diff --git a/apps/web/__tests__/ai-find-snippets.test.ts b/apps/web/__tests__/ai-find-snippets.test.ts
new file mode 100644
index 0000000000..ad41b9ee5f
--- /dev/null
+++ b/apps/web/__tests__/ai-find-snippets.test.ts
@@ -0,0 +1,91 @@
+import { describe, expect, test, vi } from "vitest";
+import { aiFindSnippets } from "@/utils/ai/snippets/find-snippets";
+import type { EmailForLLM } from "@/utils/ai/choose-rule/stringify-email";
+
+// pnpm test ai-find-snippets
+
+vi.mock("server-only", () => ({}));
+
+describe("aiFindSnippets", () => {
+  test("should find snippets in similar emails", async () => {
+    const emails = [
+      getEmail({
+        content:
+          "You can schedule a meeting with me here: https://cal.com/john-smith",
+      }),
+      getEmail({
+        content:
+          "Let's find a time to discuss. You can book a slot at https://cal.com/john-smith",
+      }),
+      getEmail({
+        content:
+          "Thanks for reaching out. Feel free to schedule a meeting at https://cal.com/john-smith",
+      }),
+    ];
+
+    const result = await aiFindSnippets({
+      sentEmails: emails,
+      user: getUser(),
+    });
+
+    expect(result.snippets).toHaveLength(1);
+    expect(result.snippets[0]).toMatchObject({
+      text: expect.stringContaining("cal.com/john-smith"),
+      count: 3,
+    });
+
+    console.log("Returned snippet:");
+    console.log(result.snippets[0]);
+  });
+
+  test("should return empty array for unique emails", async () => {
+    const emails = [
+      getEmail({
+        content:
+          "Hi Sarah, Thanks for the update on Project Alpha. I've reviewed the latest metrics and everything looks on track. Could you share the Q2 projections when you have a moment? Best, Alex",
+      }),
+      getEmail({
+        content:
+          "Just wanted to follow up on the marketing campaign results. The conversion rates are looking promising, but we should discuss optimizing the landing page. Let me know when you're free to chat. Thanks, Alex",
+      }),
+      getEmail({
+        content:
+          "Thanks for looping me in on the client feedback. I'll review the suggestions and share my thoughts during tomorrow's standup. Looking forward to moving this forward. Best regards, Alex",
+      }),
+    ];
+
+    const result = await aiFindSnippets({
+      sentEmails: emails,
+      user: getUser(),
+    });
+
+    expect(result.snippets).toHaveLength(0);
+  });
+});
+
+// helpers
+function getEmail({
+  from = "user@test.com",
+  subject = "Test Subject",
+  content = "Test content",
+  replyTo,
+  cc,
+}: Partial<EmailForLLM> = {}): EmailForLLM {
+  return {
+    from,
+    subject,
+    content,
+    ...(replyTo && { replyTo }),
+    ...(cc && { cc }),
+  };
+}
+
+function getUser() {
+  return {
+    aiModel: null,
+    aiProvider: null,
+    email: "user@test.com",
+    aiApiKey: null,
+    about: null,
+  };
+}
diff --git a/apps/web/app/api/user/bulk-archive/route.ts b/apps/web/app/api/user/bulk-archive/route.ts
index 51ccd89597..f92ddc49bd 100644
--- a/apps/web/app/api/user/bulk-archive/route.ts
+++ b/apps/web/app/api/user/bulk-archive/route.ts
@@ -3,7 +3,12 @@ import { NextResponse } from "next/server";
 import type { gmail_v1 } from "@googleapis/gmail";
 import { auth } from "@/app/api/auth/[...nextauth]/auth";
 import { getGmailClient } from "@/utils/gmail/client";
-import { INBOX_LABEL_ID, getOrCreateInboxZeroLabel } from "@/utils/gmail/label";
+import {
+  INBOX_LABEL_ID,
+  getOrCreateInboxZeroLabel,
+  labelVisibility,
+  messageVisibility,
+} from "@/utils/gmail/label";
 import { sleep } from "@/utils/sleep";
 import { withError } from "@/utils/middleware";
 
@@ -24,8 +29,8 @@ async function bulkArchive(body: BulkArchiveBody, gmail: gmail_v1.Gmail) {
   const archivedLabel = await getOrCreateInboxZeroLabel({
     gmail,
     key: "archived",
-    messageListVisibility: "hide",
-    labelListVisibility: "labelHide",
+    messageListVisibility: messageVisibility.hide,
+    labelListVisibility: labelVisibility.labelHide,
   });
 
   if (!archivedLabel.id)
diff --git a/apps/web/utils/actions/ai-rule.ts b/apps/web/utils/actions/ai-rule.ts
index 634901c076..14779a1431 100644
--- a/apps/web/utils/actions/ai-rule.ts
+++ b/apps/web/utils/actions/ai-rule.ts
@@ -36,9 +36,10 @@ import { aiPromptToRules } from "@/utils/ai/rule/prompt-to-rules";
 import { aiDiffRules } from "@/utils/ai/rule/diff-rules";
 import { aiFindExistingRules } from "@/utils/ai/rule/find-existing-rules";
 import { aiGenerateRulesPrompt } from "@/utils/ai/rule/generate-rules-prompt";
-import { getLabels } from "@/utils/gmail/label";
+import { getLabelById, getLabels, labelVisibility } from "@/utils/gmail/label";
 import { withActionInstrumentation } from "@/utils/actions/middleware";
 import { createScopedLogger } from "@/utils/logger";
+import { aiFindSnippets } from "@/utils/ai/snippets/find-snippets";
 
 const logger = createScopedLogger("ai-rule");
 
@@ -766,7 +767,13 @@ export const generateRulesPromptAction = withActionInstrumentation(
 
     const user = await prisma.user.findUnique({
       where: { id: session.user.id },
-      select: { aiProvider: true, aiModel: true, aiApiKey: true, email: true },
+      select: {
+        aiProvider: true,
+        aiModel: true,
+        aiApiKey: true,
+        email: true,
+        about: true,
+      },
     });
 
     if (!user) return { error: "User not found" };
@@ -775,10 +782,25 @@ export const generateRulesPromptAction = withActionInstrumentation(
     const gmail = getGmailClient(session);
     const lastSent = await getMessages(gmail, {
       query: "in:sent",
-      maxResults: 20,
+      maxResults: 50,
     });
     const gmailLabels = await getLabels(gmail);
     const userLabels = gmailLabels?.filter((label) => label.type === "user");
+
+    const labelsWithCounts: { label: string; threadsTotal: number }[] = [];
+
+    for (const label of userLabels || []) {
+      if (!label.id) continue;
+      if (label.labelListVisibility === labelVisibility.labelHide) continue;
+      const labelById = await getLabelById({ gmail, id: label.id });
+      if (!labelById?.name) continue;
+      if (!labelById.threadsTotal) continue; // Skip labels with 0 threads
+      labelsWithCounts.push({
+        label: labelById.name,
+        threadsTotal: labelById.threadsTotal || 0,
+      });
+    }
+
     const lastSentMessages = (
       await Promise.all(
         lastSent.messages?.map(async (message) => {
@@ -799,11 +821,26 @@ export const generateRulesPromptAction = withActionInstrumentation(
       );
     });
 
+    const snippetsResult = await aiFindSnippets({
+      user,
+      sentEmails: lastSentMessages.map((message) => ({
+        from: message.headers.from,
+        replyTo: message.headers["reply-to"],
+        cc: message.headers.cc,
+        subject: message.headers.subject,
+        content: emailToContent({
+          textHtml: message.textHtml || null,
+          textPlain: message.textPlain || null,
+          snippet: message.snippet,
+        }),
+      })),
+    });
+
     const result = await aiGenerateRulesPrompt({
-      user: { ...user, email: user.email },
+      user,
       lastSentEmails,
-      userLabels:
-        userLabels?.map((label) => label.name).filter(isDefined) || [],
+      snippets: snippetsResult.snippets.map((snippet) => snippet.text),
+      userLabels: labelsWithCounts.map((label) => label.label),
     });
 
     if (isActionError(result)) return { error: result.error };
diff --git a/apps/web/utils/ai/choose-rule/execute.ts b/apps/web/utils/ai/choose-rule/execute.ts
index 70b011ebb7..1da343377f 100644
--- a/apps/web/utils/ai/choose-rule/execute.ts
+++ b/apps/web/utils/ai/choose-rule/execute.ts
@@ -2,7 +2,12 @@ import type { gmail_v1 } from "@googleapis/gmail";
 import { type EmailForAction, runActionFunction } from "@/utils/ai/actions";
 import prisma from "@/utils/prisma";
 import type { Prisma } from "@prisma/client";
-import { getOrCreateInboxZeroLabel, labelThread } from "@/utils/gmail/label";
+import {
+  getOrCreateInboxZeroLabel,
+  labelThread,
+  labelVisibility,
+  messageVisibility,
+} from "@/utils/gmail/label";
 import { ExecutedRuleStatus } from "@prisma/client";
 import { createScopedLogger } from "@/utils/logger";
 
@@ -30,8 +35,8 @@ export async function executeAct({
     const label = await getOrCreateInboxZeroLabel({
       gmail,
       key: "acted",
-      messageListVisibility: "hide",
-      labelListVisibility: "labelHide",
+      messageListVisibility: messageVisibility.hide,
+      labelListVisibility: labelVisibility.labelHide,
     });
 
     if (!label.id) return;
diff --git a/apps/web/utils/ai/rule/generate-rules-prompt.ts b/apps/web/utils/ai/rule/generate-rules-prompt.ts
index b924850c51..60fe1d9d17 100644
--- a/apps/web/utils/ai/rule/generate-rules-prompt.ts
+++ b/apps/web/utils/ai/rule/generate-rules-prompt.ts
@@ -1,6 +1,10 @@
 import { z } from "zod";
 import { chatCompletionTools } from "@/utils/llms";
 import type { UserAIFields } from "@/utils/llms/types";
+import type { User } from "@prisma/client";
+import { createScopedLogger } from "@/utils/logger";
+
+const logger = createScopedLogger("ai-generate-rules-prompt");
 
 const parameters = z.object({
   rules: z
@@ -8,45 +12,82 @@ const parameters = z.object({
     .describe("List of generated rules for email management"),
 });
 
+const parametersSnippets = z.object({
+  rules: z
+    .array(
+      z.object({
+        rule: z.string().describe("The rule to apply to the email"),
+        snippet: z
+          .string()
+          .optional()
+          .describe(
+            "Optional: Include ONLY if this is a snippet-based rule. The exact snippet text this rule is based on.",
+          ),
+      }),
+    )
+    .describe("List of generated rules for email management"),
+});
+
 export async function aiGenerateRulesPrompt({
   user,
   lastSentEmails,
+  snippets,
   userLabels,
 }: {
-  user: UserAIFields & { email: string };
+  user: UserAIFields & Pick<User, "email" | "about">;
   lastSentEmails: string[];
   userLabels: string[];
+  snippets: string[];
 }): Promise<string[]> {
-  const emailSummary = lastSentEmails
-    .map((email, index) => `Email ${index + 1}:\n${email}\n`)
-    .join("\n");
-
   const labelsList = userLabels
-    ? userLabels.map((label) => `- ${label}`).join("\n")
+    ? userLabels
+        .map((label) => `<label><name>${label}</name></label>`)
+        .join("\n")
     : "No labels found";
 
-  const system =
-    "You are an AI assistant that helps people manage their emails by generating rules based on their email behavior and existing labels.";
-
-  const prompt = `
-Analyze the user's email behavior and suggest general rules for managing their inbox effectively. Here's the context:
+  const hasSnippets = snippets.length > 0;
 
-User Email: ${user.email}
+  // When using snippets, we show fewer emails to the AI to avoid overwhelming it
+  const lastSentEmailsCount = hasSnippets ? 20 : 50;
 
-Last 20 Sent Emails:
-${emailSummary}
+  const system =
+    "You are an AI assistant that helps people manage their emails by generating rules based on their email behavior and existing labels.";
 
-User's Labels:
+  const prompt = `Analyze the user's email behavior and suggest general rules for managing their inbox effectively. Here's the context:
+
+<user_email>
+${user.email}
+</user_email>
+${user.about ? `\n<about_user>\n${user.about}\n</about_user>\n` : ""}
+<last_sent_emails>
+${lastSentEmails
+  .slice(0, lastSentEmailsCount)
+  .map((email) => `<email>\n${email}\n</email>`)
+  .join("\n")}
+</last_sent_emails>
+${
+  hasSnippets
+    ? `<user_snippets>\n${snippets
+        .map((snippet) => `<snippet>\n${snippet}\n</snippet>`)
+        .join("\n")}\n</user_snippets>`
+    : ""
+}
+<user_labels>
 ${labelsList}
+</user_labels>
 
-Generate a list of email management rules that would be broadly applicable for this user based on their email behavior and existing labels. The rules should be general enough to apply to various situations, not just specific recent emails. Include actions such as labeling, archiving, forwarding, replying, and drafting responses. Here are some examples of the format and complexity of rules you can create:
+<instructions>
+Generate a list of email management rules that would be broadly applicable for this user based on their email behavior and existing labels. The rules should be general enough to apply to various situations, not just specific recent emails. Include actions such as labeling, archiving, forwarding, replying, and drafting responses.
+</instructions>
 
+<example_rules>
 * Label newsletters as "Newsletter" and archive them
 * If someone asks to schedule a meeting, send them your calendar link
 * For cold emails or unsolicited pitches, draft a polite decline response
 * Label emails related to financial matters as "Finance" and mark as important
 * Forward emails about technical issues to the support team
 * For emails from key clients or partners, label as "VIP" and keep in inbox
+</example_rules>
 
 Focus on creating rules that will help the user organize their inbox more efficiently, save time, and automate responses where appropriate. Consider the following aspects:
 
@@ -56,9 +97,15 @@ Focus on creating rules that will help the user organize their inbox more effici
 4. Forwarding specific types of emails to relevant team members
 5. Prioritizing important or urgent emails
 6. Dealing with newsletters, marketing emails, and potential spam
+${
+  hasSnippets
+    ? "7. Add a rule for each snippet. IMPORTANT: Include the full text of the snippet in your output. The output can be multiple paragraphs long when using snippets."
+    : ""
+}
+
+Your response should only include the list of general rules. Aim for 3-10 broadly applicable rules that would be useful for this user's email management.`;
 
-Your response should only include the list of general rules. Aim for 3-15 broadly applicable rules that would be useful for this user's email management.
-`;
+  logger.trace({ system, prompt });
 
   const aiResponse = await chatCompletionTools({
     userAi: user,
@@ -67,16 +114,28 @@ Your response should only include the list of general rules. Aim for 3-15 broadl
     tools: {
       generate_rules: {
         description: "Generate a list of email management rules",
-        parameters,
+        parameters: hasSnippets ? parametersSnippets : parameters,
       },
     },
-    userEmail: user.email,
+    userEmail: user.email || "",
     label: "Generate rules prompt",
   });
 
-  const parsedRules = aiResponse.toolCalls[0].args as z.infer<
-    typeof parameters
-  >;
+  const args = aiResponse.toolCalls[0].args;
+
+  logger.trace(args);
+
+  return parseRulesResponse(args, hasSnippets);
+}
+
+function parseRulesResponse(args: unknown, hasSnippets: boolean): string[] {
+  if (hasSnippets) {
+    const parsedRules = args as z.infer<typeof parametersSnippets>;
+    return parsedRules.rules.map(({ rule, snippet }) =>
+      snippet ? `${rule}\n<snippet>\n${snippet}\n</snippet>` : rule,
+    );
+  }
 
+  const parsedRules = args as z.infer<typeof parameters>;
   return parsedRules.rules;
 }
diff --git a/apps/web/utils/ai/rule/prompt-to-rules.ts b/apps/web/utils/ai/rule/prompt-to-rules.ts
index f1cd349f31..d1fe865d85 100644
--- a/apps/web/utils/ai/rule/prompt-to-rules.ts
+++ b/apps/web/utils/ai/rule/prompt-to-rules.ts
@@ -2,6 +2,9 @@ import { z } from "zod";
 import { chatCompletionTools } from "@/utils/llms";
 import type { UserAIFields } from "@/utils/llms/types";
 import { createRuleSchema } from "@/utils/ai/rule/create-rule-schema";
+import { createScopedLogger } from "@/utils/logger";
+
+const logger = createScopedLogger("ai-prompt-to-rules");
 
 const updateRuleSchema = createRuleSchema.extend({
   ruleId: z.string().optional(),
@@ -26,7 +29,15 @@ export async function aiPromptToRules({
 
   const system =
     "You are an AI assistant that converts email management rules into a structured format. Parse the given prompt file and conver them into rules.";
-  const prompt = `Convert the following prompt file into rules: ${promptFile}`;
+  const prompt = `Convert the following prompt file into rules:
+  
+<prompt>
+${promptFile}
+</prompt>
+
+IMPORTANT: If a user provides a snippet, use that full snippet in the rule. Don't include placeholders unless it's clear one is needed.`;
+
+  logger.trace({ system, prompt });
 
   const aiResponse = await chatCompletionTools({
     userAi: user,
@@ -46,6 +57,8 @@ export async function aiPromptToRules({
     rules: z.infer<typeof updateRuleSchema>[];
   };
 
+  logger.trace({ parsedRules });
+
   return parsedRules.rules.map((rule) => ({
     ...rule,
     actions: rule.actions.map((action) => ({
diff --git a/apps/web/utils/ai/snippets/find-snippets.ts b/apps/web/utils/ai/snippets/find-snippets.ts
new file mode 100644
index 0000000000..13a62f580f
--- /dev/null
+++ b/apps/web/utils/ai/snippets/find-snippets.ts
@@ -0,0 +1,80 @@
+import { z } from "zod";
+import {
+  type EmailForLLM,
+  stringifyEmail,
+} from "@/utils/ai/choose-rule/stringify-email";
+import { chatCompletionObject } from "@/utils/llms";
+import type { UserAIFields } from "@/utils/llms/types";
+import type { User } from "@prisma/client";
+import { createScopedLogger } from "@/utils/logger";
+
+const logger = createScopedLogger("AI Find Snippets");
+
+const snippetsSchema = z.object({
+  snippets: z.array(
+    z.object({
+      text: z.string(),
+      count: z.number(),
+    }),
+  ),
+});
+
+export type SnippetsResponse = z.infer<typeof snippetsSchema>;
+
+export async function aiFindSnippets({
+  user,
+  sentEmails,
+}: {
+  user: Pick<User, "email" | "about"> & UserAIFields;
+  sentEmails: EmailForLLM[];
+}) {
+  const system = `You are an AI assistant that analyzes email content to find common snippets (canned responses) that the user frequently uses.
+
+<instructions>
+1. Analyze the provided email contents
+2. Identify recurring responses that appear multiple times across different emails
+3. Return only the most meaningful and frequently used snippets
+4. Exclude generic phrases like "Best regards" or "Thanks"
+5. Generate the text for the snippet from the email content and try to keep it as close to possible to the original text.
+6. If no meaningful recurring snippets are found, return an empty array
+</instructions>
+
+Return the snippets in the following JSON format:
+
+<example_response>
+{
+  "snippets": [
+    {
+      "text": "I've reviewed your proposal and I'm interested in learning more. Could we schedule a call next week to discuss the details? I'm generally available between 2-5pm EST.",
+      "count": 8
+    },
+    {
+      "text": "I wanted to follow up on our conversation from last week. Have you had a chance to review the documents I sent over?",
+      "count": 15
+    },
+    {
+      "text": "We're currently in the process of evaluating several vendors. I'll be sure to include your proposal in our review and will get back to you with our decision by the end of next week.",
+      "count": 4
+    }
+  ]
+}
+</example_response>`;
+
+  const prompt = `Here are the emails to analyze:
+${sentEmails
+  .map((email) => `<email>${stringifyEmail(email, 2_000)}</email>`)
+  .join("\n")}`;
+
+  const aiResponse = await chatCompletionObject({
+    userAi: user,
+    prompt,
+    system,
+    schema: snippetsSchema,
+    userEmail: user.email ?? "",
+    usageLabel: "ai-find-snippets",
+  });
+
+  logger.trace({ snippets: aiResponse.object.snippets });
+
+  return aiResponse.object;
+}
diff --git a/apps/web/utils/gmail/label.ts b/apps/web/utils/gmail/label.ts
index fc62b22206..36a65cf164 100644
--- a/apps/web/utils/gmail/label.ts
+++ b/apps/web/utils/gmail/label.ts
@@ -6,8 +6,20 @@ import {
   type InboxZeroLabel,
 } from "@/utils/label";
 
-type MessageVisibility = "show" | "hide";
-type LabelVisibility = "labelShow" | "labelShowIfUnread" | "labelHide";
+export const messageVisibility = {
+  show: "show",
+  hide: "hide",
+} as const;
+export type MessageVisibility =
+  (typeof messageVisibility)[keyof typeof messageVisibility];
+
+export const labelVisibility = {
+  labelShow: "labelShow",
+  labelShowIfUnread: "labelShowIfUnread",
+  labelHide: "labelHide",
+} as const;
+export type LabelVisibility =
+  (typeof labelVisibility)[keyof typeof labelVisibility];
 
 export const INBOX_LABEL_ID = "INBOX";
 export const SENT_LABEL_ID = "SENT";
@@ -178,7 +190,11 @@ async function createLabel({
 }
 
 export async function getLabels(gmail: gmail_v1.Gmail) {
-  return (await gmail.users.labels.list({ userId: "me" })).data.labels;
+  const response = await gmail.users.labels.list({
+    userId: "me",
+    fields: "labels(id,name,messagesTotal,messagesUnread,type,color)",
+  });
+  return response.data.labels;
 }
 
 export async function getLabel(options: {
diff --git a/apps/web/utils/llms/index.ts b/apps/web/utils/llms/index.ts
index c955d792e3..e6ae4dfb05 100644
--- a/apps/web/utils/llms/index.ts
+++ b/apps/web/utils/llms/index.ts
@@ -198,6 +198,52 @@ export async function chatCompletionTools({
   }
 }
 
+// not in use atm
+async function streamCompletionTools({
+  userAi,
+  prompt,
+  system,
+  tools,
+  maxSteps,
+  userEmail,
+  label,
+  onFinish,
+}: {
+  userAi: UserAIFields;
+  prompt: string;
+  system?: string;
+  tools: Record<string, CoreTool>;
+  maxSteps?: number;
+  userEmail: string;
+  label: string;
+  onFinish?: (text: string) => Promise<void>;
+}) {
+  const { provider, model, llmModel } = getModel(userAi);
+
+  const result = await streamText({
+    model: llmModel,
+    tools,
+    toolChoice: "required",
+    prompt,
+    system,
+    maxSteps,
+    experimental_telemetry: { isEnabled: true },
+    onFinish: async ({ usage, text }) => {
+      await saveAiUsage({
+        email: userEmail,
+        provider,
+        model,
+        usage,
+        label,
+      });
+
+      if (onFinish) await onFinish(text);
+    },
+  });
+
+  return result;
+}
+
 export async function withRetry<T>(
   fn: () => Promise<T>,
   {