diff --git a/app/assets/javascripts/discourse/components/composer-editor.js.es6 b/app/assets/javascripts/discourse/components/composer-editor.js.es6
index 9a92e7e14f1..e32c2f5ce6a 100644
--- a/app/assets/javascripts/discourse/components/composer-editor.js.es6
+++ b/app/assets/javascripts/discourse/components/composer-editor.js.es6
@@ -228,6 +228,8 @@ export default Ember.Component.extend({
   _bindUploadTarget() {
     this._unbindUploadTarget(); // in case it's still bound, let's clean it up first
 
+    let pasted = false;
+
     const $element = this.$();
     const csrf = this.session.get('csrfToken');
     const uploadPlaceholder = this.get('uploadPlaceholder');
@@ -238,15 +240,24 @@ export default Ember.Component.extend({
       pasteZone: $element,
     });
 
+    $element.on('fileuploadpaste', () => this.pasted = true);
+
     $element.on('fileuploadsubmit', (e, data) => {
       const isPrivateMessage = this.get("composer.privateMessage");
+
+      data.formData = { type: "composer" }
+      if (isPrivateMessage) data.formData.for_private_message = true;
+      if (this.pasted) data.formData.pasted = true;
+
       const opts = {
         isPrivateMessage,
         allowStaffToUploadAnyFileInPm: this.siteSettings.allow_staff_to_upload_any_file_in_pm,
       };
+
       const isUploading = validateUploadedFiles(data.files, opts);
-      data.formData = { type: "composer", for_private_message: isPrivateMessage };
+
       this.setProperties({ uploadProgress: 0, isUploading });
+
       return isUploading;
     });
 
@@ -255,6 +266,7 @@ export default Ember.Component.extend({
     });
 
     $element.on("fileuploadsend", (e, data) => {
+      this.pasted = false;
       this._validUploads++;
       this.appEvents.trigger('composer:insert-text', uploadPlaceholder);
 
diff --git a/app/controllers/uploads_controller.rb b/app/controllers/uploads_controller.rb
index 295671c8345..c19fa695342 100644
--- a/app/controllers/uploads_controller.rb
+++ b/app/controllers/uploads_controller.rb
@@ -13,17 +13,18 @@ class UploadsController < ApplicationController
       return render json: failed_json, status: 422
     end
 
-    url  = params[:url]
-    file = params[:file] || params[:files]&.first
-    for_private_message = params[:for_private_message]
+    url    = params[:url]
+    file   = params[:file] || params[:files]&.first
+    pasted = params[:pasted] == "true"
+    for_private_message = params[:for_private_message] == "true"
 
     if params[:synchronous] && (current_user.staff? || is_api?)
-      data = create_upload(file, url, type, for_private_message)
+      data = create_upload(file, url, type, for_private_message, pasted)
       render json: data.as_json
     else
       Scheduler::Defer.later("Create Upload") do
         begin
-          data = create_upload(file, url, type, for_private_message)
+          data = create_upload(file, url, type, for_private_message, pasted)
         ensure
           MessageBus.publish("/uploads/#{type}", (data || {}).as_json, client_ids: [params[:client_id]])
         end
@@ -60,7 +61,7 @@ class UploadsController < ApplicationController
     raise Discourse::NotFound
   end
 
-  def create_upload(file, url, type, for_private_message = false)
+  def create_upload(file, url, type, for_private_message, pasted)
     if file.nil?
       if url.present? && is_api?
         maximum_upload_size = [SiteSetting.max_image_size_kb, SiteSetting.max_attachment_size_kb].max.kilobytes
@@ -79,8 +80,12 @@ class UploadsController < ApplicationController
 
     return { errors: [I18n.t("upload.file_missing")] } if tempfile.nil?
 
-    opts = { type: type, content_type: content_type }
-    opts[:for_private_message] = true if for_private_message
+    opts = {
+      type: type,
+      content_type: content_type,
+      for_private_message: for_private_message,
+      pasted: pasted,
+    }
 
     upload = UploadCreator.new(tempfile, filename, opts).create_for(current_user.id)
 
diff --git a/lib/upload_creator.rb b/lib/upload_creator.rb
index 2e33e059e15..ddf703f6b92 100644
--- a/lib/upload_creator.rb
+++ b/lib/upload_creator.rb
@@ -19,6 +19,7 @@ class UploadCreator
   #  - for_group_message (boolean)
   #  - for_theme (boolean)
   #  - for_private_message (boolean)
+  #  - pasted (boolean)
   def initialize(file, filename, opts = {})
     @upload = Upload.new
     @file = file
@@ -121,9 +122,10 @@ class UploadCreator
   MIN_PIXELS_TO_CONVERT_TO_JPEG ||= 1280 * 720
 
   def should_convert_to_jpeg?
-    TYPES_CONVERTED_TO_JPEG.include?(@image_info.type) &&
-    pixels > MIN_PIXELS_TO_CONVERT_TO_JPEG &&
-    SiteSetting.png_to_jpg_quality < 100
+    return false if !TYPES_CONVERTED_TO_JPEG.include?(@image_info.type)
+    return true  if @opts[:pasted]
+    return false if SiteSetting.png_to_jpg_quality < 100
+    pixels > MIN_PIXELS_TO_CONVERT_TO_JPEG
   end
 
   def convert_to_jpeg!
diff --git a/spec/controllers/uploads_controller_spec.rb b/spec/controllers/uploads_controller_spec.rb
index b44436df7b2..63255e4bf2a 100644
--- a/spec/controllers/uploads_controller_spec.rb
+++ b/spec/controllers/uploads_controller_spec.rb
@@ -38,7 +38,7 @@ describe UploadsController do
       end
 
       it 'parameterize the type' do
-        subject.expects(:create_upload).with(logo, nil, "super_long_type_with_charssuper_long_type_with_char", nil)
+        subject.expects(:create_upload).with(logo, nil, "super_long_type_with_charssuper_long_type_with_char", false, false)
         xhr :post, :create, file: logo, type: "super \# long \//\\ type with \\. $%^&*( chars" * 5
       end
 
@@ -140,7 +140,7 @@ describe UploadsController do
         @user.update_columns(moderator: true)
 
         message = MessageBus.track_publish do
-          xhr :post, :create, file: text_file, type: "composer", for_private_message: true
+          xhr :post, :create, file: text_file, type: "composer", for_private_message: "true"
         end.first
 
         expect(response).to be_success