diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5394d6ec..7c847f1e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,7 @@ and this project adheres to [Semantic Versioning](http://semver.org/).
 ## Added
 
 - Added foundation for upcoming authentication from iOS app.
+- [Dawarich Cloud] Trial users can now create up to 5 imports. After that, they will be prompted to subscribe to a paid plan.
 
 
 # [0.32.0] - 2025-09-13
diff --git a/app/javascript/controllers/direct_upload_controller.js b/app/javascript/controllers/direct_upload_controller.js
index cc58436e..269595b4 100644
--- a/app/javascript/controllers/direct_upload_controller.js
+++ b/app/javascript/controllers/direct_upload_controller.js
@@ -6,7 +6,8 @@ export default class extends Controller {
   static targets = ["input", "progress", "progressBar", "submit", "form"]
   static values = {
     url: String,
-    userTrial: Boolean
+    userTrial: Boolean,
+    currentImportsCount: Number
   }
 
   connect() {
@@ -51,6 +52,16 @@ export default class extends Controller {
     const files = this.inputTarget.files
     if (files.length === 0) return
 
+    // Check import count limits for trial users
+    if (this.userTrialValue && this.currentImportsCountValue >= 5) {
+      const message = 'Import limit reached. Trial users can only create up to 5 imports. Please subscribe to import more files.'
+      showFlashMessage('error', message)
+
+      // Clear the file input
+      this.inputTarget.value = ''
+      return
+    }
+
     // Check file size limits for trial users
     if (this.userTrialValue) {
       const MAX_FILE_SIZE = 11 * 1024 * 1024 // 11MB in bytes
diff --git a/app/models/import.rb b/app/models/import.rb
index b1abde92..4544819e 100644
--- a/app/models/import.rb
+++ b/app/models/import.rb
@@ -15,6 +15,7 @@ class Import < ApplicationRecord
 
   validates :name, presence: true, uniqueness: { scope: :user_id }
   validate :file_size_within_limit, if: -> { user.trial? }
+  validate :import_count_within_limit, if: -> { user.trial? }
 
   enum :status, { created: 0, processing: 1, completed: 2, failed: 3 }
 
@@ -69,6 +70,15 @@ class Import < ApplicationRecord
     errors.add(:file, 'is too large. Trial users can only upload files up to 10MB.')
   end
 
+  def import_count_within_limit
+    return unless new_record?
+
+    existing_imports_count = user.imports.count
+    return unless existing_imports_count >= 5
+
+    errors.add(:base, 'Trial users can only create up to 5 imports. Please subscribe to import more files.')
+  end
+
   def recalculate_stats
     years_and_months_tracked.each do |year, month|
       Stats::CalculatingJob.perform_later(user.id, year, month)
diff --git a/app/views/imports/_form.html.erb b/app/views/imports/_form.html.erb
index 95d16411..16fd3cd5 100644
--- a/app/views/imports/_form.html.erb
+++ b/app/views/imports/_form.html.erb
@@ -11,6 +11,13 @@
     <div class="text-xs text-gray-500 mt-2">
       File format is automatically detected during upload.
     </div>
+    <% if current_user.trial? %>
+      <div class="text-xs text-orange-600 mt-2 font-medium">
+        Trial limitations: Max 5 imports, 10MB per file.
+        <br>
+        Current imports: <%= current_user.imports.count %>/5
+      </div>
+    <% end %>
   </div>
 </div>
 
@@ -18,6 +25,7 @@
   controller: "direct-upload",
   direct_upload_url_value: rails_direct_uploads_url,
   direct_upload_user_trial_value: current_user.trial?,
+  direct_upload_current_imports_count_value: current_user.imports.count,
   direct_upload_target: "form"
 } do |form| %>
   <label class="form-control w-full max-w-xs my-5">
diff --git a/spec/models/import_spec.rb b/spec/models/import_spec.rb
index fec9ad1f..2a90c2aa 100644
--- a/spec/models/import_spec.rb
+++ b/spec/models/import_spec.rb
@@ -66,6 +66,42 @@ RSpec.describe Import, type: :model do
         end
       end
     end
+
+    describe 'import count validation' do
+      context 'when user is a trial user' do
+        let(:user) do
+          user = create(:user)
+          user.update!(status: :trial)
+          user
+        end
+
+        it 'allows imports when under the limit' do
+          3.times { |i| create(:import, user: user, name: "import_#{i}") }
+          new_import = build(:import, user: user, name: 'new_import')
+
+          expect(new_import).to be_valid
+        end
+
+        it 'prevents creating more than 5 imports' do
+          5.times { |i| create(:import, user: user, name: "import_#{i}") }
+          new_import = build(:import, user: user, name: 'import_6')
+
+          expect(new_import).not_to be_valid
+          expect(new_import.errors[:base]).to include('Trial users can only create up to 5 imports. Please subscribe to import more files.')
+        end
+      end
+
+      context 'when user is an active user' do
+        let(:user) { create(:user, status: :active) }
+
+        it 'does not validate import count limit' do
+          7.times { |i| create(:import, user: user, name: "import_#{i}") }
+          new_import = build(:import, user: user, name: 'import_8')
+
+          expect(new_import).to be_valid
+        end
+      end
+    end
   end
 
   describe 'enums' do