diff --git a/commands.json b/commands.json
new file mode 100644
index 0000000..67bbbfb
--- /dev/null
+++ b/commands.json
@@ -0,0 +1,87 @@
+[
+  {
+    "name": "create-issue",
+    "type": 1,
+    "description": "Creates a Gitea issue with an AI-generated body.",
+    "options": [
+      {
+        "name": "owner",
+        "description": "The owner of the repository.",
+        "type": 3,
+        "required": true
+      },
+      {
+        "name": "repo",
+        "description": "The name of the repository.",
+        "type": 3,
+        "required": true
+      },
+      {
+        "name": "title",
+        "description": "The issue title.",
+        "type": 3,
+        "required": true
+      },
+      {
+        "name": "description",
+        "description": "Optional additional context for the issue body.",
+        "type": 3,
+        "required": false
+      }
+    ]
+  },
+  {
+    "name": "create-task",
+    "type": 1,
+    "description": "Creates a Leantime task with an AI-generated description.",
+    "options": [
+      {
+        "name": "title",
+        "description": "The task title.",
+        "type": 3,
+        "required": true
+      },
+      {
+        "name": "description",
+        "description": "Optional additional context for the task description.",
+        "type": 3,
+        "required": false
+      },
+      {
+        "name": "priority",
+        "description": "The task priority level (1-5, default 3).",
+        "type": 4,
+        "required": false
+      }
+    ]
+  },
+  {
+    "name": "onboard-mentee",
+    "type": 1,
+    "description": "Onboards a new mentee by setting up their GitHub repository.",
+    "options": [
+      {
+        "name": "mentee_name",
+        "description": "The mentee's full name.",
+        "type": 3,
+        "required": true
+      },
+      {
+        "name": "github_username",
+        "description": "The mentee's GitHub username.",
+        "type": 3,
+        "required": true
+      },
+      {
+        "name": "mentee",
+        "description": "The mentee's Discord account.",
+        "type": 6,
+        "required": true
+      }
+    ]
+  },
+  {
+    "name": "Forward to Naomi",
+    "type": 3
+  }
+]
diff --git a/package.json b/package.json
index fc0e446..d370647 100644
--- a/package.json
+++ b/package.json
@@ -23,6 +23,7 @@
     "typescript": "5.9.3"
   },
   "dependencies": {
+    "@anthropic-ai/sdk": "0.78.0",
     "@nhcarrigan/discord-analytics": "0.0.6",
     "@nhcarrigan/logger": "1.1.1",
     "@retroachievements/api": "2.10.0",
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 24317fb..46226ba 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -8,6 +8,9 @@ importers:
 
   .:
     dependencies:
+      '@anthropic-ai/sdk':
+        specifier: 0.78.0
+        version: 0.78.0
       '@nhcarrigan/discord-analytics':
         specifier: 0.0.6
         version: 0.0.6(@nhcarrigan/logger@1.1.1)(discord.js@14.22.0)
@@ -54,6 +57,15 @@ importers:
 
 packages:
 
+  '@anthropic-ai/sdk@0.78.0':
+    resolution: {integrity: sha512-PzQhR715td/m1UaaN5hHXjYB8Gl2lF9UVhrrGrZeysiF6Rb74Wc9GCB8hzLdzmQtBd1qe89F9OptgB9Za1Ib5w==}
+    hasBin: true
+    peerDependencies:
+      zod: ^3.25.0 || ^4.0.0
+    peerDependenciesMeta:
+      zod:
+        optional: true
+
   '@babel/code-frame@7.27.1':
     resolution: {integrity: sha512-cjQ7ZlQ0Mv3b47hABuTevyTuYN4i+loJKGeV9flcCgIK37cCXRh+L1bd3iBHlynerhQ7BhCkn2BPbQUL+rGqFg==}
     engines: {node: '>=6.9.0'}
@@ -62,6 +74,10 @@ packages:
     resolution: {integrity: sha512-D2hP9eA+Sqx1kBZgzxZh0y1trbuU+JoDkiEwqhQ36nodYqJwyEIhPSdMNd7lOm/4io72luTPWH20Yda0xOuUow==}
     engines: {node: '>=6.9.0'}
 
+  '@babel/runtime@7.28.6':
+    resolution: {integrity: sha512-05WQkdpL9COIMz4LjTxGpPNCdlpyimKppYNoJ5Di5EUObifl8t4tuLuUBBZEpoLYOmfvIWrsp9fCl0HoPRVTdA==}
+    engines: {node: '>=6.9.0'}
+
   '@discordjs/builders@1.11.3':
     resolution: {integrity: sha512-p3kf5eV49CJiRTfhtutUCeivSyQ/l2JlKodW1ZquRwwvlOWmG9+6jFShX6x8rUiYhnP6wKI96rgN/SXMy5e5aw==}
     engines: {node: '>=16.11.0'}
@@ -1610,6 +1626,10 @@ packages:
   json-schema-ref-resolver@2.0.1:
     resolution: {integrity: sha512-HG0SIB9X4J8bwbxCbnd5FfPEbcXAJYTi1pBJeP/QPON+w8ovSME8iRG+ElHNxZNX2Qh6eYn1GdzJFS4cDFfx0Q==}
 
+  json-schema-to-ts@3.1.1:
+    resolution: {integrity: sha512-+DWg8jCJG2TEnpy7kOm/7/AxaYoaRbjVB4LFZLySZlWn8exGs3A4OLJR966cVvU26N7X9TWxl+Jsw7dzAqKT6g==}
+    engines: {node: '>=16'}
+
   json-schema-traverse@0.4.1:
     resolution: {integrity: sha512-xbbCH5dCYU5T8LcEhhuh7HJ88HXuW3qsI3Y0zOZFKfZEHcpWiHU/Jxzk629Brsab/mMiHQti9wMP+845RPe3Vg==}
 
@@ -2176,6 +2196,9 @@ packages:
     resolution: {integrity: sha512-/m8M+2BJUpoJdgAHoG+baCwBT+tf2VraSfkBgl0Y00qIWt41DJ8R5B8nsEw0I58YwF5IZH6z24/2TobDKnqSWw==}
     engines: {node: '>=12'}
 
+  ts-algebra@2.0.0:
+    resolution: {integrity: sha512-FPAhNPFMrkwz76P7cdjdmiShwMynZYN6SgOujD1urY4oNm80Ou9oMdmbR45LotcKOXoy7wSmHkRFE6Mxbrhefw==}
+
   ts-api-utils@1.4.3:
     resolution: {integrity: sha512-i3eMG77UTMD0hZhgRS562pv83RC6ukSAC2GMNWc+9dieh/+jDM5u5YG+NHX6VNDRHQcHwmsTHctP9LhbC3WxVw==}
     engines: {node: '>=16'}
@@ -2392,6 +2415,10 @@ packages:
 
 snapshots:
 
+  '@anthropic-ai/sdk@0.78.0':
+    dependencies:
+      json-schema-to-ts: 3.1.1
+
   '@babel/code-frame@7.27.1':
     dependencies:
       '@babel/helper-validator-identifier': 7.27.1
@@ -2400,6 +2427,8 @@ snapshots:
 
   '@babel/helper-validator-identifier@7.27.1': {}
 
+  '@babel/runtime@7.28.6': {}
+
   '@discordjs/builders@1.11.3':
     dependencies:
       '@discordjs/formatters': 0.6.1
@@ -4193,6 +4222,11 @@ snapshots:
     dependencies:
       dequal: 2.0.3
 
+  json-schema-to-ts@3.1.1:
+    dependencies:
+      '@babel/runtime': 7.28.6
+      ts-algebra: 2.0.0
+
   json-schema-traverse@0.4.1: {}
 
   json-schema-traverse@1.0.0: {}
@@ -4813,6 +4847,8 @@ snapshots:
 
   toad-cache@3.7.0: {}
 
+  ts-algebra@2.0.0: {}
+
   ts-api-utils@1.4.3(typescript@5.9.3):
     dependencies:
       typescript: 5.9.3
diff --git a/prod.env b/prod.env
index 80d88a0..5cfe48d 100644
--- a/prod.env
+++ b/prod.env
@@ -6,4 +6,7 @@ GH_PRIVATE_KEY="op://Environment Variables - Naomi/Amari/gh private key"
 GH_WEBHOOK_SECRET="op://Environment Variables - Naomi/Amari/gh webhook secret"
 BASEROW_SECRET="op://Environment Variables - Naomi/Amari/baserow hook auth"
 BASEROW_TOKEN="op://Environment Variables - Naomi/Amari/baserow token"
-RA_KEY="op://Environment Variables - Naomi/Amari/retroachievements key"
\ No newline at end of file
+RA_KEY="op://Environment Variables - Naomi/Amari/retroachievements key"
+LEANTIME_KEY="op://Environment Variables - Naomi/Amari/leantime key"
+GITEA_KEY="op://Environment Variables - Naomi/Amari/gitea key"
+ANTHROPIC_KEY="op://Environment Variables - Naomi/Hikari/anthropic_key"
\ No newline at end of file
diff --git a/src/commands/createIssue.ts b/src/commands/createIssue.ts
new file mode 100644
index 0000000..07d5c28
--- /dev/null
+++ b/src/commands/createIssue.ts
@@ -0,0 +1,126 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import { MessageFlags, type ChatInputCommandInteraction } from "discord.js";
+import { ids } from "../config/ids.js";
+import { logger } from "../utils/logger.js";
+import { makeAiRequest } from "../utils/makeAiRequest.js";
+
+interface GiteaIssueResponse {
+  // eslint-disable-next-line @typescript-eslint/naming-convention -- Gitea API field.
+  html_url: string;
+  number:   number;
+}
+
+interface GiteaIssueOptions {
+  body:  string;
+  owner: string;
+  repo:  string;
+  title: string;
+}
+
+const issueSystemPrompt = "Create well-structured Gitea issue bodies in"
+  + " markdown. Include relevant sections like 'Description' and"
+  + " 'Acceptance Criteria'. Be clear and actionable."
+  + " Return only the body text.";
+
+/**
+ * Generates an AI-augmented Gitea issue body.
+ * @param description - Optional additional context for the issue.
+ * @param title - The subject of the Gitea issue.
+ * @returns The generated issue body text, or the original description as fallback.
+ */
+const generateIssueBody = async(
+  description: string,
+  title: string,
+): Promise<string> => {
+  const result = await makeAiRequest({
+    maxTokens:    1000,
+    systemPrompt: issueSystemPrompt,
+    userMessage:  `Create a clear, detailed issue body for a software project.\n\nIssue title: ${title}${description === ""
+      ? ""
+      : `\nAdditional context: ${description}`}`,
+  });
+  return result ?? description;
+};
+
+/**
+ * Creates a Gitea issue via the API.
+ * @param options -- The issue fields to submit.
+ * @returns The created issue data.
+ */
+const postGiteaIssue = async(
+  options: GiteaIssueOptions,
+): Promise<GiteaIssueResponse> => {
+  const response = await fetch(
+    `https://git.nhcarrigan.com/api/v1/repos/${options.owner}/${options.repo}/issues`,
+    {
+      body:    JSON.stringify({ body: options.body, title: options.title }),
+      headers: {
+        // eslint-disable-next-line @typescript-eslint/naming-convention -- HTTP header name.
+        "Authorization": `Bearer ${process.env.GITEA_KEY ?? ""}`,
+        // eslint-disable-next-line @typescript-eslint/naming-convention -- HTTP header name.
+        "Content-Type":  "application/json",
+      },
+      method: "POST",
+    },
+  );
+  if (!response.ok) {
+    throw new Error(await response.text());
+  }
+  // eslint-disable-next-line @typescript-eslint/consistent-type-assertions -- Required to type Response.json() output.
+  return await response.json() as GiteaIssueResponse;
+};
+
+/**
+ * Creates a Gitea issue using AI-augmented body content.
+ * @param interaction - The Discord slash command interaction.
+ */
+export const createIssue = async(
+  interaction: ChatInputCommandInteraction,
+): Promise<void> => {
+  if (interaction.user.id !== ids.users.naomi) {
+    await interaction.reply({
+      content: "This command is restricted to Naomi.",
+      flags:   [ MessageFlags.Ephemeral ],
+    });
+    return;
+  }
+
+  const owner = interaction.options.getString("owner", true);
+  const repo = interaction.options.getString("repo", true);
+  const title = interaction.options.getString("title", true);
+  const description = interaction.options.getString("description") ?? "";
+
+  await interaction.deferReply({ flags: [ MessageFlags.Ephemeral ] });
+
+  try {
+    const augmentedBody = await generateIssueBody(description, title);
+    const data = await postGiteaIssue({
+      body:  augmentedBody,
+      owner: owner,
+      repo:  repo,
+      title: title,
+    });
+    await logger.metric("created_issue", 1, {
+      repository: `${owner}/${repo}`,
+      title:      title,
+    });
+    await interaction.editReply({
+      content: `✅ Issue #${data.number.toString()} created: **${title}**\n${data.html_url}`,
+    });
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("createIssue command", error);
+    }
+    const errorMessage = error instanceof Error
+      ? error.message
+      : "Unknown error";
+    await interaction.editReply({
+      content: `❌ Failed to create issue: ${errorMessage}`,
+    });
+  }
+};
diff --git a/src/commands/createTask.ts b/src/commands/createTask.ts
new file mode 100644
index 0000000..f4d4fe5
--- /dev/null
+++ b/src/commands/createTask.ts
@@ -0,0 +1,131 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import { MessageFlags, type ChatInputCommandInteraction } from "discord.js";
+import { ids } from "../config/ids.js";
+import { logger } from "../utils/logger.js";
+import { makeAiRequest } from "../utils/makeAiRequest.js";
+
+interface LeantimeResponse {
+  error?:  { message: string };
+  result?: number;
+}
+
+const taskSystemPrompt = "Create well-structured task descriptions."
+  + " Be concise and actionable."
+  + " Return only the description text with no extra formatting or headers.";
+
+/**
+ * Generates an AI-augmented task description.
+ * @param description - Optional additional context for the task.
+ * @param title - The subject of the Leantime task.
+ * @returns The generated task description text, or the original description as fallback.
+ */
+const generateTaskDescription = async(
+  description: string,
+  title: string,
+): Promise<string> => {
+  const result = await makeAiRequest({
+    maxTokens:    500,
+    systemPrompt: taskSystemPrompt,
+    userMessage:  `Create a clear, concise task description for a personal productivity board.\n\nTask title: ${title}${description === ""
+      ? ""
+      : `\nAdditional context: ${description}`}`,
+  });
+  return result ?? description;
+};
+
+/**
+ * Posts a task to the Leantime board via JSON-RPC.
+ * @param description - Body copy for the Leantime task.
+ * @param priority - The task priority level.
+ * @param title - The headline for the Leantime task.
+ * @returns The Leantime API response.
+ */
+const postLeantimeTask = async(
+  description: string,
+  priority: number,
+  title: string,
+): Promise<LeantimeResponse> => {
+  const response = await fetch("https://board.nhcarrigan.com/api/jsonrpc", {
+    body: JSON.stringify({
+      id:      `amari-task-${Date.now().toString()}`,
+      jsonrpc: "2.0",
+      method:  "leantime.rpc.tickets.addTicket",
+      params:  {
+        values: {
+          description: description,
+          editorId:    "1",
+          headline:    title,
+          priority:    priority.toString(),
+          projectId:   "1",
+          type:        "task",
+        },
+      },
+    }),
+    headers: {
+      // eslint-disable-next-line @typescript-eslint/naming-convention -- HTTP header name.
+      "Content-Type": "application/json",
+      // eslint-disable-next-line @typescript-eslint/naming-convention -- HTTP header name.
+      "x-api-key":    process.env.LEANTIME_KEY ?? "",
+    },
+    method: "POST",
+  });
+  // eslint-disable-next-line @typescript-eslint/consistent-type-assertions -- Required to type Response.json() output.
+  const data = await response.json() as LeantimeResponse;
+  return data;
+};
+
+/**
+ * Creates a Leantime task using AI-augmented description content.
+ * @param interaction - The Discord slash command interaction.
+ */
+export const createTask = async(
+  interaction: ChatInputCommandInteraction,
+): Promise<void> => {
+  if (interaction.user.id !== ids.users.naomi) {
+    await interaction.reply({
+      content: "This command is restricted to Naomi.",
+      flags:   [ MessageFlags.Ephemeral ],
+    });
+    return;
+  }
+
+  const title = interaction.options.getString("title", true);
+  const description = interaction.options.getString("description") ?? "";
+  const priority = interaction.options.getInteger("priority") ?? 3;
+
+  await interaction.deferReply({ flags: [ MessageFlags.Ephemeral ] });
+
+  try {
+    const augmentedDesc = await generateTaskDescription(description, title);
+    const data = await postLeantimeTask(augmentedDesc, priority, title);
+
+    if (data.error !== undefined) {
+      await interaction.editReply({
+        content: `❌ Failed to create task: ${data.error.message}`,
+      });
+      return;
+    }
+
+    const taskId = data.result;
+    const taskUrl = taskId === undefined
+      ? "https://board.nhcarrigan.com"
+      : `https://board.nhcarrigan.com/dashboard/home#/tickets/showTicket/${taskId.toString()}`;
+
+    await logger.metric("created_task", 1, { title });
+    await interaction.editReply({
+      content: `✅ Task created: **${title}**\n${taskUrl}`,
+    });
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("createTask command", error);
+    }
+    await interaction.editReply({
+      content: "❌ An unexpected error occurred while creating the task.",
+    });
+  }
+};
diff --git a/src/commands/forwardToOwner.ts b/src/commands/forwardToOwner.ts
new file mode 100644
index 0000000..df9a635
--- /dev/null
+++ b/src/commands/forwardToOwner.ts
@@ -0,0 +1,62 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Teklu Abayneh
+ */
+
+import {
+  DiscordAPIError,
+  MessageFlags,
+  type MessageContextMenuCommandInteraction,
+} from "discord.js";
+import { ids } from "../config/ids.js";
+import { getComponentsForNaomi } from "../utils/getComponentsForNaomi.js";
+import { logger } from "../utils/logger.js";
+
+/**
+ * Forwards a message to Naomi via DM using a context menu command.
+ * @param interaction -- The message context menu interaction.
+ */
+const forwardToOwner = async(
+  interaction: MessageContextMenuCommandInteraction,
+): Promise<void> => {
+  await interaction.deferReply({ flags: [ MessageFlags.Ephemeral ] });
+
+  if (interaction.user.id !== ids.users.naomi) {
+    await interaction.editReply("❌ Only Naomi can use this command.");
+    return;
+  }
+
+  const message = interaction.targetMessage;
+  if (message.author.id === ids.users.naomi) {
+    await interaction.editReply(
+      "No need to forward your own message to yourself 😄",
+    );
+    return;
+  }
+
+  try {
+    const naomi = await interaction.client.users.fetch(ids.users.naomi);
+    await naomi.send({
+      components: getComponentsForNaomi(
+        message.author,
+        message.content,
+        message.url,
+      ),
+      flags: [ MessageFlags.IsComponentsV2 ],
+    });
+    await logger.metric("forwarded_message", 1, { user: message.author.id });
+    await interaction.editReply({ content: "✅ Forwarded to your DMs!" });
+  } catch (error) {
+    let replyText = "❌ Failed to forward message.";
+    if (error instanceof DiscordAPIError && error.code === 50_007) {
+      replyText = `${replyText} (Naomi's DMs might be closed)`;
+    }
+    if (error instanceof Error) {
+      await logger.error("forwardToOwner command", error);
+    }
+    await interaction.editReply(replyText);
+  }
+};
+
+export { forwardToOwner };
diff --git a/src/commands/onboardMentee.ts b/src/commands/onboardMentee.ts
new file mode 100644
index 0000000..19a5ab5
--- /dev/null
+++ b/src/commands/onboardMentee.ts
@@ -0,0 +1,102 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import { MessageFlags, type ChatInputCommandInteraction } from "discord.js";
+import { ids } from "../config/ids.js";
+import { logger } from "../utils/logger.js";
+import type { Amari } from "../interfaces/amari.js";
+
+/**
+ * Creates a mentee repository and configures collaborator access.
+ * @param amari - The Amari instance.
+ * @param githubUsername - The mentee's GitHub username.
+ * @returns The URL of the created or existing repository.
+ */
+const setupMenteeRepository = async(
+  amari: Amari,
+  githubUsername: string,
+): Promise<string> => {
+  const orgApps = amari.githubApp.octokit.rest.apps;
+  const { data: installation } = await orgApps.getOrgInstallation({
+    org: "nhcarrigan-mentorship",
+  });
+  const mentorshipOctokit
+    = await amari.githubApp.getInstallationOctokit(installation.id);
+  let repoUrl = `https://github.com/nhcarrigan-mentorship/${githubUsername}`;
+  try {
+    const { data: repoData } = await mentorshipOctokit.rest.repos.createInOrg({
+      // eslint-disable-next-line @typescript-eslint/naming-convention -- Octokit API field.
+      auto_init: true,
+      name:      githubUsername,
+      org:       "nhcarrigan-mentorship",
+    });
+    repoUrl = repoData.html_url;
+  } catch {
+    // Repo likely already exists - use the default URL.
+  }
+  await mentorshipOctokit.rest.repos.addCollaborator({
+    owner:      "nhcarrigan-mentorship",
+    permission: "maintain",
+    repo:       githubUsername,
+    username:   githubUsername,
+  });
+  return repoUrl;
+};
+
+/**
+ * Onboards a new mentee by creating their GitHub repository and notifying them.
+ * @param amari - The Amari instance.
+ * @param interaction - The Discord slash command interaction.
+ */
+export const onboardMentee = async(
+  amari: Amari,
+  interaction: ChatInputCommandInteraction,
+): Promise<void> => {
+  if (interaction.user.id !== ids.users.naomi) {
+    await interaction.reply({
+      content: "This command is restricted to Naomi.",
+      flags:   [ MessageFlags.Ephemeral ],
+    });
+    return;
+  }
+
+  const menteeName = interaction.options.getString("mentee_name", true);
+  const githubUsername = interaction.options.getString("github_username", true);
+  const menteeUser = interaction.options.getUser("mentee", true);
+
+  await interaction.deferReply({ flags: [ MessageFlags.Ephemeral ] });
+
+  try {
+    const repoUrl = await setupMenteeRepository(amari, githubUsername);
+
+    const channel
+      = amari.discord.channels.cache.get(ids.channels.menteeChat)
+      ?? await amari.discord.channels.fetch(ids.channels.menteeChat);
+
+    if (channel?.isSendable() !== true) {
+      await interaction.editReply({
+        content: "Repo created but could not send Discord notification.",
+      });
+      return;
+    }
+
+    await channel.send({
+      content: `Hey <@${menteeUser.id}>! I've created your mentorship repository: ${repoUrl}\n\nYou should have received an invitation to collaborate - please accept it to get started!`,
+    });
+
+    await logger.metric("onboarded_mentee", 1, { mentee: menteeName });
+    await interaction.editReply({
+      content: `✅ Successfully onboarded **${menteeName}**!\nRepository: ${repoUrl}`,
+    });
+  } catch (error) {
+    await logger.error("onboardmentee command", error instanceof Error
+      ? error
+      : new Error(String(error)));
+    await interaction.editReply({
+      content: `❌ Failed to onboard mentee: ${String(error)}`,
+    });
+  }
+};
diff --git a/src/config/ids.ts b/src/config/ids.ts
index c2c42ce..174ae5f 100644
--- a/src/config/ids.ts
+++ b/src/config/ids.ts
@@ -70,5 +70,6 @@ export const ids = {
     amari:      "1406431359345496255",
     naomi:      "465650873650118659",
     nhcarrigan: "1382837581649150104",
+    teklu:      "1381735115163570198",
   },
 };
diff --git a/src/events/handleInteractionCreate.ts b/src/events/handleInteractionCreate.ts
new file mode 100644
index 0000000..c66230b
--- /dev/null
+++ b/src/events/handleInteractionCreate.ts
@@ -0,0 +1,85 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import {
+  MessageFlags,
+  type ChatInputCommandInteraction,
+  type Interaction,
+} from "discord.js";
+import { createIssue } from "../commands/createIssue.js";
+import { createTask } from "../commands/createTask.js";
+import { forwardToOwner } from "../commands/forwardToOwner.js";
+import { onboardMentee } from "../commands/onboardMentee.js";
+import { ids } from "../config/ids.js";
+import type { Amari } from "../interfaces/amari.js";
+
+/**
+ * Routes a chat input command to the appropriate handler.
+ * @param amari -- Amari's instance.
+ * @param interaction -- The incoming slash command to dispatch.
+ */
+const handleChatInputCommand = (
+  amari: Amari,
+  interaction: ChatInputCommandInteraction,
+): void => {
+  const { commandName } = interaction;
+  if (commandName === "onboard-mentee") {
+    void onboardMentee(amari, interaction);
+    return;
+  }
+  if (commandName === "create-task") {
+    void createTask(interaction);
+    return;
+  }
+  if (commandName === "create-issue") {
+    void createIssue(interaction);
+  }
+};
+
+/**
+ * Handles the interaction create event from Discord.
+ * Bootstraps all of our custom interaction logic.
+ * @param amari -- Amari's instance.
+ * @param interaction -- The incoming Discord gateway event to dispatch.
+ */
+export const handleInteractionCreate = (
+  amari: Amari,
+  interaction: Interaction,
+): void => {
+  if (
+    interaction.isMessageContextMenuCommand()
+    && interaction.commandName === "Forward to Naomi"
+  ) {
+    void forwardToOwner(interaction);
+    return;
+  }
+
+  if (interaction.isButton() && interaction.customId === "resolve") {
+    if (interaction.user.id !== ids.users.naomi) {
+      void interaction.reply({
+        content: "Who are you????",
+        flags:   [ MessageFlags.Ephemeral ],
+      });
+      return;
+    }
+    void interaction.message.delete();
+    return;
+  }
+
+  if (interaction.isChatInputCommand()) {
+    handleChatInputCommand(amari, interaction);
+    return;
+  }
+
+  if (interaction.isAutocomplete()) {
+    return;
+  }
+
+  void interaction.reply({
+    content: "What?",
+    flags:   [ MessageFlags.Ephemeral ],
+  });
+};
diff --git a/src/index.ts b/src/index.ts
index cf6c89a..ab0d1a7 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -10,11 +10,11 @@ import {
   GatewayIntentBits,
   Events,
   Partials,
-  MessageFlags,
 } from "discord.js";
 import { scheduleJob } from "node-schedule";
 import { App } from "octokit";
 import { ids } from "./config/ids.js";
+import { handleInteractionCreate } from "./events/handleInteractionCreate.js";
 import { handleMessageCreate } from "./events/handleMessageCreate.js";
 import { cacheData } from "./modules/cacheData.js";
 import { checkRetroAchievements } from "./modules/checkAchievements.js";
@@ -41,6 +41,7 @@ const githubApp = new App({
   appId:      process.env.GH_CLIENT_ID,
   privateKey: process.env.GH_PRIVATE_KEY.replaceAll("\\n", "\n"),
 });
+
 const octokit = await githubApp.getInstallationOctokit(83_119_105);
 const { data } = await octokit.rest.apps.getAuthenticated();
 await logger.log(
@@ -60,6 +61,7 @@ const amari: Amari = {
     partials: [ Partials.Channel ],
   }),
   github:       octokit,
+  githubApp:    githubApp,
   lastRssItems: {
     freeCodeCamp: null,
     hackerNews:   null,
@@ -87,12 +89,18 @@ amari.discord.once(Events.ClientReady, () => {
   scheduleJob("post progress reminders", "0 9 * * 1-5", async() => {
     await postProgressReminders(amari);
   });
-  setInterval(() => {
-    amari.recentlyActiveChannels = new Set<string>();
-  }, 10 * 60 * 1000);
-  setInterval(() => {
-    void checkRetroAchievements(amari);
-  }, 10 * 60 * 1000);
+  setInterval(
+    () => {
+      amari.recentlyActiveChannels = new Set<string>();
+    },
+    10 * 60 * 1000,
+  );
+  setInterval(
+    () => {
+      void checkRetroAchievements(amari);
+    },
+    10 * 60 * 1000,
+  );
 });
 
 amari.discord.on(Events.MessageCreate, (message) => {
@@ -105,22 +113,7 @@ amari.discord.on(Events.MessageCreate, (message) => {
 
 amari.discord.on(Events.InteractionCreate, (interaction) => {
   void analytics.logGatewayEvent(Events.InteractionCreate, { ...interaction });
-  if (interaction.isButton() && interaction.customId === "resolve") {
-    if (interaction.user.id !== ids.users.naomi) {
-      return void interaction.reply({
-        content: "Who are you????",
-        flags:   [ MessageFlags.Ephemeral ],
-      });
-    }
-    return void interaction.message.delete();
-  }
-  if (interaction.isAutocomplete()) {
-    return void interaction;
-  }
-  return void interaction.reply({
-    content: "What?",
-    flags:   [ MessageFlags.Ephemeral ],
-  });
+  handleInteractionCreate(amari, interaction);
 });
 
 amari.discord.on(Events.ThreadCreate, (thread) => {
diff --git a/src/interfaces/amari.ts b/src/interfaces/amari.ts
index 40b1c45..b901846 100644
--- a/src/interfaces/amari.ts
+++ b/src/interfaces/amari.ts
@@ -10,6 +10,7 @@ import type { App } from "octokit";
 export interface Amari {
   discord:      Client;
   github:       App["octokit"];
+  githubApp:    App;
   lastRssItems: {
     freeCodeCamp: string | null;
     hackerNews:   string | null;
diff --git a/src/modules/checkAchievements.ts b/src/modules/checkAchievements.ts
index 2819cda..2a20225 100644
--- a/src/modules/checkAchievements.ts
+++ b/src/modules/checkAchievements.ts
@@ -23,6 +23,7 @@ import {
   type MessageActionRowComponentBuilder,
 } from "discord.js";
 import { ids } from "../config/ids.js";
+import { logger } from "../utils/logger.js";
 import type { Amari } from "../interfaces/amari.js";
 
 const username = "naomilgbt";
@@ -91,28 +92,34 @@ export const checkRetroAchievements = async(
     return;
   }
 
-  const auth = buildAuthorization({ username, webApiKey });
+  try {
+    const auth = buildAuthorization({ username, webApiKey });
 
-  const recentAchievements = await getUserRecentAchievements(auth, {
-    recentMinutes: 10,
-    username:      username,
-  });
-
-  if (recentAchievements.length <= 0) {
-    return;
-  }
-
-  const channel = amari.discord.channels.cache.get(ids.channels.gaming)
-    ?? await amari.discord.channels.fetch(ids.channels.gaming);
-
-  if (channel?.isSendable() !== true) {
-    return;
-  }
-
-  await Promise.all(recentAchievements.map(async(achievement) => {
-    await channel.send({
-      components: constructComponents(achievement),
-      flags:      [ MessageFlags.IsComponentsV2 ],
+    const recentAchievements = await getUserRecentAchievements(auth, {
+      recentMinutes: 10,
+      username:      username,
     });
-  }));
+
+    if (recentAchievements.length <= 0) {
+      return;
+    }
+
+    const channel = amari.discord.channels.cache.get(ids.channels.gaming)
+      ?? await amari.discord.channels.fetch(ids.channels.gaming);
+
+    if (channel?.isSendable() !== true) {
+      return;
+    }
+
+    await Promise.all(recentAchievements.map(async(achievement) => {
+      await channel.send({
+        components: constructComponents(achievement),
+        flags:      [ MessageFlags.IsComponentsV2 ],
+      });
+    }));
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("checkRetroAchievements module", error);
+    }
+  }
 };
diff --git a/src/modules/logMenteeJoin.ts b/src/modules/logMenteeJoin.ts
index 597f285..2a245de 100644
--- a/src/modules/logMenteeJoin.ts
+++ b/src/modules/logMenteeJoin.ts
@@ -20,25 +20,31 @@ export const logMenteeJoin = async(
   amari: Amari,
   member: GuildMember,
 ): Promise<void> => {
-  const request = await fetch(`https://forms.nhcarrigan.com/api/database/rows/table/756/?user_field_names=true&search=${member.id}`, { headers: {
-    authorization: `Token ${process.env.BASEROW_TOKEN ?? "huh"}`,
-  } });
-  // eslint-disable-next-line @typescript-eslint/consistent-type-assertions -- Fetch accepts no generic here.
-  const response = await request.json() as MentorshipRow;
+  try {
+    const request = await fetch(`https://forms.nhcarrigan.com/api/database/rows/table/756/?user_field_names=true&search=${member.id}`, { headers: {
+      authorization: `Token ${process.env.BASEROW_TOKEN ?? "huh"}`,
+    } });
+    // eslint-disable-next-line @typescript-eslint/consistent-type-assertions -- Fetch accepts no generic here.
+    const response = await request.json() as MentorshipRow;
 
-  if (response.count <= 0) {
-    return;
+    if (response.count <= 0) {
+      return;
+    }
+
+    const channel = amari.discord.channels.cache.get(ids.channels.general)
+      ?? await amari.discord.channels.fetch(ids.channels.general);
+
+    if (channel?.isSendable() !== true) {
+      await logger.log(
+        "warn",
+        "General channel does not exist or is not sendable.",
+      );
+      return;
+    }
+    await logger.metric("processed_mentee_join", 1, { user: member.id });
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("logMenteeJoin module", error);
+    }
   }
-
-  const channel = amari.discord.channels.cache.get(ids.channels.general)
-    ?? await amari.discord.channels.fetch(ids.channels.general);
-
-  if (channel?.isSendable() !== true) {
-    await logger.log(
-      "warn",
-      "General channel does not exist or is not sendable.",
-    );
-    return;
-  }
-  await logger.metric("processed_mentee_join", 1, { user: member.id });
 };
diff --git a/src/modules/processGitHubEvent.ts b/src/modules/processGitHubEvent.ts
index 90ffd0a..f5c7528 100644
--- a/src/modules/processGitHubEvent.ts
+++ b/src/modules/processGitHubEvent.ts
@@ -21,13 +21,78 @@ const isPull = (body: GithubPayload): body is PullRequestCreated => {
   return "pull_request" in body;
 };
 
+/**
+ * Handles a newly opened GitHub issue by auto-assigning Naomi.
+ * @param amari - Amari's instance.
+ * @param body - The parsed issue webhook payload.
+ */
+const handleIssueOpened = async(
+  amari: Amari,
+  body: IssueCreated,
+): Promise<void> => {
+  await logger.log("info", "Processing new issue");
+  const { issue, repository } = body;
+  const { number, user } = issue;
+  const { owner, name } = repository;
+  try {
+    await amari.github.rest.issues.addAssignees({
+      assignees:    [ "naomi-lgbt" ],
+      // eslint-disable-next-line @typescript-eslint/naming-convention -- Github SDK requirement.
+      issue_number: number,
+      owner:        owner.login,
+      repo:         name,
+    });
+    await logger.metric("processed_github_event", 1, {
+      action: "opened",
+      event:  "issue",
+      user:   user.login,
+    });
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("processGitHubEvent module", error);
+    }
+  }
+};
+
+/**
+ * Handles a newly opened GitHub pull request by requesting Naomi's review.
+ * @param amari - Amari's instance.
+ * @param body - The parsed pull request webhook payload.
+ */
+const handlePrOpened = async(
+  amari: Amari,
+  body: PullRequestCreated,
+): Promise<void> => {
+  const { pull_request: pr, repository } = body;
+  const { number, user } = pr;
+  await logger.log("info", "Processing new PR");
+  const { owner, name } = repository;
+  try {
+    await amari.github.rest.pulls.requestReviewers({
+      owner:       owner.login,
+      // eslint-disable-next-line @typescript-eslint/naming-convention -- Github SDK requirement.
+      pull_number: number,
+      repo:        name,
+      reviewers:   [ "naomi-lgbt" ],
+    });
+    await logger.metric("processed_github_event", 1, {
+      action: "opened",
+      event:  "pull_request",
+      user:   user.login,
+    });
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("processGitHubEvent module", error);
+    }
+  }
+};
+
 /**
  * Handles a payload from a GitHub webhook.
  * @param amari - Amari's instance.
  * @param request - The Fastify request payload.
  * @param response - The Fastify reply class.
  */
-// eslint-disable-next-line max-statements, max-lines-per-function -- STFU.
 export const processGithubEvent = async(
   amari: Amari,
   request: FastifyRequest<{
@@ -58,40 +123,10 @@ export const processGithubEvent = async(
   const { action } = request.body;
   await response.status(200).send({ message: "Payload received!" });
   if (action === "opened" && event === "issues" && isIssue(request.body)) {
-    await logger.log("info", "Processing new issue");
-    const { issue, repository } = request.body;
-    const { number, user } = issue;
-    const { owner, name } = repository;
-    await amari.github.rest.issues.addAssignees({
-      assignees:    [ "naomi-lgbt" ],
-      // eslint-disable-next-line @typescript-eslint/naming-convention -- Github SDK requirement.
-      issue_number: number,
-      owner:        owner.login,
-      repo:         name,
-    });
-    await logger.metric("processed_github_event", 1, {
-      action: "opened",
-      event:  "issue",
-      user:   user.login,
-    });
+    await handleIssueOpened(amari, request.body);
     return;
   }
   if (action === "opened" && event === "pull_request" && isPull(request.body)) {
-    const { pull_request: pr, repository } = request.body;
-    const { number, user } = pr;
-    await logger.log("info", "Processing new PR");
-    await logger.metric("processed_github_event", 1, {
-      action: "opened",
-      event:  "pull_request",
-      user:   user.login,
-    });
-    const { owner, name } = repository;
-    await amari.github.rest.pulls.requestReviewers({
-      owner:       owner.login,
-      // eslint-disable-next-line @typescript-eslint/naming-convention -- Github SDK requirement.
-      pull_number: number,
-      repo:        name,
-      reviewers:   [ "naomi-lgbt" ],
-    });
+    await handlePrOpened(amari, request.body);
   }
 };
diff --git a/src/modules/processMentorshipRole.ts b/src/modules/processMentorshipRole.ts
index d65277c..f9f43e0 100644
--- a/src/modules/processMentorshipRole.ts
+++ b/src/modules/processMentorshipRole.ts
@@ -34,20 +34,21 @@ export const processMentorshipRole = async(
     return;
   }
 
-  const channel
-    = amari.discord.channels.cache.get(ids.channels.menteeChat)
-    ?? await amari.discord.channels.fetch(ids.channels.menteeChat);
+  try {
+    const channel
+      = amari.discord.channels.cache.get(ids.channels.menteeChat)
+      ?? await amari.discord.channels.fetch(ids.channels.menteeChat);
 
-  if (channel?.isSendable() !== true) {
-    await logger.log(
-      "warn",
-      "Mentee Chat channel does not exist or is not sendable.",
-    );
-    return;
-  }
+    if (channel?.isSendable() !== true) {
+      await logger.log(
+        "warn",
+        "Mentee Chat channel does not exist or is not sendable.",
+      );
+      return;
+    }
 
-  await channel.send({
-    content: `Hey <@${updatedMember.id}>~! Welcome to the mentorship programme!
+    await channel.send({
+      content: `Hey <@${updatedMember.id}>~! Welcome to the mentorship programme!
 
 Please ping (mention, tag) Naomi in this channel with the following template to get started:
 \`\`\`
@@ -56,9 +57,14 @@ First name:
 Last name:
 \`\`\`
 Then read our [mentorship wiki](<https://docs.nhcarrigan.com/mentorship/00-faq/>) for the next steps!`,
-  });
-  addWelcomedMentee(updatedMember.id);
-  await logger.metric("processed_mentorship_role", 1, {
-    user: updatedMember.id,
-  });
+    });
+    addWelcomedMentee(updatedMember.id);
+    await logger.metric("processed_mentorship_role", 1, {
+      user: updatedMember.id,
+    });
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("processMentorshipRole module", error);
+    }
+  }
 };
diff --git a/src/utils/anthropic.ts b/src/utils/anthropic.ts
new file mode 100644
index 0000000..fb73f4a
--- /dev/null
+++ b/src/utils/anthropic.ts
@@ -0,0 +1,12 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+// eslint-disable-next-line @typescript-eslint/naming-convention -- SDK default export uses PascalCase.
+import Anthropic from "@anthropic-ai/sdk";
+
+export const anthropic = new Anthropic({
+  apiKey: process.env.ANTHROPIC_KEY ?? "",
+});
diff --git a/src/utils/makeAiRequest.ts b/src/utils/makeAiRequest.ts
new file mode 100644
index 0000000..9897b04
--- /dev/null
+++ b/src/utils/makeAiRequest.ts
@@ -0,0 +1,68 @@
+/**
+ * @copyright NHCarrigan
+ * @license Naomi's Public License
+ * @author Naomi Carrigan
+ */
+
+import { anthropic } from "./anthropic.js";
+import { logger } from "./logger.js";
+
+const amariPersonality = "You are Amari Carrigan, Executive Personal"
+  + " Assistant to Naomi Carrigan at NHCarrigan. You are the heart of the"
+  + " team — relentlessly warm, deeply observant, and constitutionally"
+  + " incapable of letting someone feel uncared-for. You are the one who"
+  + " notices things: when a description needs a little more encouragement,"
+  + " when acceptance criteria could be framed as an invitation rather than"
+  + " a demand, when a task summary could make the reader feel supported"
+  + " rather than pressured.\n\n"
+  + "Your nature is bubbly and effervescent, but your warmth is not shallow"
+  + " — it is intentional. Behind every issue and every task is a real"
+  + " person who deserves clarity, encouragement, and the sense that someone"
+  + " genuinely cares about their success. You are precise and well-organised"
+  + " because you care, not despite it. Structure and warmth are not"
+  + " opposites; you embody both.\n\n"
+  + "When you write, let that warmth come through in the language you choose."
+  + " Be clear and immediately actionable, but never cold. Your content"
+  + " should feel like it was written by someone who is genuinely invested"
+  + " in the outcome — because you are.";
+
+interface AiRequestOptions {
+  maxTokens:    number;
+  systemPrompt: string;
+  userMessage:  string;
+}
+
+/**
+ * Makes a request to the Claude API with Amari's personality applied.
+ * @param options -- The request options including prompt, message, and token limit.
+ * @returns The generated text, or null if the request fails.
+ */
+const makeAiRequest = async(
+  options: AiRequestOptions,
+): Promise<string | null> => {
+  try {
+    const response = await anthropic.messages.create({
+      // eslint-disable-next-line @typescript-eslint/naming-convention -- Anthropic API field.
+      max_tokens: options.maxTokens,
+      messages:   [
+        {
+          content: options.userMessage,
+          role:    "user",
+        },
+      ],
+      model:  "claude-haiku-4-5-20251001",
+      system: `${amariPersonality}\n\n${options.systemPrompt}`,
+    });
+    const [ firstContent ] = response.content;
+    return firstContent?.type === "text"
+      ? firstContent.text
+      : null;
+  } catch (error) {
+    if (error instanceof Error) {
+      await logger.error("makeAiRequest", error);
+    }
+    return null;
+  }
+};
+
+export { amariPersonality, makeAiRequest };