diff --git a/assets/javascripts/shift_key_selection.js b/assets/javascripts/shift_key_selection.js
new file mode 100644
index 0000000..2021673
--- /dev/null
+++ b/assets/javascripts/shift_key_selection.js
@@ -0,0 +1,110 @@
+$(function () {
+  let countShift = 0, shiftArray = [], optionsSelected = [];
+  $(document).on('select2:select', event => {
+    countShift = 0;
+    shiftArray = []
+    optionsSelected = [];
+  });
+  $(document).on('select2:selecting select2:unselecting', event => {
+    let target = $(event.target);
+    if (!target.attr('multiple')) {
+      return;
+    }
+    if (!event.params.args.originalEvent.shiftKey) {
+      return;
+    }
+
+    event.preventDefault();
+
+    shiftArray.push(event.params.args.data.element.index);
+    countShift++;
+
+    if (countShift < 2) {
+      return;
+    }
+
+    let [first, second] = shiftArray;
+    if (first === second) {
+      // Cancel selection when clicking on the first element
+      countShift = 0;
+      shiftArray = []
+      optionsSelected = [];
+
+      return;
+    }
+
+    if (second < first) second = [first, first = second][0]; // swap variables
+    while (second >= first) {
+      optionsSelected.push(target.children('option').eq(second).val());
+      second--;
+    }
+
+    let newItems = [];
+    if (optionsSelected.filter(o => !target.val().includes(o)).length === 0) {
+      // If all selected elements are already in the list, remove them
+      newItems = target.val().filter(o => !optionsSelected.includes(o));
+    } else {
+      // Otherwise - add everything
+      newItems = target.val().concat(optionsSelected);
+    }
+    target.val(newItems);
+
+    target.trigger('change');
+    target.select2('close');
+    target.select2('open');
+    countShift = 0;
+    shiftArray = []
+    optionsSelected = [];
+  });
+
+  // Syntax sugar for list item class
+  function option(postFix = '') {
+    let className = 'select2-results__option';
+    if (postFix.length !== 0) {
+      className += `--shift-${postFix}`;
+    }
+
+    return className;
+  }
+
+  // Click on a list item while holding down the Shift key
+  $(document).on('click', '.' + option(), event => {
+    let target = $(event.target);
+    let firstElement = target.parent().children('.' + option('first'));
+    target.parent().children().removeClass([
+      option('first'),
+      option('key-mark'),
+    ]);
+    if (event.shiftKey && !firstElement.is(target)) {
+      target.addClass(option('first'));
+    }
+  });
+
+  // Visualization of the selection of list elements that will be included in the selection
+  $(document).on('mouseover mouseout', '.' + option(), event => {
+    let target = $(event.target);
+    let firstElement = target.parent().children('.' + option('first'));
+
+    if (firstElement.length < 1) {
+      return;
+    }
+
+    target.parent().children().removeClass([
+      option('second'),
+      option('key-mark'),
+    ]);
+
+    if (!event.shiftKey) {
+      return;
+    }
+
+    target.addClass(option('second'));
+
+    let [first, second] = [firstElement.index(), target.index()];
+    if (second < first) second = [first, first = second][0]; // swap variables
+    while (second >= first) {
+      target.parent().children().eq(second).addClass(option('key-mark'));
+      second--;
+    }
+  });
+});
\ No newline at end of file
diff --git a/assets/stylesheets/searchable_selectbox.css b/assets/stylesheets/searchable_selectbox.css
index 085275c..d0ec4e9 100644
--- a/assets/stylesheets/searchable_selectbox.css
+++ b/assets/stylesheets/searchable_selectbox.css
@@ -114,3 +114,8 @@ li.select2-results__option--highlighted[role="option"][aria-selected] {
 .query-columns select[multiple] {
   min-height: 200px;
 }
+
+li.select2-results__option--shift-key-mark, li.select2-results__option--shift-first {
+  background-color: #8bbfeb !important;
+  color: white;
+}
diff --git a/lib/searchable_selectbox/hook_listener.rb b/lib/searchable_selectbox/hook_listener.rb
index 63d7b21..fae20e3 100644
--- a/lib/searchable_selectbox/hook_listener.rb
+++ b/lib/searchable_selectbox/hook_listener.rb
@@ -7,7 +7,8 @@ def view_layouts_base_html_head(context)
         stylesheet_link_tag("select2.min", :plugin => "redmine_searchable_selectbox") +
         stylesheet_link_tag("searchable_selectbox", :plugin => "redmine_searchable_selectbox") +
         javascript_include_tag("select2.full.min.js", :plugin => "redmine_searchable_selectbox") +
-        javascript_include_tag("searchable_selectbox.js", :plugin => "redmine_searchable_selectbox")
+        javascript_include_tag("searchable_selectbox.js", :plugin => "redmine_searchable_selectbox") +
+        javascript_include_tag("shift_key_selection.js", :plugin => "redmine_searchable_selectbox")
       tags += javascript_tag('var enabledMultipleSelectboxSearchable = true;') if Setting.plugin_redmine_searchable_selectbox['enabled_multiple_selectbox'].to_i == 1
       tags
     end