diff --git a/share/translations/keepassxc_en.ts b/share/translations/keepassxc_en.ts
index 718015913..62b76b4be 100644
--- a/share/translations/keepassxc_en.ts
+++ b/share/translations/keepassxc_en.ts
@@ -6979,6 +6979,14 @@ Do you want to overwrite it?</source>
         <source>Characters: %1</source>
         <translation type="unfinished"></translation>
     </message>
+    <message>
+        <source>Confirm Discard</source>
+        <translation type="unfinished"></translation>
+    </message>
+    <message>
+        <source>Do you want to discard this password?</source>
+        <translation type="unfinished"></translation>
+    </message>
     <message>
         <source>Excluded characters: &quot;0&quot;, &quot;1&quot;, &quot;l&quot;, &quot;I&quot;, &quot;O&quot;, &quot;|&quot;, &quot;﹒&quot;, &quot;B&quot;, &quot;8&quot;, &quot;G&quot;, &quot;6&quot;</source>
         <translation type="unfinished"></translation>
diff --git a/src/gui/DatabaseWidget.cpp b/src/gui/DatabaseWidget.cpp
index 8ec29b951..b3ad68acd 100644
--- a/src/gui/DatabaseWidget.cpp
+++ b/src/gui/DatabaseWidget.cpp
@@ -1973,7 +1973,11 @@ bool DatabaseWidget::lock()
         auto parent = modalWidget->parentWidget();
         while (parent) {
             if (parent == this) {
+                // Preempt any popup questions
+                // TODO: Figure out a way to "reject" or "accept" instead of specific buttons
+                MessageBox::setNextAnswer(MessageBox::Discard);
                 modalWidget->close();
+                MessageBox::setNextAnswer(MessageBox::NoButton);
                 break;
             }
             parent = parent->parentWidget();
diff --git a/src/gui/PasswordGeneratorWidget.cpp b/src/gui/PasswordGeneratorWidget.cpp
index c1e82974e..9aee09ee9 100644
--- a/src/gui/PasswordGeneratorWidget.cpp
+++ b/src/gui/PasswordGeneratorWidget.cpp
@@ -67,7 +67,7 @@ PasswordGeneratorWidget::PasswordGeneratorWidget(QWidget* parent)
     connect(m_ui->buttonGenerate, SIGNAL(clicked()), SLOT(regeneratePassword()));
     connect(m_ui->buttonDeleteWordList, SIGNAL(clicked()), SLOT(deleteWordList()));
     connect(m_ui->buttonAddWordList, SIGNAL(clicked()), SLOT(addWordList()));
-    connect(m_ui->buttonClose, SIGNAL(clicked()), SIGNAL(closed()));
+    connect(m_ui->buttonClose, SIGNAL(clicked()), SLOT(confirmClose()));
 
     connect(m_ui->sliderLength, SIGNAL(valueChanged(int)), SLOT(passwordLengthChanged(int)));
     connect(m_ui->spinBoxLength, SIGNAL(valueChanged(int)), SLOT(passwordLengthChanged(int)));
@@ -121,9 +121,25 @@ PasswordGeneratorWidget::~PasswordGeneratorWidget() = default;
 
 void PasswordGeneratorWidget::closeEvent(QCloseEvent* event)
 {
-    // Emits closed signal when clicking X from title bar
+    confirmClose();
+    event->ignore();
+}
+
+void PasswordGeneratorWidget::confirmClose()
+{
+    // Only ask for discard confirmation if in popup mode
+    if (!m_standalone) {
+        auto result = MessageBox::question(this,
+                                           tr("Confirm Discard"),
+                                           tr("Do you want to discard this password?"),
+                                           MessageBox::Discard | MessageBox::Cancel,
+                                           MessageBox::Cancel);
+        if (result == MessageBox::Cancel) {
+            return;
+        }
+    }
+
     emit closed();
-    QWidget::closeEvent(event);
 }
 
 PasswordGeneratorWidget* PasswordGeneratorWidget::popupGenerator(QWidget* parent)
@@ -325,10 +341,12 @@ void PasswordGeneratorWidget::updatePasswordLengthLabel(const QString& password)
 
 void PasswordGeneratorWidget::applyPassword()
 {
-    saveSettings();
-    m_passwordGenerated = true;
-    emit appliedPassword(m_ui->editNewPassword->text());
-    emit closed();
+    if (!m_standalone) {
+        saveSettings();
+        m_passwordGenerated = true;
+        emit appliedPassword(m_ui->editNewPassword->text());
+        emit closed();
+    }
 }
 
 void PasswordGeneratorWidget::copyPassword()
diff --git a/src/gui/PasswordGeneratorWidget.h b/src/gui/PasswordGeneratorWidget.h
index 2f92a3eca..7a479d4f8 100644
--- a/src/gui/PasswordGeneratorWidget.h
+++ b/src/gui/PasswordGeneratorWidget.h
@@ -69,6 +69,7 @@ public slots:
     void setPasswordVisible(bool visible);
     void deleteWordList();
     void addWordList();
+    void confirmClose();
 
 protected:
     void closeEvent(QCloseEvent* event) override;