queueDelete(msg.channel, msg).catch(catcher(275));
             }
 
-            msg.filtered.sanctioned = true;
             this.client.rateLimiter.queueDelete(msg.channel, msg).catch(catcher(279));
             this.logger.debug(log + '\nSanctioned');
 
             filterResult.filter = 'word';
-            this._moderate(action, wrapper, channel, member, wrapper.format('W_FILTER_ACTION'), filterResult, message);
+            await this._moderate(action, wrapper, channel, member, wrapper.format('W_FILTER_ACTION'), filterResult, message);
 
         } else {
             this.client.rateLimiter.queueDelete(msg.channel, msg).catch(catcher(269));
@@ -331,6 +332,7 @@ module.exports = class AutoModeration extends Observer {
             }, [])
         };
 
+        // TODO: Add action buttons
         const sent = await logChannel.send({ embeds: [embed] }).catch((err) => {
             this.logger.error('Error in message flag:\n' + err.stack);
         });