diff --git a/src/modules/keyboardmanager/KeyboardManagerEngineLibrary/KeyboardEventHandlers.cpp b/src/modules/keyboardmanager/KeyboardManagerEngineLibrary/KeyboardEventHandlers.cpp
index e401b849f0..89ab272c93 100644
--- a/src/modules/keyboardmanager/KeyboardManagerEngineLibrary/KeyboardEventHandlers.cpp
+++ b/src/modules/keyboardmanager/KeyboardManagerEngineLibrary/KeyboardEventHandlers.cpp
@@ -586,22 +586,36 @@ namespace KeyboardEventHandlers
                                 if (newRemapping.RemapToKey())
                                 {
                                     DWORD to = std::get<0>(newRemapping.targetShortcut);
-                                    key_count = from.Size() - 1 + 1;
+                                    bool isLastKeyStillPressed = ii.GetVirtualKeyState((WORD)from.actionKey);
+                                    key_count = from.Size() - 1 + 1 + (isLastKeyStillPressed ? 1 : 0);
                                     keyEventList = new INPUT[key_count]();
                                     memset(keyEventList, 0, sizeof(keyEventList));
                                     int i = 0;
                                     Helpers::SetModifierKeyEvents(from, it->second.winKeyInvoked, keyEventList, i, false, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG);
+                                    if (ii.GetVirtualKeyState((WORD)from.actionKey))
+                                    {
+                                        // If the action key from the last shortcut is still being pressed, release it.
+                                        Helpers::SetKeyEvent(keyEventList, i, INPUT_KEYBOARD, (WORD)from.actionKey, KEYEVENTF_KEYUP, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG);
+                                        i++;
+                                    }
                                     Helpers::SetKeyEvent(keyEventList, i, INPUT_KEYBOARD, (WORD)to, 0, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG);
                                 }else
                                 {
                                     Shortcut to = std::get<Shortcut>(newRemapping.targetShortcut);
-                                    key_count = from.Size() - 1 + to.Size() - 1 - 2* from.GetCommonModifiersCount(to) + 1;
+                                    bool isLastKeyStillPressed = ii.GetVirtualKeyState((WORD)from.actionKey);
+
+                                    key_count = from.Size() - 1 + to.Size() - 1 - 2* from.GetCommonModifiersCount(to) + 1 + (isLastKeyStillPressed ? 1 : 0);
                                     keyEventList = new INPUT[key_count]();
 
                                     int i = 0;
                                     Helpers::SetModifierKeyEvents(from, it->second.winKeyInvoked, keyEventList, i, false, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG, to);
+                                    if (ii.GetVirtualKeyState((WORD)from.actionKey))
+                                    {
+                                        // If the action key from the last shortcut is still being pressed, release it.
+                                        Helpers::SetKeyEvent(keyEventList, i, INPUT_KEYBOARD, (WORD)from.actionKey, KEYEVENTF_KEYUP, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG);
+                                        i++;
+                                    }
                                     Helpers::SetModifierKeyEvents(to, it->second.winKeyInvoked, keyEventList, i, true, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG, from);
-
                                     Helpers::SetKeyEvent(keyEventList, i, INPUT_KEYBOARD, (WORD)to.actionKey, 0, KeyboardManagerConstants::KEYBOARDMANAGER_SHORTCUT_FLAG);
                                     newRemapping.isShortcutInvoked = true;
                                 }