diff --git a/core/src/main/resources/i18n/displayStrings.properties b/core/src/main/resources/i18n/displayStrings.properties
index 364c43105c..c2afe21cb8 100644
--- a/core/src/main/resources/i18n/displayStrings.properties
+++ b/core/src/main/resources/i18n/displayStrings.properties
@@ -2691,7 +2691,7 @@ displayUpdateDownloadWindow.verify.failed=Verification failed.\n\
   Please download and verify manually at [HYPERLINK:https://bisq.network/downloads]
 displayUpdateDownloadWindow.success=The new version has been successfully downloaded and the signature verified.\n\n\
 Please open the download directory, shut down the application and install the new version.
-displayUpdateDownloadWindow.download.openDir=Open download directory
+displayUpdateDownloadWindow.download.openDir=Open download directory and shut down
 
 disputeSummaryWindow.title=Summary
 disputeSummaryWindow.openDate=Ticket opening date
diff --git a/desktop/src/main/java/bisq/desktop/app/BisqAppMain.java b/desktop/src/main/java/bisq/desktop/app/BisqAppMain.java
index a875e83ca6..3d2628cdad 100644
--- a/desktop/src/main/java/bisq/desktop/app/BisqAppMain.java
+++ b/desktop/src/main/java/bisq/desktop/app/BisqAppMain.java
@@ -23,6 +23,10 @@ import bisq.desktop.setup.DesktopPersistedDataHost;
 
 import bisq.core.app.AvoidStandbyModeService;
 import bisq.core.app.BisqExecutable;
+import bisq.core.app.TorSetup;
+import bisq.core.user.Cookie;
+import bisq.core.user.CookieKey;
+import bisq.core.user.User;
 
 import bisq.common.UserThread;
 import bisq.common.app.AppModule;
@@ -125,6 +129,16 @@ public class BisqAppMain extends BisqExecutable {
 
     @Override
     protected void startApplication() {
+        Cookie cookie = injector.getInstance(User.class).getCookie();
+        cookie.getAsOptionalBoolean(CookieKey.CLEAN_TOR_DIR_AT_RESTART).ifPresent(wasCleanTorDirSet -> {
+            if (wasCleanTorDirSet) {
+                injector.getInstance(TorSetup.class).cleanupTorFiles(() -> {
+                    log.info("Tor directory reset");
+                    cookie.remove(CookieKey.CLEAN_TOR_DIR_AT_RESTART);
+                }, log::error);
+            }
+        });
+
         // We need to be in user thread! We mapped at launchApplication already.  Once
         // the UI is ready we get onApplicationStarted called and start the setup there.
         application.startApplication(this::onApplicationStarted);
diff --git a/desktop/src/main/java/bisq/desktop/main/MainViewModel.java b/desktop/src/main/java/bisq/desktop/main/MainViewModel.java
index c4a1102054..8f7d0fc4f1 100644
--- a/desktop/src/main/java/bisq/desktop/main/MainViewModel.java
+++ b/desktop/src/main/java/bisq/desktop/main/MainViewModel.java
@@ -411,7 +411,7 @@ public class MainViewModel implements ViewModel, BisqSetup.BisqSetupListener {
                 .onClose(() -> BisqApp.getShutDownHandler().run())
                 .show());
 
-        bisqSetup.setDisplayUpdateHandler((alert, key) -> new DisplayUpdateDownloadWindow(alert, config)
+        bisqSetup.setDisplayUpdateHandler((alert, key) -> new DisplayUpdateDownloadWindow(alert, config, user)
                 .actionButtonText(Res.get("displayUpdateDownloadWindow.button.downloadLater"))
                 .onAction(() -> {
                     preferences.dontShowAgain(key, false); // update later
diff --git a/desktop/src/main/java/bisq/desktop/main/overlays/windows/downloadupdate/DisplayUpdateDownloadWindow.java b/desktop/src/main/java/bisq/desktop/main/overlays/windows/downloadupdate/DisplayUpdateDownloadWindow.java
index 1a2015fe95..f6994b0232 100644
--- a/desktop/src/main/java/bisq/desktop/main/overlays/windows/downloadupdate/DisplayUpdateDownloadWindow.java
+++ b/desktop/src/main/java/bisq/desktop/main/overlays/windows/downloadupdate/DisplayUpdateDownloadWindow.java
@@ -17,6 +17,7 @@
 
 package bisq.desktop.main.overlays.windows.downloadupdate;
 
+import bisq.desktop.app.BisqApp;
 import bisq.desktop.components.AutoTooltipButton;
 import bisq.desktop.components.AutoTooltipLabel;
 import bisq.desktop.components.BusyAnimation;
@@ -25,7 +26,10 @@ import bisq.desktop.main.overlays.popups.Popup;
 
 import bisq.core.alert.Alert;
 import bisq.core.locale.Res;
+import bisq.core.user.CookieKey;
+import bisq.core.user.User;
 
+import bisq.common.UserThread;
 import bisq.common.config.Config;
 import bisq.common.util.Utilities;
 
@@ -72,6 +76,7 @@ import static com.google.common.base.Preconditions.checkNotNull;
 public class DisplayUpdateDownloadWindow extends Overlay<DisplayUpdateDownloadWindow> {
     private final Alert alert;
     private final Config config;
+    private final User user;
     private Optional<DownloadTask> downloadTaskOptional;
     private VerifyTask verifyTask;
     private ProgressBar progressBar;
@@ -82,9 +87,10 @@ public class DisplayUpdateDownloadWindow extends Overlay<DisplayUpdateDownloadWi
     // Public API
     ///////////////////////////////////////////////////////////////////////////////////////////
 
-    public DisplayUpdateDownloadWindow(Alert alert, Config config) {
+    public DisplayUpdateDownloadWindow(Alert alert, Config config, User user) {
         this.alert = alert;
         this.config = config;
+        this.user = user;
         this.type = Type.Attention;
     }
 
@@ -254,12 +260,16 @@ public class DisplayUpdateDownloadWindow extends Overlay<DisplayUpdateDownloadWi
                                 if (verifyResults == null || verifyResults.isEmpty() || verifyFailed.isPresent()) {
                                     showErrorMessage(downloadButton, statusLabel, Res.get("displayUpdateDownloadWindow.verify.failed"));
                                 } else {
+                                    // We set a flag to clear tor cache files at re-start. We cannot clear it now as Tor is used and
+                                    // that can cause problems.
+                                    user.getCookie().putAsBoolean(CookieKey.CLEAN_TOR_DIR_AT_RESTART, true);
                                     verifiedSigLabel.getStyleClass().add("success-text");
                                     new Popup().feedback(Res.get("displayUpdateDownloadWindow.success"))
                                             .actionButtonText(Res.get("displayUpdateDownloadWindow.download.openDir"))
                                             .onAction(() -> {
                                                 try {
                                                     Utilities.openFile(new File(Utilities.getDownloadOfHomeDir()));
+                                                    BisqApp.getShutDownHandler().run();
                                                     doClose();
                                                 } catch (IOException e2) {
                                                     log.error(e2.getMessage());