diff --git a/data/locale/de-DE.ini b/data/locale/de-DE.ini
index 8733e552..baf8be67 100644
--- a/data/locale/de-DE.ini
+++ b/data/locale/de-DE.ini
@@ -287,8 +287,8 @@ AdvSceneSwitcher.condition.sceneOrder.entry="Auf{{scenes}}{{sources}}{{condition
 AdvSceneSwitcher.condition.hotkey="Hotkey"
 AdvSceneSwitcher.condition.hotkey.name="Makro-Trigger-Hotkey"
 AdvSceneSwitcher.condition.hotkey.tip="Hinweis: Die Tastenkombinationen für diesen Hotkey können in den OBS-Einstellungen konfiguriert werden"
-AdvSceneSwitcher.condition.hotkey.entry.line1="Hotkey ist gedrückt"
-AdvSceneSwitcher.condition.hotkey.entry.line2="Name: {{name}}"
+AdvSceneSwitcher.condition.hotkey.entry.keyState="Hotkey ist{{keyState}}"
+AdvSceneSwitcher.condition.hotkey.entry.name="Name:{{name}}"
 AdvSceneSwitcher.condition.replay="Replay Buffer"
 AdvSceneSwitcher.condition.replay.state.stopped="Replay Buffer gestoppt"
 AdvSceneSwitcher.condition.replay.state.started="Replay Buffer gestartet"
diff --git a/data/locale/en-US.ini b/data/locale/en-US.ini
index ff5e5443..0c1164cc 100644
--- a/data/locale/en-US.ini
+++ b/data/locale/en-US.ini
@@ -482,10 +482,12 @@ AdvSceneSwitcher.condition.sceneOrder.type.position="Is at position"
 AdvSceneSwitcher.condition.sceneOrder.positionInfo="The position value starts at the bottom with 0 and increases by one for each scene item including the ones in scene groups"
 AdvSceneSwitcher.condition.sceneOrder.entry="On{{scenes}}{{sources}}{{conditions}}{{sources2}}{{position}}"
 AdvSceneSwitcher.condition.hotkey="Hotkey"
+AdvSceneSwitcher.condition.hotkey.pressed="pressed"
+AdvSceneSwitcher.condition.hotkey.released="released"
 AdvSceneSwitcher.condition.hotkey.name="Macro trigger hotkey"
 AdvSceneSwitcher.condition.hotkey.tip="Note: You can configure the keybindings for this hotkey in the OBS settings window"
-AdvSceneSwitcher.condition.hotkey.entry.line1="Hotkey is pressed"
-AdvSceneSwitcher.condition.hotkey.entry.line2="Name:{{name}}"
+AdvSceneSwitcher.condition.hotkey.entry.keyState="Hotkey is{{keyState}}"
+AdvSceneSwitcher.condition.hotkey.entry.name="Name:{{name}}"
 AdvSceneSwitcher.condition.replay="Replay buffer"
 AdvSceneSwitcher.condition.replay.state.stopped="Replay buffer stopped"
 AdvSceneSwitcher.condition.replay.state.started="Replay buffer started"
diff --git a/data/locale/es-ES.ini b/data/locale/es-ES.ini
index d16fdb79..fd60f033 100644
--- a/data/locale/es-ES.ini
+++ b/data/locale/es-ES.ini
@@ -238,8 +238,7 @@ AdvSceneSwitcher.condition.sceneOrder.entry="En{{scenes}}{{sources}}{{conditions
 AdvSceneSwitcher.condition.hotkey="Tecla de acceso rápido"
 AdvSceneSwitcher.condition.hotkey.name="Tecla de acceso directo de activación de macro"
 AdvSceneSwitcher.condition.hotkey.tip="Nota: puede configurar las combinaciones de teclas para esta tecla de acceso rápido en la ventana de configuración de OBS"
-AdvSceneSwitcher.condition.hotkey.entry.line1="Se presiona la tecla de acceso rápido"
-AdvSceneSwitcher.condition.hotkey.entry.line2="Nombre: {{name}}"
+AdvSceneSwitcher.condition.hotkey.entry.name="Nombre:{{name}}"
 AdvSceneSwitcher.condition.replay="Búfer de reproducción"
 AdvSceneSwitcher.condition.replay.state.stopped="Búfer de reproducción detenido"
 AdvSceneSwitcher.condition.replay.state.started="Búfer de reproducción iniciado"
diff --git a/data/locale/fr-FR.ini b/data/locale/fr-FR.ini
index df2b4e8a..ce30e3b5 100644
--- a/data/locale/fr-FR.ini
+++ b/data/locale/fr-FR.ini
@@ -351,8 +351,7 @@ AdvSceneSwitcher.condition.sceneOrder.entry="Sur{{scenes}}{{sources}}{{condition
 AdvSceneSwitcher.condition.hotkey="Raccourci clavier"
 AdvSceneSwitcher.condition.hotkey.name="Raccourci clavier de déclenchement de macro"
 AdvSceneSwitcher.condition.hotkey.tip="Remarque : Vous pouvez configurer les raccourcis clavier pour ce raccourci dans la fenêtre de paramètres d'OBS"
-AdvSceneSwitcher.condition.hotkey.entry.line1="Raccourci clavier est enfoncé"
-AdvSceneSwitcher.condition.hotkey.entry.line2="Nom :{{name}}"
+AdvSceneSwitcher.condition.hotkey.entry.name="Nom:{{name}}"
 AdvSceneSwitcher.condition.replay="Tampon de répétition"
 AdvSceneSwitcher.condition.replay.state.stopped="Tampon de répétition arrêté"
 AdvSceneSwitcher.condition.replay.state.started="Tampon de répétition démarré"
diff --git a/data/locale/zh-CN.ini b/data/locale/zh-CN.ini
index 56f8bdaf..4fa4fa1e 100644
--- a/data/locale/zh-CN.ini
+++ b/data/locale/zh-CN.ini
@@ -332,8 +332,7 @@ AdvSceneSwitcher.condition.sceneOrder.entry="在 {{scenes}} {{sources}} {{condit
 AdvSceneSwitcher.condition.hotkey="热键"
 AdvSceneSwitcher.condition.hotkey.name="宏触发热键"
 AdvSceneSwitcher.condition.hotkey.tip="注意：您可以在OBS设置窗口中为此热键配置按键绑定"
-AdvSceneSwitcher.condition.hotkey.entry.line1="热键被按下"
-AdvSceneSwitcher.condition.hotkey.entry.line2="名称: {{name}}"
+AdvSceneSwitcher.condition.hotkey.entry.name="名称:{{name}}"
 AdvSceneSwitcher.condition.replay="回放缓存"
 AdvSceneSwitcher.condition.replay.state.stopped="回放缓存已停止"
 AdvSceneSwitcher.condition.replay.state.started="回放缓存已启动"
diff --git a/plugins/base/macro-condition-hotkey.cpp b/plugins/base/macro-condition-hotkey.cpp
index b145a85e..26cd03f2 100644
--- a/plugins/base/macro-condition-hotkey.cpp
+++ b/plugins/base/macro-condition-hotkey.cpp
@@ -23,13 +23,17 @@ MacroConditionHotkey::MacroConditionHotkey(Macro *m) : MacroCondition(m)
 
 bool MacroConditionHotkey::CheckCondition()
 {
-	const bool hotkeyIsCurrentlyPressed = _hotkey->GetPressed();
-	const bool hotkeyWasPressedSinceLastCheck = _hotkey->GetLastPressed() >
-						    _lastCheck;
+	const bool keyStateCurrentlyMatches =
+		_checkPressed ? _hotkey->GetPressed() : !_hotkey->GetPressed();
+	const auto lastKeyStateMatch = _checkPressed
+					       ? _hotkey->GetLastPressed()
+					       : _hotkey->GetLastReleased();
+	const bool hotkeySateChangedSinceLastCheck = lastKeyStateMatch >
+						     _lastCheck;
 	const bool macroWasPausedSinceLastCheck =
 		MacroWasPausedSince(GetMacro(), _lastCheck);
-	bool ret = hotkeyIsCurrentlyPressed ||
-		   (hotkeyWasPressedSinceLastCheck &&
+	bool ret = keyStateCurrentlyMatches ||
+		   (hotkeySateChangedSinceLastCheck &&
 		    !macroWasPausedSinceLastCheck);
 	_lastCheck = std::chrono::high_resolution_clock::now();
 	return ret;
@@ -39,6 +43,7 @@ bool MacroConditionHotkey::Save(obs_data_t *obj) const
 {
 	MacroCondition::Save(obj);
 	_hotkey->Save(obj);
+	obs_data_set_bool(obj, "checkPressed", _checkPressed);
 	return true;
 }
 
@@ -52,34 +57,47 @@ bool MacroConditionHotkey::Load(obs_data_t *obj)
 		      "hotkey name conflict for \"%s\" - using previous key bind",
 		      description);
 	}
+	if (obs_data_has_user_value(obj, "checkPressed")) {
+		_checkPressed = obs_data_get_bool(obj, "checkPressed");
+	} else { // TODO: Remove fallback at some point in the future
+		_checkPressed = true;
+	}
 	return true;
 }
 
 MacroConditionHotkeyEdit::MacroConditionHotkeyEdit(
 	QWidget *parent, std::shared_ptr<MacroConditionHotkey> entryData)
-	: QWidget(parent)
+	: QWidget(parent),
+	  _name(new QLineEdit()),
+	  _keyState(new QComboBox())
 {
-	_name = new QLineEdit();
-	QLabel *line1 = new QLabel(obs_module_text(
-		"AdvSceneSwitcher.condition.hotkey.entry.line1"));
-	QLabel *hint = new QLabel(
-		obs_module_text("AdvSceneSwitcher.condition.hotkey.tip"));
+	_keyState->addItems(
+		QStringList()
+		<< obs_module_text("AdvSceneSwitcher.condition.hotkey.pressed")
+		<< obs_module_text(
+			   "AdvSceneSwitcher.condition.hotkey.released"));
 
 	QWidget::connect(_name, SIGNAL(editingFinished()), this,
 			 SLOT(NameChanged()));
+	QWidget::connect(_keyState, SIGNAL(currentIndexChanged(int)), this,
+			 SLOT(KeyStateChanged(int)));
 
-	QHBoxLayout *switchLayout = new QHBoxLayout;
-	std::unordered_map<std::string, QWidget *> widgetPlaceholders = {
-		{"{{name}}", _name},
-	};
-	PlaceWidgets(obs_module_text(
-			     "AdvSceneSwitcher.condition.hotkey.entry.line2"),
-		     switchLayout, widgetPlaceholders);
+	auto keyStateLayout = new QHBoxLayout;
+	PlaceWidgets(
+		obs_module_text(
+			"AdvSceneSwitcher.condition.hotkey.entry.keyState"),
+		keyStateLayout, {{"{{keyState}}", _keyState}});
 
-	QVBoxLayout *mainLayout = new QVBoxLayout;
-	mainLayout->addWidget(line1);
-	mainLayout->addLayout(switchLayout);
-	mainLayout->addWidget(hint);
+	auto nameLayout = new QHBoxLayout;
+	PlaceWidgets(
+		obs_module_text("AdvSceneSwitcher.condition.hotkey.entry.name"),
+		nameLayout, {{"{{name}}", _name}});
+
+	auto mainLayout = new QVBoxLayout;
+	mainLayout->addLayout(keyStateLayout);
+	mainLayout->addLayout(nameLayout);
+	mainLayout->addWidget(new QLabel(
+		obs_module_text("AdvSceneSwitcher.condition.hotkey.tip")));
 	setLayout(mainLayout);
 
 	_entryData = entryData;
@@ -116,6 +134,17 @@ void MacroConditionHotkeyEdit::UpdateEntryData()
 
 	_name->setText(
 		QString::fromStdString(_entryData->_hotkey->GetDescription()));
+	_keyState->setCurrentIndex(_entryData->_checkPressed ? 0 : 1);
+}
+
+void MacroConditionHotkeyEdit::KeyStateChanged(int index)
+{
+	if (_loading || !_entryData) {
+		return;
+	}
+
+	auto lock = LockContext();
+	_entryData->_checkPressed = index == 0;
 }
 
 } // namespace advss
diff --git a/plugins/base/macro-condition-hotkey.hpp b/plugins/base/macro-condition-hotkey.hpp
index 7f817248..f31164f6 100644
--- a/plugins/base/macro-condition-hotkey.hpp
+++ b/plugins/base/macro-condition-hotkey.hpp
@@ -20,6 +20,7 @@ public:
 	}
 
 	std::shared_ptr<Hotkey> _hotkey;
+	bool _checkPressed = true;
 
 private:
 	std::chrono::high_resolution_clock::time_point _lastCheck{};
@@ -46,12 +47,12 @@ public:
 
 private slots:
 	void NameChanged();
-
-protected:
-	QLineEdit *_name;
-	std::shared_ptr<MacroConditionHotkey> _entryData;
+	void KeyStateChanged(int);
 
 private:
+	QLineEdit *_name;
+	QComboBox *_keyState;
+	std::shared_ptr<MacroConditionHotkey> _entryData;
 	bool _loading = true;
 };
 
diff --git a/plugins/base/utils/hotkey-helpers.cpp b/plugins/base/utils/hotkey-helpers.cpp
index 41874196..5563d0c6 100644
--- a/plugins/base/utils/hotkey-helpers.cpp
+++ b/plugins/base/utils/hotkey-helpers.cpp
@@ -116,6 +116,9 @@ void Hotkey::Callback(void *data, obs_hotkey_id, obs_hotkey_t *, bool pressed)
 	if (pressed) {
 		hotkey->_lastPressed =
 			std::chrono::high_resolution_clock::now();
+	} else {
+		hotkey->_lastReleased =
+			std::chrono::high_resolution_clock::now();
 	}
 	hotkey->_pressed = pressed;
 }
diff --git a/plugins/base/utils/hotkey-helpers.hpp b/plugins/base/utils/hotkey-helpers.hpp
index efbbded2..cd55df21 100644
--- a/plugins/base/utils/hotkey-helpers.hpp
+++ b/plugins/base/utils/hotkey-helpers.hpp
@@ -27,6 +27,7 @@ public:
 
 	bool GetPressed() const { return _pressed; }
 	auto GetLastPressed() const { return _lastPressed; }
+	auto GetLastReleased() const { return _lastReleased; }
 	std::string GetDescription() const { return _description; }
 	bool UpdateDescription(const std::string &);
 
@@ -43,6 +44,7 @@ private:
 	obs_hotkey_id _hotkeyID = OBS_INVALID_HOTKEY_ID;
 	bool _pressed = false;
 	std::chrono::high_resolution_clock::time_point _lastPressed{};
+	std::chrono::high_resolution_clock::time_point _lastReleased{};
 	// When set will not attempt to share settings with existing hotkey
 	bool _ignoreExistingHotkeys = false;
 };