diff --git a/app/Http/Controllers/Api/ImportDataController.php b/app/Http/Controllers/Api/ImportDataController.php
index a519da52..c0ed71fa 100644
--- a/app/Http/Controllers/Api/ImportDataController.php
+++ b/app/Http/Controllers/Api/ImportDataController.php
@@ -26,7 +26,7 @@ class ImportDataController extends Controller
                 ->orderBy('name')
                 ->get(['id', 'name', 'logo']),
             'automationRules' => $user->automationRules()
-                ->with('category:id,name,icon,color')
+                ->with(['category:id,name,icon,color', 'labels:id,name,color'])
                 ->orderBy('priority')
                 ->get(),
         ]);
diff --git a/app/Http/Controllers/TransactionController.php b/app/Http/Controllers/TransactionController.php
index 7f313a26..44599670 100644
--- a/app/Http/Controllers/TransactionController.php
+++ b/app/Http/Controllers/TransactionController.php
@@ -51,6 +51,7 @@ class TransactionController extends Controller
 
         $automationRules = AutomationRule::query()
             ->where('user_id', $user->id)
+            ->with(['category:id,name,icon,color', 'labels:id,name,color'])
             ->orderBy('priority')
             ->get();
 
@@ -102,6 +103,8 @@ class TransactionController extends Controller
     public function store(StoreTransactionRequest $request): JsonResponse
     {
         $data = $request->validated();
+        $labelIds = $data['label_ids'] ?? null;
+        unset($data['label_ids']);
 
         $transaction = new Transaction([
             ...$data,
@@ -115,6 +118,10 @@ class TransactionController extends Controller
 
         $transaction->save();
 
+        if ($labelIds !== null) {
+            $transaction->labels()->sync($labelIds);
+        }
+
         return response()->json([
             'data' => $transaction->load('labels:id,name,color'),
         ], 201);
diff --git a/app/Http/Middleware/HandleInertiaRequests.php b/app/Http/Middleware/HandleInertiaRequests.php
index 1b2a85c8..c6ac1b6b 100644
--- a/app/Http/Middleware/HandleInertiaRequests.php
+++ b/app/Http/Middleware/HandleInertiaRequests.php
@@ -81,10 +81,16 @@ class HandleInertiaRequests extends Middleware
             'banks' => fn () => $user ? $user->banks()
                 ->orderBy('name')
                 ->get(['id', 'name', 'logo']) : [],
-            'automationRules' => fn () => $user ? $user->automationRules()
-                ->with('category:id,name,icon,color')
-                ->orderBy('priority')
-                ->get() : [],
+            'automationRules' => function () use ($user) {
+                if (! $user) {
+                    return [];
+                }
+
+                return $user->automationRules()
+                    ->with(['category:id,name,icon,color', 'labels:id,name,color'])
+                    ->orderBy('priority')
+                    ->get();
+            },
             'labels' => fn () => $user ? $user->labels()
                 ->orderBy('name')
                 ->get(['id', 'name', 'color']) : [],
diff --git a/app/Http/Requests/Settings/StoreAutomationRuleRequest.php b/app/Http/Requests/Settings/StoreAutomationRuleRequest.php
index 22127d22..c849df87 100644
--- a/app/Http/Requests/Settings/StoreAutomationRuleRequest.php
+++ b/app/Http/Requests/Settings/StoreAutomationRuleRequest.php
@@ -53,6 +53,16 @@ class StoreAutomationRuleRequest extends FormRequest
         ];
     }
 
+    /**
+     * Decode the rules_json string into an array so the model's array cast doesn't double-encode it.
+     */
+    protected function passedValidation(): void
+    {
+        $this->merge([
+            'rules_json' => json_decode($this->rules_json, true),
+        ]);
+    }
+
     /**
      * Configure the validator instance.
      */
diff --git a/app/Http/Requests/Settings/UpdateAutomationRuleRequest.php b/app/Http/Requests/Settings/UpdateAutomationRuleRequest.php
index 982406b7..747a4c08 100644
--- a/app/Http/Requests/Settings/UpdateAutomationRuleRequest.php
+++ b/app/Http/Requests/Settings/UpdateAutomationRuleRequest.php
@@ -53,6 +53,16 @@ class UpdateAutomationRuleRequest extends FormRequest
         ];
     }
 
+    /**
+     * Decode the rules_json string into an array so the model's array cast doesn't double-encode it.
+     */
+    protected function passedValidation(): void
+    {
+        $this->merge([
+            'rules_json' => json_decode($this->rules_json, true),
+        ]);
+    }
+
     /**
      * Configure the validator instance.
      */
diff --git a/resources/js/components/transactions/edit-transaction-dialog.tsx b/resources/js/components/transactions/edit-transaction-dialog.tsx
index 0e6b94b5..46cf48db 100644
--- a/resources/js/components/transactions/edit-transaction-dialog.tsx
+++ b/resources/js/components/transactions/edit-transaction-dialog.tsx
@@ -168,6 +168,8 @@ export function EditTransactionDialog({
         if (mode !== 'create' || automationRules.length === 0) {
             return {
                 categoryId: null,
+                labelIds: [] as string[],
+                matchedLabels: [] as Label[],
                 notes: null,
                 notesIv: null,
                 ruleName: null,
@@ -178,6 +180,8 @@ export function EditTransactionDialog({
         if (!keyString) {
             return {
                 categoryId: null,
+                labelIds: [] as string[],
+                matchedLabels: [] as Label[],
                 notes: null,
                 notesIv: null,
                 ruleName: null,
@@ -204,6 +208,8 @@ export function EditTransactionDialog({
         if (!result) {
             return {
                 categoryId: null,
+                labelIds: [] as string[],
+                matchedLabels: [] as Label[],
                 notes: null,
                 notesIv: null,
                 ruleName: null,
@@ -228,6 +234,8 @@ export function EditTransactionDialog({
 
         return {
             categoryId: result.categoryId,
+            labelIds: result.labelIds || [],
+            matchedLabels: result.labels || [],
             notes: finalNotes || null,
             notesIv: finalNotesIv,
             ruleName: result.rule.title,
@@ -355,13 +363,20 @@ export function EditTransactionDialog({
 
                 let finalCategoryId = categoryId === 'null' ? null : categoryId;
                 let finalNotes = notes.trim();
+                let finalLabelIds = [...selectedLabelIds];
 
-                if (ruleResult.categoryId) {
+                if (ruleResult.categoryId && !finalCategoryId) {
                     finalCategoryId = ruleResult.categoryId;
                 }
                 if (ruleResult.notes) {
                     finalNotes = ruleResult.notes;
                 }
+                if (
+                    ruleResult.labelIds.length > 0 &&
+                    finalLabelIds.length === 0
+                ) {
+                    finalLabelIds = [...ruleResult.labelIds];
+                }
 
                 let encryptedNotes: string | null = null;
                 let notesIv: string | null = null;
@@ -396,6 +411,8 @@ export function EditTransactionDialog({
                     notes: encryptedNotes,
                     notes_iv: notesIv,
                     source: 'manually_created' as const,
+                    label_ids:
+                        finalLabelIds.length > 0 ? finalLabelIds : undefined,
                 });
 
                 const updatedCategory = finalCategoryId
@@ -404,6 +421,10 @@ export function EditTransactionDialog({
                       ) || null
                     : null;
 
+                const transactionLabels = labels.filter((l) =>
+                    finalLabelIds.includes(l.id),
+                );
+
                 const newTransaction: DecryptedTransaction = {
                     ...createdTransaction,
                     decryptedDescription: trimmedDescription,
@@ -413,6 +434,8 @@ export function EditTransactionDialog({
                     bank: selectedAccount.bank?.id
                         ? banks.find((b) => b.id === selectedAccount.bank?.id)
                         : undefined,
+                    labels: transactionLabels,
+                    label_ids: finalLabelIds,
                 };
 
                 if (updateAccountBalance) {
diff --git a/resources/js/components/transactions/import-transactions-drawer.tsx b/resources/js/components/transactions/import-transactions-drawer.tsx
index 719139d2..a690d5d5 100644
--- a/resources/js/components/transactions/import-transactions-drawer.tsx
+++ b/resources/js/components/transactions/import-transactions-drawer.tsx
@@ -378,6 +378,7 @@ export function ImportTransactionsDrawer({
                     let categoryId: string | null = null;
                     let notes: string | null = null;
                     let notesIv: string | null = null;
+                    let labelIds: string[] = [];
 
                     if (key && rules.length > 0) {
                         const ruleMatch = await evaluateRulesForNewTransaction(
@@ -402,6 +403,12 @@ export function ImportTransactionsDrawer({
                                 notes = ruleMatch.note;
                                 notesIv = ruleMatch.noteIv;
                             }
+                            if (
+                                ruleMatch.labelIds &&
+                                ruleMatch.labelIds.length > 0
+                            ) {
+                                labelIds = ruleMatch.labelIds;
+                            }
                         }
                     }
 
@@ -419,6 +426,7 @@ export function ImportTransactionsDrawer({
                         notes: notes,
                         notes_iv: notesIv,
                         source: 'imported' as const,
+                        label_ids: labelIds.length > 0 ? labelIds : undefined,
                     };
 
                     const createdTransaction =
diff --git a/resources/js/components/transactions/transaction-actions-menu.tsx b/resources/js/components/transactions/transaction-actions-menu.tsx
index 436d4bd8..57133d26 100644
--- a/resources/js/components/transactions/transaction-actions-menu.tsx
+++ b/resources/js/components/transactions/transaction-actions-menu.tsx
@@ -16,6 +16,7 @@ import {
 import { useEncryptionKey } from '@/contexts/encryption-key-context';
 import { useReEvaluateAllTransactions } from '@/hooks/use-re-evaluate-all-transactions';
 import { type Account, type Bank } from '@/types/account';
+import { type AutomationRule } from '@/types/automation-rule';
 import { type Category } from '@/types/category';
 import { type DecryptedTransaction } from '@/types/transaction';
 import { Link } from '@inertiajs/react';
@@ -28,6 +29,7 @@ interface TransactionActionsMenuProps {
     categories: Category[];
     accounts: Account[];
     banks: Bank[];
+    automationRules?: AutomationRule[];
     onAddTransaction: () => void;
     transactions: DecryptedTransaction[];
     onReEvaluateComplete?: () => void;
@@ -37,6 +39,7 @@ export function TransactionActionsMenu({
     categories,
     accounts,
     banks,
+    automationRules = [],
     onAddTransaction,
     transactions,
     onReEvaluateComplete,
@@ -81,7 +84,13 @@ export function TransactionActionsMenu({
 
         setIsReEvaluating(true);
         try {
-            await reEvaluateAll(transactions, categories, accounts, banks);
+            await reEvaluateAll(
+                transactions,
+                categories,
+                accounts,
+                banks,
+                automationRules,
+            );
             onReEvaluateComplete?.();
         } finally {
             setIsReEvaluating(false);
@@ -203,6 +212,7 @@ export function TransactionActionsMenu({
                 categories={categories}
                 accounts={accounts}
                 banks={banks}
+                automationRules={automationRules}
             />
         </>
     );
diff --git a/resources/js/lib/rule-engine.ts b/resources/js/lib/rule-engine.ts
index 13037701..048a7e46 100644
--- a/resources/js/lib/rule-engine.ts
+++ b/resources/js/lib/rule-engine.ts
@@ -29,6 +29,14 @@ export interface TransactionData {
 
 function normalizeRuleJson(rulesJson: unknown): unknown {
     if (typeof rulesJson === 'string') {
+        try {
+            const parsed = JSON.parse(rulesJson);
+            if (typeof parsed === 'object' && parsed !== null) {
+                return normalizeRuleJson(parsed);
+            }
+        } catch {
+            // Not JSON, treat as a plain string value
+        }
         return rulesJson.toLowerCase();
     }
 
diff --git a/resources/js/pages/transactions/index.tsx b/resources/js/pages/transactions/index.tsx
index 1edcf4fe..bbc52b48 100644
--- a/resources/js/pages/transactions/index.tsx
+++ b/resources/js/pages/transactions/index.tsx
@@ -1607,6 +1607,7 @@ export default function Transactions({
                                     categories={categories}
                                     accounts={accounts}
                                     banks={banks}
+                                    automationRules={automationRules}
                                     onAddTransaction={() =>
                                         setCreateDialogOpen(true)
                                     }
@@ -1717,6 +1718,7 @@ export default function Transactions({
                 accounts={accounts}
                 banks={banks}
                 labels={labels}
+                automationRules={automationRules}
                 open={createDialogOpen}
                 onOpenChange={setCreateDialogOpen}
                 onSuccess={(transaction) => {
diff --git a/tests/Feature/ImportDataTest.php b/tests/Feature/ImportDataTest.php
new file mode 100644
index 00000000..89ad6523
--- /dev/null
+++ b/tests/Feature/ImportDataTest.php
@@ -0,0 +1,27 @@
+<?php
+
+use App\Models\AutomationRule;
+use App\Models\Category;
+use App\Models\Label;
+use App\Models\User;
+
+use function Pest\Laravel\actingAs;
+
+test('import data endpoint includes automation rules with labels', function () {
+    $user = User::factory()->onboarded()->create();
+    $category = Category::factory()->create(['user_id' => $user->id]);
+    $label = Label::factory()->create(['user_id' => $user->id]);
+
+    $rule = AutomationRule::factory()->create([
+        'user_id' => $user->id,
+        'action_category_id' => $category->id,
+    ]);
+    $rule->labels()->attach($label->id);
+
+    $response = actingAs($user)->getJson('/api/import/data');
+
+    $response->assertSuccessful();
+    $response->assertJsonPath('automationRules.0.category.id', $category->id);
+    $response->assertJsonPath('automationRules.0.labels.0.id', $label->id);
+    $response->assertJsonPath('automationRules.0.labels.0.name', $label->name);
+});
diff --git a/tests/Feature/TransactionTest.php b/tests/Feature/TransactionTest.php
index 1201e0c3..9715b00a 100644
--- a/tests/Feature/TransactionTest.php
+++ b/tests/Feature/TransactionTest.php
@@ -1,6 +1,7 @@
 <?php
 
 use App\Models\Account;
+use App\Models\AutomationRule;
 use App\Models\Budget;
 use App\Models\BudgetPeriod;
 use App\Models\Category;
@@ -31,6 +32,30 @@ test('authenticated users can access transactions page', function () {
     );
 });
 
+test('transactions page includes automation rules with labels', function () {
+    $user = User::factory()->onboarded()->create();
+    $category = Category::factory()->create(['user_id' => $user->id]);
+    $label = Label::factory()->create(['user_id' => $user->id]);
+
+    $rule = AutomationRule::factory()->create([
+        'user_id' => $user->id,
+        'action_category_id' => $category->id,
+    ]);
+    $rule->labels()->attach($label->id);
+
+    $response = actingAs($user)->get(route('transactions.index'));
+
+    $response->assertSuccessful();
+    $response->assertInertia(fn ($page) => $page
+        ->component('transactions/index')
+        ->has('automationRules', 1)
+        ->has('automationRules.0.labels', 1)
+        ->where('automationRules.0.labels.0.id', $label->id)
+        ->where('automationRules.0.labels.0.name', $label->name)
+        ->where('automationRules.0.category.id', $category->id)
+    );
+});
+
 test('authenticated users can access categorize transactions page', function () {
     $user = User::factory()->onboarded()->create();
 
@@ -431,6 +456,34 @@ test('currency_code is required when creating transaction', function () {
     $response->assertJsonValidationErrors(['currency_code']);
 });
 
+test('users can create a transaction with labels', function () {
+    $user = User::factory()->onboarded()->create();
+    $account = Account::factory()->create(['user_id' => $user->id]);
+    $label1 = Label::factory()->create(['user_id' => $user->id]);
+    $label2 = Label::factory()->create(['user_id' => $user->id]);
+
+    $transactionData = [
+        'account_id' => $account->id,
+        'description' => 'encrypted_description',
+        'description_iv' => str_repeat('d', 16),
+        'transaction_date' => '2025-11-11',
+        'amount' => 5000,
+        'currency_code' => 'USD',
+        'source' => 'imported',
+        'label_ids' => [$label1->id, $label2->id],
+    ];
+
+    $response = actingAs($user)->postJson(route('transactions.store'), $transactionData);
+
+    $response->assertCreated();
+
+    $transaction = Transaction::latest()->first();
+    expect($transaction->labels)->toHaveCount(2);
+    expect($transaction->labels->pluck('id')->toArray())->toContain($label1->id, $label2->id);
+
+    $response->assertJsonCount(2, 'data.labels');
+});
+
 test('users can add labels to a transaction', function () {
     $user = User::factory()->onboarded()->create();
     $account = Account::factory()->create(['user_id' => $user->id]);