diff --git a/src/main/java/org/cryptomator/ui/addvaultwizard/ChooseExistingVaultController.java b/src/main/java/org/cryptomator/ui/addvaultwizard/ChooseExistingVaultController.java
index 432007c99..50cbb73e0 100644
--- a/src/main/java/org/cryptomator/ui/addvaultwizard/ChooseExistingVaultController.java
+++ b/src/main/java/org/cryptomator/ui/addvaultwizard/ChooseExistingVaultController.java
@@ -2,10 +2,15 @@ package org.cryptomator.ui.addvaultwizard;
 
 import dagger.Lazy;
 import org.apache.commons.lang3.SystemUtils;
+import org.cryptomator.common.LicenseHolder;
 import org.cryptomator.common.settings.Settings;
 import org.cryptomator.common.settings.UiTheme;
 import org.cryptomator.common.vaults.Vault;
 import org.cryptomator.common.vaults.VaultListManager;
+import org.cryptomator.integrations.uiappearance.Theme;
+import org.cryptomator.integrations.uiappearance.UiAppearanceException;
+import org.cryptomator.integrations.uiappearance.UiAppearanceListener;
+import org.cryptomator.integrations.uiappearance.UiAppearanceProvider;
 import org.cryptomator.ui.common.FxController;
 import org.cryptomator.ui.common.FxmlFile;
 import org.cryptomator.ui.common.FxmlScene;
@@ -15,6 +20,8 @@ import org.slf4j.LoggerFactory;
 
 import javax.inject.Inject;
 import javafx.beans.property.ObjectProperty;
+import javafx.beans.property.SimpleObjectProperty;
+import javafx.beans.value.ObservableValue;
 import javafx.fxml.FXML;
 import javafx.scene.Scene;
 import javafx.scene.image.Image;
@@ -23,6 +30,7 @@ import javafx.stage.Stage;
 import java.io.File;
 import java.io.IOException;
 import java.nio.file.Path;
+import java.util.Optional;
 import java.util.ResourceBundle;
 
 import static org.cryptomator.common.Constants.CRYPTOMATOR_FILENAME_GLOB;
@@ -41,11 +49,14 @@ public class ChooseExistingVaultController implements FxController {
 	private final VaultListManager vaultListManager;
 	private final ResourceBundle resourceBundle;
 	private final Settings settings;
+	private final Optional<UiAppearanceProvider> appearanceProvider;
+	private final LicenseHolder licenseHolder;
+	private final UiAppearanceListener systemInterfaceThemeListener = this::systemInterfaceThemeChanged;
 
-	private Image screenshot;
+	private final ObjectProperty<Image> screenshot = new SimpleObjectProperty<>();
 
 	@Inject
-	ChooseExistingVaultController(@AddVaultWizardWindow Stage window, @FxmlScene(FxmlFile.ADDVAULT_WELCOME) Lazy<Scene> welcomeScene, @FxmlScene(FxmlFile.ADDVAULT_SUCCESS) Lazy<Scene> successScene, FxApplicationWindows appWindows, ObjectProperty<Path> vaultPath, @AddVaultWizardWindow ObjectProperty<Vault> vault, VaultListManager vaultListManager, ResourceBundle resourceBundle, Settings settings) {
+	ChooseExistingVaultController(@AddVaultWizardWindow Stage window, @FxmlScene(FxmlFile.ADDVAULT_WELCOME) Lazy<Scene> welcomeScene, @FxmlScene(FxmlFile.ADDVAULT_SUCCESS) Lazy<Scene> successScene, FxApplicationWindows appWindows, ObjectProperty<Path> vaultPath, @AddVaultWizardWindow ObjectProperty<Vault> vault, VaultListManager vaultListManager, ResourceBundle resourceBundle, Settings settings, Optional<UiAppearanceProvider> appearanceProvider, LicenseHolder licenseHolder) {
 		this.window = window;
 		this.welcomeScene = welcomeScene;
 		this.successScene = successScene;
@@ -55,17 +66,73 @@ public class ChooseExistingVaultController implements FxController {
 		this.vaultListManager = vaultListManager;
 		this.resourceBundle = resourceBundle;
 		this.settings = settings;
+		this.appearanceProvider = appearanceProvider;
+		this.licenseHolder = licenseHolder;
 	}
 
 	@FXML
 	public void initialize() {
 		if (SystemUtils.IS_OS_MAC) {
-			this.screenshot = new Image(getClass().getResource("/img/select-masterkey-mac"+(UiTheme.LIGHT == settings.theme().get()? "":"-dark")+".png").toString());
+			settings.theme().addListener(this::appThemeChanged);
+			setSelectedMacScreenshot(settings.theme().get());
 		} else {
-			this.screenshot = new Image(getClass().getResource("/img/select-masterkey-win.png").toString());
+			this.screenshot.set(new Image(getClass().getResource("/img/select-masterkey-win.png").toString()));
 		}
 	}
 
+	private void appThemeChanged(@SuppressWarnings("unused") ObservableValue<? extends UiTheme> observable, @SuppressWarnings("unused") UiTheme oldValue, UiTheme newValue) {
+		if (appearanceProvider.isPresent() && oldValue == UiTheme.AUTOMATIC && newValue != UiTheme.AUTOMATIC) {
+			try {
+				appearanceProvider.get().removeListener(systemInterfaceThemeListener);
+			} catch (UiAppearanceException e) {
+				LOG.error("Failed to disable automatic theme switching.");
+			}
+		}
+		setSelectedMacScreenshot(newValue);
+	}
+
+	private void setSelectedMacScreenshot(UiTheme desiredTheme) {
+		UiTheme theme = licenseHolder.isValidLicense() ? desiredTheme : UiTheme.LIGHT;
+		switch (theme) {
+			case LIGHT -> setLightMacScreenshot();
+			case DARK -> setDarkMacScreenshot();
+			case AUTOMATIC -> {
+				appearanceProvider.ifPresent(provider -> {
+					try {
+						provider.addListener(systemInterfaceThemeListener);
+					} catch (UiAppearanceException e) {
+						LOG.error("Failed to enable automatic theme switching.");
+					}
+				});
+				setSystemMacScreenshot();
+			}
+		}
+	}
+
+	private void systemInterfaceThemeChanged(Theme theme) {
+		switch (theme) {
+			case LIGHT -> setLightMacScreenshot();
+			case DARK -> setDarkMacScreenshot();
+		}
+	}
+
+	private void setSystemMacScreenshot() {
+		if (appearanceProvider.isPresent()) {
+			systemInterfaceThemeChanged(appearanceProvider.get().getSystemTheme());
+		} else {
+			LOG.warn("No UiAppearanceProvider present, assuming LIGHT theme...");
+			setLightMacScreenshot();
+		}
+	}
+
+	private void setLightMacScreenshot() {
+		this.screenshot.set(new Image(getClass().getResource("/img/select-masterkey-mac.png").toString()));
+	}
+
+	private void setDarkMacScreenshot() {
+		this.screenshot.set(new Image(getClass().getResource("/img/select-masterkey-mac-dark.png").toString()));
+	}
+
 	@FXML
 	public void back() {
 		window.setScene(welcomeScene.get());
@@ -92,8 +159,13 @@ public class ChooseExistingVaultController implements FxController {
 
 	/* Getter */
 
-	public Image getScreenshot() {
+	public ObjectProperty<Image> screenshotProperty() {
 		return screenshot;
 	}
 
+	public Image getScreenshot() {
+		return screenshot.get();
+	}
+
+
 }