diff --git a/lib/bootstrap_form/helpers/bootstrap.rb b/lib/bootstrap_form/helpers/bootstrap.rb
index 7f3d7d3f..d5c62749 100644
--- a/lib/bootstrap_form/helpers/bootstrap.rb
+++ b/lib/bootstrap_form/helpers/bootstrap.rb
@@ -75,9 +75,10 @@ def prepend_and_append_input(name, options, &)
         input = capture(&) || ActiveSupport::SafeBuffer.new
 
         input = attach_input(options, :prepend) + input + attach_input(options, :append)
-        input << generate_error(name, id)
+        error = generate_error(name, id)
+        input << error
         options.present? &&
-          input = tag.div(input, class: ["input-group", options[:input_group_class]].compact)
+          input = tag.div(input, class: ["input-group", ("has-validation" if error), options[:input_group_class]].compact)
         input
       end
 
diff --git a/test/bootstrap_form_group_test.rb b/test/bootstrap_form_group_test.rb
index acc9d102..e844279d 100644
--- a/test/bootstrap_form_group_test.rb
+++ b/test/bootstrap_form_group_test.rb
@@ -195,7 +195,7 @@ class BootstrapFormGroupTest < ActionView::TestCase
       <form accept-charset="UTF-8" action="/users" class="new_user" id="new_user" method="post">
         <div class="mb-3">
           <label class="form-label required" for="user_email">Email</label>
-          <div class="input-group">
+          <div class="input-group has-validation">
             <span class="input-group-text">$</span>
             <input required="required" class="form-control is-invalid" id="user_email" aria-describedby="user_email_feedback" name="user[email]" type="text" />
             <span class="input-group-text">.00</span>
@@ -207,6 +207,24 @@ class BootstrapFormGroupTest < ActionView::TestCase
     assert_equivalent_html expected, bootstrap_form_for(@user) { |f| f.text_field :email, prepend: "$", append: ".00" }
   end
 
+  test "adding prepend text with validation error and inline errors turned off" do
+    @user.email = nil
+    assert @user.invalid?
+
+    expected = <<~HTML
+      <form accept-charset="UTF-8" action="/users" class="new_user" id="new_user" method="post">
+        <div class="mb-3">
+          <label class="form-label required" for="user_email">Email</label>
+          <div class="input-group">
+            <span class="input-group-text">$</span>
+            <input required="required" class="form-control is-invalid" id="user_email" aria-describedby="user_email_feedback" name="user[email]" type="text" />
+          </div>
+        </div>
+      </form>
+    HTML
+    assert_equivalent_html expected, bootstrap_form_for(@user, inline_errors: false) { |f| f.text_field :email, prepend: "$" }
+  end
+
   test "file field with prepend text" do
     expected = <<~HTML
       <div class="mb-3">