diff --git a/app/src/hid_listener.c b/app/src/hid_listener.c
index 3a11101d..796ec19b 100644
--- a/app/src/hid_listener.c
+++ b/app/src/hid_listener.c
@@ -19,6 +19,20 @@ LOG_MODULE_DECLARE(zmk, CONFIG_ZMK_LOG_LEVEL);
 static int hid_listener_keycode_pressed(const struct zmk_keycode_state_changed *ev) {
     int err, explicit_mods_changed, implicit_mods_changed;
 
+    if (zmk_hid_is_pressed(ZMK_HID_USAGE(ev->usage_page, ev->keycode))) {
+        LOG_DBG("unregistering usage_page 0x%02X keycode 0x%02X since it was already pressed",
+                ev->usage_page, ev->keycode);
+        err = zmk_hid_release(ZMK_HID_USAGE(ev->usage_page, ev->keycode));
+        if (err < 0) {
+            LOG_DBG("Unable to pre-release keycode (%d)", err);
+            return err;
+        }
+        err = zmk_endpoints_send_report(ev->usage_page);
+        if (err < 0) {
+            LOG_ERR("Failed to send key report for pre-releasing keycode (%d)", err);
+        }
+    }
+
     LOG_DBG("usage_page 0x%02X keycode 0x%02X implicit_mods 0x%02X explicit_mods 0x%02X",
             ev->usage_page, ev->keycode, ev->implicit_modifiers, ev->explicit_modifiers);
     err = zmk_hid_press(ZMK_HID_USAGE(ev->usage_page, ev->keycode));
diff --git a/app/tests/key-repeat/tap-when-rolling/events.patterns b/app/tests/key-repeat/tap-when-rolling/events.patterns
new file mode 100644
index 00000000..79471923
--- /dev/null
+++ b/app/tests/key-repeat/tap-when-rolling/events.patterns
@@ -0,0 +1,2 @@
+s/.*hid_listener_keycode_//p
+s/.*hid_implicit_modifiers_//p
\ No newline at end of file
diff --git a/app/tests/key-repeat/tap-when-rolling/keycode_events.snapshot b/app/tests/key-repeat/tap-when-rolling/keycode_events.snapshot
new file mode 100644
index 00000000..7d54e9de
--- /dev/null
+++ b/app/tests/key-repeat/tap-when-rolling/keycode_events.snapshot
@@ -0,0 +1,9 @@
+pressed: usage_page 0x07 keycode 0x04 implicit_mods 0x00 explicit_mods 0x00
+press: Modifiers set to 0x00
+pressed: unregistering usage_page 0x07 keycode 0x04 since it was already pressed
+pressed: usage_page 0x07 keycode 0x04 implicit_mods 0x00 explicit_mods 0x00
+press: Modifiers set to 0x00
+released: usage_page 0x07 keycode 0x04 implicit_mods 0x00 explicit_mods 0x00
+release: Modifiers set to 0x00
+released: usage_page 0x07 keycode 0x04 implicit_mods 0x00 explicit_mods 0x00
+release: Modifiers set to 0x00
diff --git a/app/tests/key-repeat/tap-when-rolling/native_posix.keymap b/app/tests/key-repeat/tap-when-rolling/native_posix.keymap
new file mode 100644
index 00000000..bb129d14
--- /dev/null
+++ b/app/tests/key-repeat/tap-when-rolling/native_posix.keymap
@@ -0,0 +1,13 @@
+#include <dt-bindings/zmk/keys.h>
+#include <behaviors.dtsi>
+#include <dt-bindings/zmk/kscan_mock.h>
+#include "../behavior_keymap.dtsi"
+
+&kscan {
+    events = <
+    ZMK_MOCK_PRESS(0,1,10)
+    ZMK_MOCK_PRESS(0,0,10)
+    ZMK_MOCK_RELEASE(0,1,10)
+    ZMK_MOCK_RELEASE(0,0,10)
+    >;
+};
diff --git a/app/tests/key-repeat/tap-when-rolling/native_posix_64.keymap b/app/tests/key-repeat/tap-when-rolling/native_posix_64.keymap
new file mode 100644
index 00000000..a947f7ab
--- /dev/null
+++ b/app/tests/key-repeat/tap-when-rolling/native_posix_64.keymap
@@ -0,0 +1,13 @@
+#include <dt-bindings/zmk/keys.h>
+#include <behaviors.dtsi>
+#include <dt-bindings/zmk/kscan_mock.h>
+#include "../behavior_keymap.dtsi"
+
+&kscan {
+    events = <
+    ZMK_MOCK_PRESS(0,1,9000)
+    ZMK_MOCK_PRESS(0,0,30)
+    ZMK_MOCK_RELEASE(0,1,30)
+    ZMK_MOCK_RELEASE(0,0,3000)
+    >;
+};
diff --git a/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/events.patterns b/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/events.patterns
new file mode 100644
index 00000000..cbf21aff
--- /dev/null
+++ b/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/events.patterns
@@ -0,0 +1,4 @@
+s/.*hid_listener_keycode_//p
+s/.*hid_register_mod/reg/p
+s/.*hid_unregister_mod/unreg/p
+s/.*zmk_hid_.*Modifiers set to /mods: Modifiers set to /p
\ No newline at end of file
diff --git a/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/keycode_events.snapshot b/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/keycode_events.snapshot
new file mode 100644
index 00000000..0b06bd91
--- /dev/null
+++ b/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/keycode_events.snapshot
@@ -0,0 +1,9 @@
+pressed: usage_page 0x07 keycode 0x2E implicit_mods 0x02 explicit_mods 0x00
+mods: Modifiers set to 0x02
+pressed: unregistering usage_page 0x07 keycode 0x2E since it was already pressed
+pressed: usage_page 0x07 keycode 0x2E implicit_mods 0x00 explicit_mods 0x00
+mods: Modifiers set to 0x00
+released: usage_page 0x07 keycode 0x2E implicit_mods 0x02 explicit_mods 0x00
+mods: Modifiers set to 0x00
+released: usage_page 0x07 keycode 0x2E implicit_mods 0x00 explicit_mods 0x00
+mods: Modifiers set to 0x00
diff --git a/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/native_posix_64.keymap b/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/native_posix_64.keymap
new file mode 100644
index 00000000..3926eb57
--- /dev/null
+++ b/app/tests/modifiers/implicit/kp-rolling-symbols-same-key/native_posix_64.keymap
@@ -0,0 +1,27 @@
+#include <dt-bindings/zmk/keys.h>
+#include <behaviors.dtsi>
+#include <dt-bindings/zmk/kscan_mock.h>
+
+
+&kscan {
+    events = <
+        ZMK_MOCK_PRESS(0,0,10)
+        ZMK_MOCK_PRESS(0,1,10)
+        ZMK_MOCK_RELEASE(0,0,10)
+        ZMK_MOCK_RELEASE(0,1,10)
+    >;
+};
+
+/ {
+    keymap {
+        compatible = "zmk,keymap";
+        label ="Default keymap";
+
+        default_layer {
+            bindings = <
+                &kp PLUS &kp EQUAL
+                &none &none
+            >;
+        };
+    };
+};