diff --git a/apps/web/__tests__/ai-prompt-to-rules.test.ts b/apps/web/__tests__/ai-prompt-to-rules.test.ts
index 53f7394044..d16c7569a8 100644
--- a/apps/web/__tests__/ai-prompt-to-rules.test.ts
+++ b/apps/web/__tests__/ai-prompt-to-rules.test.ts
@@ -31,6 +31,7 @@ describe.skipIf(!isAiTest)("aiPromptToRules", () => {
       user,
       promptFile,
       isEditing: false,
+      hasSmartCategories: false,
     });
 
     console.log(JSON.stringify(result, null, 2));
@@ -122,7 +123,12 @@ describe.skipIf(!isAiTest)("aiPromptToRules", () => {
     const promptFile = "Some prompt";
 
     await expect(
-      aiPromptToRules({ user, promptFile, isEditing: false }),
+      aiPromptToRules({
+        user,
+        promptFile,
+        isEditing: false,
+        hasSmartCategories: false,
+      }),
     ).rejects.toThrow();
   });
 });
diff --git a/apps/web/app/(app)/automation/RulesPrompt.tsx b/apps/web/app/(app)/automation/RulesPrompt.tsx
index 4ba3c9cf83..94cb618f74 100644
--- a/apps/web/app/(app)/automation/RulesPrompt.tsx
+++ b/apps/web/app/(app)/automation/RulesPrompt.tsx
@@ -63,8 +63,12 @@ export function RulesPrompt() {
           mutate={mutate}
           onOpenPersonaDialog={onOpenPersonaDialog}
         />
+        <AutomationOnboarding
+          onComplete={() => {
+            if (!data?.rulesPrompt) onOpenPersonaDialog();
+          }}
+        />
       </LoadingContent>
-      <AutomationOnboarding onComplete={onOpenPersonaDialog} />
       <PersonaDialog
         isOpen={isModalOpen}
         setIsOpen={setIsModalOpen}
@@ -220,7 +224,7 @@ Let me know if you're interested!
 </email>`}
                 />
 
-                <div className="flex gap-2">
+                <div className="flex flex-wrap gap-2">
                   <Button
                     type="submit"
                     disabled={isSubmitting || isGenerating}
@@ -286,7 +290,7 @@ Let me know if you're interested!
             </form>
           </CardContent>
         </div>
-        <div className="px-6 pb-4 sm:mt-8 sm:p-0">
+        <div className="px-4 pb-4 sm:mt-8 sm:p-0 sm:px-6">
           <SectionHeader>Examples</SectionHeader>
 
           <ScrollArea className="mt-2 sm:h-[600px] sm:max-h-[600px]">
diff --git a/apps/web/components/NavBottom.tsx b/apps/web/components/NavBottom.tsx
index 63b4ed898e..d777db1a9b 100644
--- a/apps/web/components/NavBottom.tsx
+++ b/apps/web/components/NavBottom.tsx
@@ -26,7 +26,7 @@ function NavBarBottom({
       // safe area for iOS PWA
       style={{ paddingBottom: "env(safe-area-inset-bottom)" }}
     >
-      <nav className="flex h-14 items-center justify-around">
+      <nav className="grid h-14 grid-cols-4">
         {links.map((link) => {
           return (
             <Link
@@ -50,7 +50,7 @@ function NavBarBottom({
 const links = [
   {
     path: "/automation",
-    label: "AI Personal Assistant",
+    label: "Assistant",
     icon: SparklesIcon,
   },
   {
diff --git a/apps/web/utils/actions/ai-rule.ts b/apps/web/utils/actions/ai-rule.ts
index ee75e8c220..e86554fdec 100644
--- a/apps/web/utils/actions/ai-rule.ts
+++ b/apps/web/utils/actions/ai-rule.ts
@@ -543,6 +543,7 @@ export const saveRulesPromptAction = withActionInstrumentation(
         aiModel: true,
         aiApiKey: true,
         email: true,
+        categories: { select: { id: true } },
       },
     });
 
@@ -572,6 +573,8 @@ export const saveRulesPromptAction = withActionInstrumentation(
     let editRulesCount = 0;
     let removeRulesCount = 0;
 
+    const hasSmartCategories = user.categories.length > 0;
+
     // check how the prompts have changed, and make changes to the rules accordingly
     if (oldPromptFile) {
       logger.info("Comparing old and new prompts", {
@@ -609,6 +612,7 @@ export const saveRulesPromptAction = withActionInstrumentation(
           user: { ...user, email: user.email },
           promptFile: diff.addedRules.join("\n\n"),
           isEditing: false,
+          hasSmartCategories,
         });
         logger.info("Added rules", {
           email: user.email,
@@ -691,6 +695,7 @@ export const saveRulesPromptAction = withActionInstrumentation(
             )
             .join("\n\n"),
           isEditing: true,
+          hasSmartCategories,
         });
 
         for (const rule of editedRules) {
@@ -736,6 +741,7 @@ export const saveRulesPromptAction = withActionInstrumentation(
         user: { ...user, email: user.email },
         promptFile: data.rulesPrompt,
         isEditing: false,
+        hasSmartCategories,
       });
       logger.info("Rules to be added", {
         email: user.email,
diff --git a/apps/web/utils/ai/rule/create-rule-schema.ts b/apps/web/utils/ai/rule/create-rule-schema.ts
index 873e85c287..6292511c1e 100644
--- a/apps/web/utils/ai/rule/create-rule-schema.ts
+++ b/apps/web/utils/ai/rule/create-rule-schema.ts
@@ -1,47 +1,52 @@
 import { z } from "zod";
 import { GroupName } from "@/utils/config";
-import { ActionType, RuleType } from "@prisma/client";
+import { ActionType, CategoryFilterType, RuleType } from "@prisma/client";
+
+const typeSchema = z.enum([RuleType.AI, RuleType.STATIC, RuleType.GROUP]);
+const allTypesSchema = z.enum([
+  RuleType.AI,
+  RuleType.STATIC,
+  RuleType.GROUP,
+  RuleType.CATEGORY,
+]);
+
+const conditionSchema = z
+  .object({
+    aiInstructions: z
+      .string()
+      .optional()
+      .describe(
+        "Instructions for the AI to determine when to apply this rule. For example: 'Apply this rule to emails about product updates' or 'Use this rule for messages discussing project deadlines'. Be specific about the email content or characteristics that should trigger this rule. Leave blank if using static conditions or groups.",
+      ),
+    static: z
+      .object({
+        from: z.string().optional().describe("The from email address to match"),
+        to: z.string().optional().describe("The to email address to match"),
+        subject: z
+          .string()
+          .optional()
+          .describe(
+            "The subject to match. Leave blank if AI is required to process the subject line.",
+          ),
+      })
+      .optional()
+      .describe("The static conditions to match"),
+    group: z
+      .enum([GroupName.RECEIPT, GroupName.NEWSLETTER])
+      .optional()
+      .describe(
+        "The group to match. Only 'Receipt' and 'Newsletter' are supported.",
+      ),
+  })
+  .describe("The conditions to match");
 
 export const createRuleSchema = z.object({
   name: z
     .string()
     .describe("The name of the rule. No need to include 'Rule' in the name."),
-  condition: z
-    .object({
-      type: z
-        .enum([RuleType.AI, RuleType.STATIC, RuleType.GROUP])
-        .describe("The type of the condition"),
-
-      aiInstructions: z
-        .string()
-        .optional()
-        .describe(
-          "Instructions for the AI to determine when to apply this rule. For example: 'Apply this rule to emails about product updates' or 'Use this rule for messages discussing project deadlines'. Be specific about the email content or characteristics that should trigger this rule. Leave blank if using static conditions or groups.",
-        ),
-      static: z
-        .object({
-          from: z
-            .string()
-            .optional()
-            .describe("The from email address to match"),
-          to: z.string().optional().describe("The to email address to match"),
-          subject: z
-            .string()
-            .optional()
-            .describe(
-              "The subject to match. Leave blank if AI is required to process the subject line.",
-            ),
-        })
-        .optional()
-        .describe("The static conditions to match"),
-      group: z
-        .enum([GroupName.RECEIPT, GroupName.NEWSLETTER])
-        .optional()
-        .describe(
-          "The group to match. Only 'Receipt' and 'Newsletter' are supported.",
-        ),
-    })
-    .describe("The conditions to match"),
+  condition: conditionSchema.extend({
+    type: typeSchema.describe("The type of the condition"),
+  }),
   actions: z
     .array(
       z.object({
@@ -78,6 +83,11 @@ export const createRuleSchema = z.object({
               .nullish()
               .transform((v) => v ?? null)
               .describe("The content of the email"),
+            webhookUrl: z
+              .string()
+              .nullish()
+              .transform((v) => v ?? null)
+              .describe("The webhook URL to call"),
           })
           .optional()
           .describe(
@@ -87,3 +97,19 @@ export const createRuleSchema = z.object({
     )
     .describe("The actions to take"),
 });
+
+export const createRuleSchemaWithCategories = createRuleSchema.extend({
+  condition: conditionSchema.extend({
+    type: allTypesSchema.describe("The type of the condition"),
+    categoryFilterType: z
+      .enum([CategoryFilterType.INCLUDE, CategoryFilterType.EXCLUDE])
+      .optional()
+      .describe(
+        "Whether senders in this categoryFilters should be included or excluded",
+      ),
+    categoryFilters: z
+      .array(z.string())
+      .optional()
+      .describe("The categories to match"),
+  }),
+});
diff --git a/apps/web/utils/ai/rule/create-rule.ts b/apps/web/utils/ai/rule/create-rule.ts
index acc78355ff..8e4b240792 100644
--- a/apps/web/utils/ai/rule/create-rule.ts
+++ b/apps/web/utils/ai/rule/create-rule.ts
@@ -40,6 +40,7 @@ export async function aiCreateRule(
       bcc: action.fields?.bcc ?? undefined,
       subject: action.fields?.subject ?? undefined,
       content: action.fields?.content ?? undefined,
+      webhookUrl: action.fields?.webhookUrl ?? undefined,
     })),
   };
 }
diff --git a/apps/web/utils/ai/rule/prompt-to-rules.ts b/apps/web/utils/ai/rule/prompt-to-rules.ts
index a53e1667eb..db9b755aea 100644
--- a/apps/web/utils/ai/rule/prompt-to-rules.ts
+++ b/apps/web/utils/ai/rule/prompt-to-rules.ts
@@ -1,7 +1,10 @@
 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 {
+  createRuleSchema,
+  createRuleSchemaWithCategories,
+} from "@/utils/ai/rule/create-rule-schema";
 import { createScopedLogger } from "@/utils/logger";
 
 const logger = createScopedLogger("ai-prompt-to-rules");
@@ -9,17 +12,30 @@ const logger = createScopedLogger("ai-prompt-to-rules");
 const updateRuleSchema = createRuleSchema.extend({
   ruleId: z.string().optional(),
 });
+const updateRuleSchemaWithCategories = createRuleSchemaWithCategories.extend({
+  ruleId: z.string().optional(),
+});
 
 export async function aiPromptToRules({
   user,
   promptFile,
   isEditing,
+  hasSmartCategories,
 }: {
   user: UserAIFields & { email: string };
   promptFile: string;
   isEditing: boolean;
+  hasSmartCategories: boolean;
 }) {
-  const schema = isEditing ? updateRuleSchema : createRuleSchema;
+  function getSchema() {
+    if (hasSmartCategories)
+      return isEditing
+        ? updateRuleSchemaWithCategories
+        : createRuleSchemaWithCategories;
+    return isEditing ? updateRuleSchema : createRuleSchema;
+  }
+
+  const schema = getSchema();
 
   const parameters = z.object({
     rules: z
@@ -69,6 +85,7 @@ IMPORTANT: If a user provides a snippet, use that full snippet in the rule. Don'
       bcc: action.fields?.bcc ?? undefined,
       subject: action.fields?.subject ?? undefined,
       content: action.fields?.content ?? undefined,
+      webhookUrl: action.fields?.webhookUrl ?? undefined,
     })),
   }));
 }