diff --git a/app/Http/Requests/BankTransaction/MatchBankTransactionRequest.php b/app/Http/Requests/BankTransaction/MatchBankTransactionRequest.php
index 34c328028533..585a7c967399 100644
--- a/app/Http/Requests/BankTransaction/MatchBankTransactionRequest.php
+++ b/app/Http/Requests/BankTransaction/MatchBankTransactionRequest.php
@@ -47,7 +47,7 @@ class MatchBankTransactionRequest extends Request
     public function prepareForValidation()
     {
         $inputs = $this->all();
-        
+        nlog($inputs);
         foreach ($inputs['transactions'] as $key => $input) {
             if (array_key_exists('id', $inputs['transactions'][$key])) {
                 $inputs['transactions'][$key]['id'] = $this->decodePrimaryKey($input['id']);
@@ -73,6 +73,7 @@ class MatchBankTransactionRequest extends Request
 
             if (array_key_exists('expense_id', $inputs['transactions'][$key]) && strlen($inputs['transactions'][$key]['expense_id']) >= 1) {
                 $inputs['transactions'][$key]['expense_id'] = $this->decodePrimaryKey($inputs['transactions'][$key]['expense_id']);
+
                 $e = Expense::withTrashed()->where('company_id', auth()->user()->company()->id)->where('id', $inputs['transactions'][$key]['expense_id'])->first();
 
                 /*Ensure we don't relink an existing expense*/
@@ -82,6 +83,8 @@ class MatchBankTransactionRequest extends Request
             }
         }
 
+        nlog($inputs);
+
         $this->replace($inputs);
     }
 }
diff --git a/app/Jobs/Bank/MatchBankTransactions.php b/app/Jobs/Bank/MatchBankTransactions.php
index 1a18fc72db18..34fd6db48b99 100644
--- a/app/Jobs/Bank/MatchBankTransactions.php
+++ b/app/Jobs/Bank/MatchBankTransactions.php
@@ -152,7 +152,7 @@ class MatchBankTransactions implements ShouldQueue
     {
         $this->bt = BankTransaction::find($input['id']);
 
-        if (!$this->bt || $this->bt->status_id == BankTransaction::STATUS_CONVERTED) {
+        if (!$this->bt) {
             return $this;
         }
 
@@ -176,9 +176,13 @@ class MatchBankTransactions implements ShouldQueue
 
     private function coalesceExpenses($expense): string 
     {
+nlog("BTExpense: " . $this->bt->expense_id);
 
-        if(!$this->bt->expense_id || strlen($this->bt->expense_id) < 1)
-            return $expense;
+    if (!$this->bt->expense_id || strlen($this->bt->expense_id) < 1) {
+        nlog("coalesceExpense: " . $expense);
+        return $expense;
+    }
+        nlog("coalesceExpenses: " . $this->bt->expense_id . "," . $expense);
 
         return collect(explode(",", $this->bt->expense_id))->push($expense)->implode(",");
     }
@@ -259,7 +263,7 @@ class MatchBankTransactions implements ShouldQueue
         $expense->should_be_invoiced = $this->company->mark_expenses_invoiceable;
         $expense->save();
 
-        $this->bt->expense_id = $expense->hashed_id;
+        $this->bt->expense_id = $this->coalesceExpenses($expense->hashed_id);
 
         if (array_key_exists('vendor_id', $input)) {
             $this->bt->vendor_id = $input['vendor_id'];
diff --git a/app/Models/Expense.php b/app/Models/Expense.php
index f4a48d1cf35a..6c8718ba7276 100644
--- a/app/Models/Expense.php
+++ b/app/Models/Expense.php
@@ -259,4 +259,10 @@ class Expense extends BaseModel
     {
         return $this->belongsTo(Project::class);
     }
+
+    public function transaction()
+    {
+        return $this->belongsTo(BankTransaction::class);
+    }
+
 }
diff --git a/app/Repositories/ExpenseRepository.php b/app/Repositories/ExpenseRepository.php
index b1eb36d05a5b..6b2770590b85 100644
--- a/app/Repositories/ExpenseRepository.php
+++ b/app/Repositories/ExpenseRepository.php
@@ -102,9 +102,19 @@ class ExpenseRepository extends BaseRepository
 
     public function delete($expense) :Expense
     {
+        
         if ($expense->transaction_id) {
+            
+            $exp_ids = collect(explode(',', $expense->transaction->expense_id))->filter(function ($id) use ($expense) {
+                return $id != $expense->hashed_id;
+            })->implode(',');
+                    
             $expense->transaction_id = null;
             $expense->saveQuietly();
+
+            $expense->transaction->expense_id = $exp_ids;
+            $expense->transaction->saveQuietly();
+
         }
 
         parent::delete($expense);
diff --git a/tests/Feature/Bank/BankTransactionTest.php b/tests/Feature/Bank/BankTransactionTest.php
index 96cce05ae155..9a58c2b631e3 100644
--- a/tests/Feature/Bank/BankTransactionTest.php
+++ b/tests/Feature/Bank/BankTransactionTest.php
@@ -12,15 +12,16 @@
 
 namespace Tests\Feature\Bank;
 
+use Tests\TestCase;
+use App\Models\Expense;
+use App\Models\Invoice;
+use Tests\MockAccountData;
+use App\Factory\InvoiceFactory;
+use App\Models\BankTransaction;
+use App\Factory\InvoiceItemFactory;
 use App\Factory\BankIntegrationFactory;
 use App\Factory\BankTransactionFactory;
-use App\Factory\InvoiceFactory;
-use App\Factory\InvoiceItemFactory;
-use App\Models\BankTransaction;
-use App\Models\Invoice;
 use Illuminate\Foundation\Testing\DatabaseTransactions;
-use Tests\MockAccountData;
-use Tests\TestCase;
 
 class BankTransactionTest extends TestCase
 {
@@ -38,6 +39,167 @@ class BankTransactionTest extends TestCase
         );
     }
 
+    public function testLinkMultipleExpensesWithDeleteToTransaction()
+    {
+        $data = [];
+
+        $bi = BankIntegrationFactory::create($this->company->id, $this->user->id, $this->account->id);
+        $bi->save();
+
+        $bt = BankTransactionFactory::create($this->company->id, $this->user->id);
+        $bt->bank_integration_id = $bi->id;
+        $bt->status_id = BankTransaction::STATUS_UNMATCHED;
+        $bt->description = 'Fuel';
+        $bt->amount = 10;
+        $bt->currency_code = $this->client->currency()->code;
+        $bt->date = now()->format('Y-m-d');
+        $bt->transaction_id = 1234567890;
+        $bt->category_id = 10000003;
+        $bt->base_type = 'DEBIT';
+        $bt->save();
+
+        $this->expense->vendor_id = $this->vendor->id;
+        $this->expense->save();
+
+        $data = [];
+
+        $data['transactions'][] = [
+            'id' => $bt->hashed_id,
+            'expense_id' => $this->expense->hashed_id
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson('/api/v1/bank_transactions/match', $data);
+
+        $response->assertStatus(200);
+
+        $this->assertEquals($this->expense->refresh()->transaction_id, $bt->id);
+        $this->assertEquals($this->expense->hashed_id, $bt->refresh()->expense_id);
+        $this->assertEquals($this->vendor->id, $bt->vendor_id);
+        $this->assertEquals(BankTransaction::STATUS_CONVERTED, $bt->status_id);
+
+
+        $e = Expense::factory()->create([
+            'company_id' => $this->company->id,
+            'user_id' => $this->user->id,
+        ]);
+
+        $data = [];
+
+        $data['transactions'][] = [
+            'id' => $bt->hashed_id,
+            'expense_id' => $e->hashed_id
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson('/api/v1/bank_transactions/match', $data);
+
+        $response->assertStatus(200);
+
+        $this->assertEquals("{$this->expense->hashed_id},{$e->hashed_id}", $bt->fresh()->expense_id);
+
+        $e2 = Expense::factory()->create([
+            'company_id' => $this->company->id,
+            'user_id' => $this->user->id,
+        ]);
+
+        $data = [];
+
+        $data['transactions'][] = [
+            'id' => $bt->hashed_id,
+            'expense_id' => $e2->hashed_id
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson('/api/v1/bank_transactions/match', $data);
+
+        $response->assertStatus(200);
+
+        $this->assertNotNull($e2->refresh()->transaction_id);
+        
+        $this->assertEquals("{$this->expense->hashed_id},{$e->hashed_id},{$e2->hashed_id}", $bt->fresh()->expense_id);
+
+        $expense_repo = app('App\Repositories\ExpenseRepository');
+
+        $expense_repo->delete($e2);
+
+        $this->assertEquals("{$this->expense->hashed_id},{$e->hashed_id}", $bt->fresh()->expense_id);
+
+    }
+
+
+
+    public function testLinkMultipleExpensesToTransaction()
+    {
+        $data = [];
+
+        $bi = BankIntegrationFactory::create($this->company->id, $this->user->id, $this->account->id);
+        $bi->save();
+
+        $bt = BankTransactionFactory::create($this->company->id, $this->user->id);
+        $bt->bank_integration_id = $bi->id;
+        $bt->status_id = BankTransaction::STATUS_UNMATCHED;
+        $bt->description = 'Fuel';
+        $bt->amount = 10;
+        $bt->currency_code = $this->client->currency()->code;
+        $bt->date = now()->format('Y-m-d');
+        $bt->transaction_id = 1234567890;
+        $bt->category_id = 10000003;
+        $bt->base_type = 'DEBIT';
+        $bt->save();
+
+        $this->expense->vendor_id = $this->vendor->id;
+        $this->expense->save();
+
+        $data = [];
+
+        $data['transactions'][] = [
+            'id' => $bt->hashed_id,
+            'expense_id' => $this->expense->hashed_id
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson('/api/v1/bank_transactions/match', $data);
+
+        $response->assertStatus(200);
+
+        $this->assertEquals($this->expense->refresh()->transaction_id, $bt->id);
+        $this->assertEquals($this->expense->hashed_id, $bt->refresh()->expense_id);
+        $this->assertEquals($this->vendor->id, $bt->vendor_id);
+        $this->assertEquals(BankTransaction::STATUS_CONVERTED, $bt->status_id);
+
+
+        $e = Expense::factory()->create([
+            'company_id' => $this->company->id,
+            'user_id' => $this->user->id,
+        ]);
+
+        $data = [];
+
+        $data['transactions'][] = [
+            'id' => $bt->hashed_id,
+            'expense_id' => $e->hashed_id
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson('/api/v1/bank_transactions/match', $data);
+
+        $response->assertStatus(200);
+
+        $this->assertEquals("{$this->expense->hashed_id},{$e->hashed_id}", $bt->fresh()->expense_id);
+
+    }
+
 
     public function testBankTransactionBulkActions()
     {