diff --git a/src/commands/clear.ts b/src/commands/clear.ts
new file mode 100644
index 0000000..e013359
--- /dev/null
+++ b/src/commands/clear.ts
@@ -0,0 +1,24 @@
+/**
+ * @copyright nhcarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import {
+  ApplicationIntegrationType,
+  SlashCommandBuilder,
+  InteractionContextType,
+} from "discord.js";
+
+const command = new SlashCommandBuilder().
+  setContexts(
+    InteractionContextType.BotDM,
+    InteractionContextType.Guild,
+    InteractionContextType.PrivateChannel,
+  ).
+  setIntegrationTypes(ApplicationIntegrationType.UserInstall).
+  setName("clear").
+  setDescription("Clear your current conversation so you can start a new one!");
+
+// eslint-disable-next-line no-console -- We don't need our logger here as this never runs in production.
+console.log(JSON.stringify(command.toJSON()));
diff --git a/src/events/message.ts b/src/events/message.ts
index 0caeb2c..303640e 100644
--- a/src/events/message.ts
+++ b/src/events/message.ts
@@ -14,13 +14,14 @@ import { personality } from "../config/personality.js";
 import { ai } from "../utils/ai.js";
 import { calculateCost } from "../utils/calculateCost.js";
 import { isSubscribedMessage } from "../utils/isSubscribed.js";
+import { logger } from "../utils/logger.js";
 import type { MessageParam } from "@anthropic-ai/sdk/resources/index.js";
 
 /**
  * Handles the Discord message event.
  * @param message - The message payload from Discord.
  */
-// eslint-disable-next-line max-lines-per-function -- We're off by one bloody line.
+// eslint-disable-next-line max-lines-per-function, max-statements -- We're off by one bloody line.
 export const onMessage = async(message: Message): Promise<void> => {
   try {
     if (message.channel.type !== ChannelType.DM) {
@@ -33,17 +34,29 @@ export const onMessage = async(message: Message): Promise<void> => {
     if (!subbed) {
       return;
     }
-    const history = await message.channel.messages.fetch({ limit: 6 });
-    const context: Array<MessageParam>
-    = history.reverse().map((messageInner) => {
-      return {
-        content: messageInner.content,
-        role:
-          messageInner.author.id === message.client.user.id
-            ? "assistant"
-            : "user",
-      };
+    const historyRequest = await message.channel.messages.fetch({ limit: 20 });
+    const history = [ ...historyRequest.values() ];
+    const clearMessageIndex = history.findIndex((messageInner) => {
+      return (
+        messageInner.content === "<Clear History>"
+        && messageInner.author.id === message.client.user.id
+      );
     });
+    if (clearMessageIndex !== -1) {
+      // Remove the clear message and everything sent before it, which means everything after in the array because the array is backwards
+      history.splice(clearMessageIndex, history.length - clearMessageIndex);
+    }
+    const context: Array<MessageParam> = history.
+      reverse().
+      map((messageInner) => {
+        return {
+          content: messageInner.content,
+          role:
+            messageInner.author.id === message.client.user.id
+              ? "assistant"
+              : "user",
+        };
+      });
     const messages = await ai.messages.create({
       // eslint-disable-next-line @typescript-eslint/naming-convention -- Required key format for SDK.
       max_tokens:  3000,
@@ -61,8 +74,13 @@ export const onMessage = async(message: Message): Promise<void> => {
       response?.text ?? "There was an error. Please try again later.",
     );
 
+    if (!response) {
+      await logger.log("info", `No response from AI, here's the payload: ${JSON.stringify(messages)}`);
+    }
+
     await calculateCost(messages.usage, message.author.username);
   } catch (error) {
+    await logger.error("message event", error as Error);
     const button = new ButtonBuilder().
       setLabel("Need help?").
       setStyle(ButtonStyle.Link).
diff --git a/src/index.ts b/src/index.ts
index d9df46e..ead2758 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -6,6 +6,7 @@
 import { Client, Events, GatewayIntentBits, Partials } from "discord.js";
 import { onMessage } from "./events/message.js";
 import { about } from "./modules/about.js";
+import { clear } from "./modules/clear.js";
 import { instantiateServer } from "./server/serve.js";
 import { logger } from "./utils/logger.js";
 
@@ -45,6 +46,9 @@ client.on(Events.InteractionCreate, (interaction) => {
           ephemeral: true,
         });
         break;
+      case "clear":
+        void clear(interaction);
+        break;
       default:
         void interaction.reply({
           content:   `I'm sorry, I don't know the ${interaction.commandName} command.`,
diff --git a/src/modules/clear.ts b/src/modules/clear.ts
new file mode 100644
index 0000000..8e7eb8b
--- /dev/null
+++ b/src/modules/clear.ts
@@ -0,0 +1,47 @@
+/**
+ * @copyright nhcarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import {
+  MessageFlags,
+  type ChatInputCommandInteraction,
+} from "discord.js";
+import { isSubscribedInteraction } from "../utils/isSubscribed.js";
+import { logger } from "../utils/logger.js";
+import { replyToError } from "../utils/replyToError.js";
+
+/**
+ * Sends a clear message in the DMs.
+ * @param interaction -- The interaction payload from Discord.
+ */
+export const clear = async(
+  interaction: ChatInputCommandInteraction,
+): Promise<void> => {
+  try {
+    await interaction.deferReply({ flags: [ MessageFlags.Ephemeral ] });
+
+    const subbed = await isSubscribedInteraction(interaction);
+    if (!subbed) {
+      return;
+    }
+    const sent = await interaction.user.send({
+      content: "<Clear History>",
+    }).catch(() => {
+      return null;
+    });
+
+    await interaction.editReply({
+      content: sent
+        ? "I have added a clear history marker to your DMs."
+        // eslint-disable-next-line stylistic/max-len -- This is a long string.
+        : "I was unable to send you a DM. Please ensure your privacy settings allow direct messages.",
+    });
+  } catch (error) {
+    await replyToError(interaction);
+    if (error instanceof Error) {
+      await logger.error("about command", error);
+    }
+  }
+};