diff --git a/src/main/java/org/jabref/gui/DialogService.java b/src/main/java/org/jabref/gui/DialogService.java
index 26cf46c00a1..3be1432d54e 100644
--- a/src/main/java/org/jabref/gui/DialogService.java
+++ b/src/main/java/org/jabref/gui/DialogService.java
@@ -14,6 +14,7 @@
 import javafx.scene.control.ChoiceDialog;
 import javafx.scene.control.DialogPane;
 import javafx.scene.control.TextInputDialog;
+import org.controlsfx.control.textfield.CustomPasswordField;
 
 import org.jabref.gui.util.BaseDialog;
 import org.jabref.gui.util.DirectoryDialogConfiguration;
@@ -161,6 +162,14 @@ boolean showConfirmationDialogWithOptOutAndWait(String title, String content,
                                                     String okButtonLabel, String cancelButtonLabel,
                                                     String optOutMessage, Consumer<Boolean> optOutAction);
 
+    /**
+     * This will create and display new {@link CustomPasswordField} that doesn't show the text, and two buttons
+     * one cancel and one ok.
+     *
+     * @return the entered password if pressed "OK", null otherwise
+     */
+    Optional<String> showPasswordDialogAndWait(String title, String header, String content);
+
     /**
      * Shows a custom dialog without returning any results.
      *
diff --git a/src/main/java/org/jabref/gui/JabRefDialogService.java b/src/main/java/org/jabref/gui/JabRefDialogService.java
index d21e0b3b9d9..9709223cc2b 100644
--- a/src/main/java/org/jabref/gui/JabRefDialogService.java
+++ b/src/main/java/org/jabref/gui/JabRefDialogService.java
@@ -26,6 +26,7 @@
 import javafx.scene.control.DialogPane;
 import javafx.scene.control.Label;
 import javafx.scene.control.TextInputDialog;
+import javafx.scene.layout.HBox;
 import javafx.scene.layout.Pane;
 import javafx.scene.layout.Region;
 import javafx.scene.layout.VBox;
@@ -49,6 +50,7 @@
 import com.tobiasdiez.easybind.EasyBind;
 import org.controlsfx.control.Notifications;
 import org.controlsfx.control.TaskProgressView;
+import org.controlsfx.control.textfield.CustomPasswordField;
 import org.controlsfx.dialog.ExceptionDialog;
 import org.controlsfx.dialog.ProgressDialog;
 import org.slf4j.Logger;
@@ -270,6 +272,30 @@ public <R> Optional<R> showCustomDialogAndWait(javafx.scene.control.Dialog<R> di
         return dialog.showAndWait();
     }
 
+    @Override
+    public Optional<String> showPasswordDialogAndWait(String title, String header, String content) {
+        javafx.scene.control.Dialog<String> dialog = new javafx.scene.control.Dialog<>();
+        dialog.setTitle(title);
+        dialog.setHeaderText(header);
+
+        CustomPasswordField passwordField = new CustomPasswordField();
+
+        HBox box = new HBox();
+        box.setSpacing(10);
+        box.getChildren().addAll(new Label(content), passwordField);
+        dialog.setTitle(title);
+        dialog.getDialogPane().setContent(box);
+
+        dialog.getDialogPane().getButtonTypes().addAll(ButtonType.CANCEL, ButtonType.OK);
+        dialog.setResultConverter(dialogButton -> {
+            if (dialogButton == ButtonType.OK) {
+                return passwordField.getText();
+            }
+            return null;
+        });
+        return dialog.showAndWait();
+    }
+
     @Override
     public <V> void showProgressDialog(String title, String content, Task<V> task) {
         ProgressDialog progressDialog = new ProgressDialog(task);
diff --git a/src/main/java/org/jabref/gui/JabRefGUI.java b/src/main/java/org/jabref/gui/JabRefGUI.java
index 4f5963945ea..5dda14310aa 100644
--- a/src/main/java/org/jabref/gui/JabRefGUI.java
+++ b/src/main/java/org/jabref/gui/JabRefGUI.java
@@ -6,6 +6,7 @@
 import java.util.List;
 import java.util.stream.Collectors;
 
+import com.airhacks.afterburner.injection.Injector;
 import javafx.application.Platform;
 import javafx.scene.Scene;
 import javafx.scene.input.KeyEvent;
@@ -20,6 +21,7 @@
 import org.jabref.gui.shared.SharedDatabaseUIManager;
 import org.jabref.logic.importer.ParserResult;
 import org.jabref.logic.l10n.Localization;
+import org.jabref.logic.net.ProxyRegisterer;
 import org.jabref.logic.shared.DatabaseNotSupportedException;
 import org.jabref.logic.shared.exception.InvalidDBMSConnectionPropertiesException;
 import org.jabref.logic.shared.exception.NotASharedDatabaseException;
@@ -61,6 +63,15 @@ public JabRefGUI(Stage mainStage, List<ParserResult> databases, boolean isBlank,
                 Globals.TASK_EXECUTOR,
                 preferencesService.getInternalPreferences())
                 .checkForNewVersionDelayed();
+
+        if (preferencesService.getProxyPreferences().shouldUseProxy() && preferencesService.getProxyPreferences().shouldUseAuthentication()){
+            DialogService dialogService = Injector.instantiateModelOrService(DialogService.class);
+            dialogService.showPasswordDialogAndWait("Proxy configuration", "Proxy requires password","Password")
+                .ifPresent(newPassword -> {
+                    preferencesService.getProxyPreferences().setPassword(newPassword);
+                    ProxyRegisterer.register(preferencesService.getProxyPreferences());
+                });
+        }
     }
 
     private void openWindow(Stage mainStage) {
diff --git a/src/main/java/org/jabref/preferences/JabRefPreferences.java b/src/main/java/org/jabref/preferences/JabRefPreferences.java
index 3ea8f83a45b..c5104e3ad41 100644
--- a/src/main/java/org/jabref/preferences/JabRefPreferences.java
+++ b/src/main/java/org/jabref/preferences/JabRefPreferences.java
@@ -1552,14 +1552,13 @@ public ProxyPreferences getProxyPreferences() {
                 get(PROXY_PORT),
                 getBoolean(PROXY_USE_AUTHENTICATION),
                 get(PROXY_USERNAME),
-                get(PROXY_PASSWORD));
+                (String) defaults.get(PROXY_PASSWORD));
 
         EasyBind.listen(proxyPreferences.useProxyProperty(), (obs, oldValue, newValue) -> putBoolean(PROXY_USE, newValue));
         EasyBind.listen(proxyPreferences.hostnameProperty(), (obs, oldValue, newValue) -> put(PROXY_HOSTNAME, newValue));
         EasyBind.listen(proxyPreferences.portProperty(), (obs, oldValue, newValue) -> put(PROXY_PORT, newValue));
         EasyBind.listen(proxyPreferences.useAuthenticationProperty(), (obs, oldValue, newValue) -> putBoolean(PROXY_USE_AUTHENTICATION, newValue));
         EasyBind.listen(proxyPreferences.usernameProperty(), (obs, oldValue, newValue) -> put(PROXY_USERNAME, newValue));
-        EasyBind.listen(proxyPreferences.passwordProperty(), (obs, oldValue, newValue) -> put(PROXY_PASSWORD, newValue));
 
         return proxyPreferences;
     }