diff --git a/tests/features/rollover/common.h b/tests/features/rollover/common.h
new file mode 100644
index 00000000..dcfcc35b
--- /dev/null
+++ b/tests/features/rollover/common.h
@@ -0,0 +1,27 @@
+// -*- mode: c++ -*-
+
+/* Kaleidoscope - Firmware for computer input devices
+ * Copyright (C) 2020  Keyboard.io, Inc.
+ *
+ * This program is free software: you can redistribute it and/or modify it under
+ * the terms of the GNU General Public License as published by the Free Software
+ * Foundation, version 3.
+ *
+ * This program is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS
+ * FOR A PARTICULAR PURPOSE. See the GNU General Public License for more
+ * details.
+ *
+ * You should have received a copy of the GNU General Public License along with
+ * this program. If not, see <http://www.gnu.org/licenses/>.
+ */
+
+#pragma once
+
+#include <cstdint>
+
+namespace kaleidoscope {
+namespace testing {
+
+}  // namespace testing
+}  // namespace kaleidoscope
diff --git a/tests/features/rollover/rollover.ino b/tests/features/rollover/rollover.ino
new file mode 100644
index 00000000..e474f49c
--- /dev/null
+++ b/tests/features/rollover/rollover.ino
@@ -0,0 +1,48 @@
+/* -*- mode: c++ -*-
+ * Copyright (C) 2020  Keyboard.io, Inc.
+ *
+ * This program is free software: you can redistribute it and/or modify it under
+ * the terms of the GNU General Public License as published by the Free Software
+ * Foundation, version 3.
+ *
+ * This program is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS
+ * FOR A PARTICULAR PURPOSE. See the GNU General Public License for more
+ * details.
+ *
+ * You should have received a copy of the GNU General Public License along with
+ * this program. If not, see <http://www.gnu.org/licenses/>.
+ */
+
+#include <Kaleidoscope.h>
+
+#include "./common.h"
+
+// *INDENT-OFF*
+KEYMAPS(
+    [0] = KEYMAP_STACKED
+    (
+        LSHIFT(Key_A), LSHIFT(Key_B), LSHIFT(LCTRL(LALT(Key_X))), ___, ___, ___, ___,
+        Key_A, Key_B, ___, ___, ___, ___, ___,
+        Key_LeftShift, Key_RightShift, ___, ___, ___, ___,
+        ___, ___, ___, ___, ___, ___, ___,
+        ___, ___, ___, ___,
+        ___,
+
+        ___, ___, ___, ___, ___, ___, ___,
+        ___, ___, ___, ___, ___, ___, ___,
+        ___, ___, ___, ___, ___, ___,
+        ___, ___, ___, ___, ___, ___, ___,
+        ___, ___, ___, ___,
+        ___
+    ),
+)
+// *INDENT-ON*
+
+void setup() {
+  Kaleidoscope.setup();
+}
+
+void loop() {
+  Kaleidoscope.loop();
+}
diff --git a/tests/features/rollover/sketch.json b/tests/features/rollover/sketch.json
new file mode 100644
index 00000000..43dc4c7e
--- /dev/null
+++ b/tests/features/rollover/sketch.json
@@ -0,0 +1,6 @@
+{
+  "cpu": {
+    "fqbn": "keyboardio:virtual:model01",
+    "port": ""
+  }
+}
\ No newline at end of file
diff --git a/tests/features/rollover/test.ktest b/tests/features/rollover/test.ktest
new file mode 100644
index 00000000..43f911ba
--- /dev/null
+++ b/tests/features/rollover/test.ktest
@@ -0,0 +1,70 @@
+VERSION 1
+
+KEYSWITCH SFT_A  0 0
+KEYSWITCH SFT_B  0 1
+KEYSWITCH MEH_X  0 2
+KEYSWITCH A      1 0
+KEYSWITCH B      1 1
+KEYSWITCH LSFT   2 0
+KEYSWITCH RSFT   2 1
+
+# ==============================================================================
+NAME Key with modifier flag alone
+
+RUN 4 ms
+PRESS SFT_A
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift # The report should contain `shift`
+EXPECT keyboard-report Key_LeftShift Key_A # The report should contain `shift` + `A`
+
+RUN 4 ms
+RELEASE SFT_A
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift # The report should contain `shift`
+EXPECT keyboard-report empty # Report should be empty
+
+RUN 5 ms
+
+# ==============================================================================
+NAME Key with multiple modifier flags alone
+
+RUN 4 ms
+PRESS MEH_X
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift Key_LeftControl Key_LeftAlt # The report should contain three modifiers
+EXPECT keyboard-report Key_LeftShift Key_LeftControl Key_LeftAlt Key_X # The report should add `X`
+
+RUN 4 ms
+RELEASE MEH_X
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift Key_LeftControl Key_LeftAlt # The report should contain three modifiers
+EXPECT keyboard-report empty # Report should be empty
+
+RUN 5 ms
+
+# ==============================================================================
+NAME No mod flags to mod flags
+
+RUN 4 ms
+PRESS A
+RUN 1 cycle
+EXPECT keyboard-report Key_A # The report should contain `A`
+
+RUN 4 ms
+PRESS SFT_B
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift Key_A # The report should contain `shift` + `A`
+EXPECT keyboard-report Key_LeftShift Key_A Key_B # The report should contain `shift`, `A` & `B`
+
+RUN 4 ms
+RELEASE A
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift Key_B # The report should contain `shift` + `B`
+
+RUN 4 ms
+RELEASE SFT_B
+RUN 1 cycle
+EXPECT keyboard-report Key_LeftShift # The report should contain `shift`
+EXPECT keyboard-report empty # Report should be empty
+
+RUN 5 ms