diff --git a/share/translations/keepassxc_en.ts b/share/translations/keepassxc_en.ts
index 16cd879b9..113053acb 100644
--- a/share/translations/keepassxc_en.ts
+++ b/share/translations/keepassxc_en.ts
@@ -573,6 +573,10 @@
         <source>Font size selection</source>
         <translation type="unfinished"></translation>
     </message>
+    <message>
+        <source>Skip confirmation for main window Auto-Type actions</source>
+        <translation type="unfinished"></translation>
+    </message>
 </context>
 <context>
     <name>ApplicationSettingsWidgetSecurity</name>
diff --git a/src/core/Config.cpp b/src/core/Config.cpp
index f1a78830d..04b724fb1 100644
--- a/src/core/Config.cpp
+++ b/src/core/Config.cpp
@@ -147,6 +147,7 @@ static const QHash<Config::ConfigKey, ConfigDirective> configStrings = {
     {Config::Security_HidePasswordPreviewPanel, {QS("Security/HidePasswordPreviewPanel"), Roaming, true}},
     {Config::Security_HideTotpPreviewPanel, {QS("Security/HideTotpPreviewPanel"), Roaming, false}},
     {Config::Security_AutoTypeAsk, {QS("Security/AutotypeAsk"), Roaming, true}},
+    {Config::Security_AutoTypeSkipMainWindowConfirmation, {QS("Security/AutoTypeSkipMainWindowConfirmation"), Roaming, false}},
     {Config::Security_IconDownloadFallback, {QS("Security/IconDownloadFallback"), Roaming, false}},
     {Config::Security_NoConfirmMoveEntryToRecycleBin,{QS("Security/NoConfirmMoveEntryToRecycleBin"), Roaming, true}},
     {Config::Security_EnableCopyOnDoubleClick,{QS("Security/EnableCopyOnDoubleClick"), Roaming, false}},
diff --git a/src/core/Config.h b/src/core/Config.h
index 5678bbc6e..9385f9ef1 100644
--- a/src/core/Config.h
+++ b/src/core/Config.h
@@ -129,6 +129,7 @@ public:
         Security_HidePasswordPreviewPanel,
         Security_HideTotpPreviewPanel,
         Security_AutoTypeAsk,
+        Security_AutoTypeSkipMainWindowConfirmation,
         Security_IconDownloadFallback,
         Security_NoConfirmMoveEntryToRecycleBin,
         Security_EnableCopyOnDoubleClick,
diff --git a/src/gui/ApplicationSettingsWidget.cpp b/src/gui/ApplicationSettingsWidget.cpp
index 8d53d6f0f..2fd0b6d7a 100644
--- a/src/gui/ApplicationSettingsWidget.cpp
+++ b/src/gui/ApplicationSettingsWidget.cpp
@@ -129,6 +129,8 @@ ApplicationSettingsWidget::ApplicationSettingsWidget(QWidget* parent)
     connect(m_generalUi->backupFilePathPicker, SIGNAL(pressed()), SLOT(selectBackupDirectory()));
     connect(m_generalUi->showExpiredEntriesOnDatabaseUnlockCheckBox, SIGNAL(toggled(bool)),
             SLOT(showExpiredEntriesOnDatabaseUnlockToggled(bool)));
+    connect(m_generalUi->autoTypeAskCheckBox, SIGNAL(toggled(bool)),
+            SLOT(autoTypeAskToggled(bool)));
 
     connect(m_secUi->clearClipboardCheckBox, SIGNAL(toggled(bool)),
             m_secUi->clearClipboardSpinBox, SLOT(setEnabled(bool)));
@@ -302,6 +304,9 @@ void ApplicationSettingsWidget::loadSettings()
     showExpiredEntriesOnDatabaseUnlockToggled(m_generalUi->showExpiredEntriesOnDatabaseUnlockCheckBox->isChecked());
 
     m_generalUi->autoTypeAskCheckBox->setChecked(config()->get(Config::Security_AutoTypeAsk).toBool());
+    m_generalUi->autoTypeSkipMainWindowConfirmationCheckBox->setChecked(
+        config()->get(Config::Security_AutoTypeSkipMainWindowConfirmation).toBool());
+    autoTypeAskToggled(m_generalUi->autoTypeAskCheckBox->isChecked());
     m_generalUi->autoTypeRelockDatabaseCheckBox->setChecked(config()->get(Config::Security_RelockAutoType).toBool());
 
     if (autoType()->isAvailable()) {
@@ -445,6 +450,8 @@ void ApplicationSettingsWidget::saveSettings()
                   m_generalUi->showExpiredEntriesOnDatabaseUnlockOffsetSpinBox->value());
 
     config()->set(Config::Security_AutoTypeAsk, m_generalUi->autoTypeAskCheckBox->isChecked());
+    config()->set(Config::Security_AutoTypeSkipMainWindowConfirmation,
+                  m_generalUi->autoTypeSkipMainWindowConfirmationCheckBox->isChecked());
     config()->set(Config::Security_RelockAutoType, m_generalUi->autoTypeRelockDatabaseCheckBox->isChecked());
 
     if (autoType()->isAvailable()) {
@@ -618,6 +625,11 @@ void ApplicationSettingsWidget::showExpiredEntriesOnDatabaseUnlockToggled(bool c
     m_generalUi->showExpiredEntriesOnDatabaseUnlockOffsetSpinBox->setEnabled(checked);
 }
 
+void ApplicationSettingsWidget::autoTypeAskToggled(bool checked)
+{
+    m_generalUi->autoTypeSkipMainWindowConfirmationCheckBox->setEnabled(checked);
+}
+
 void ApplicationSettingsWidget::selectBackupDirectory()
 {
     auto backupDirectory =
diff --git a/src/gui/ApplicationSettingsWidget.h b/src/gui/ApplicationSettingsWidget.h
index 7e43196b1..25450600c 100644
--- a/src/gui/ApplicationSettingsWidget.h
+++ b/src/gui/ApplicationSettingsWidget.h
@@ -63,6 +63,7 @@ private slots:
     void rememberDatabasesToggled(bool checked);
     void checkUpdatesToggled(bool checked);
     void showExpiredEntriesOnDatabaseUnlockToggled(bool checked);
+    void autoTypeAskToggled(bool checked);
     void selectBackupDirectory();
 
 private:
diff --git a/src/gui/ApplicationSettingsWidgetGeneral.ui b/src/gui/ApplicationSettingsWidgetGeneral.ui
index eb69f2615..71ea8c47f 100644
--- a/src/gui/ApplicationSettingsWidgetGeneral.ui
+++ b/src/gui/ApplicationSettingsWidgetGeneral.ui
@@ -1157,6 +1157,42 @@
          </property>
         </widget>
        </item>
+       <item>
+        <layout class="QHBoxLayout" name="autoTypeSkipMainWindowLayout">
+         <property name="spacing">
+          <number>0</number>
+         </property>
+         <item>
+          <spacer name="autoTypeSkipMainWindowSpacer">
+           <property name="orientation">
+            <enum>Qt::Horizontal</enum>
+           </property>
+           <property name="sizeType">
+            <enum>QSizePolicy::Fixed</enum>
+           </property>
+           <property name="sizeHint" stdset="0">
+            <size>
+             <width>30</width>
+             <height>20</height>
+            </size>
+           </property>
+          </spacer>
+         </item>
+         <item>
+          <widget class="QCheckBox" name="autoTypeSkipMainWindowConfirmationCheckBox">
+           <property name="enabled">
+            <bool>false</bool>
+           </property>
+           <property name="text">
+            <string>Skip confirmation for main window Auto-Type actions</string>
+           </property>
+           <property name="checked">
+            <bool>false</bool>
+           </property>
+          </widget>
+         </item>
+        </layout>
+       </item>
        <item>
         <widget class="QCheckBox" name="autoTypeHideExpiredEntryCheckBox">
          <property name="text">
diff --git a/src/gui/DatabaseWidget.cpp b/src/gui/DatabaseWidget.cpp
index a9f7f5a81..e84916960 100644
--- a/src/gui/DatabaseWidget.cpp
+++ b/src/gui/DatabaseWidget.cpp
@@ -877,12 +877,18 @@ void DatabaseWidget::performAutoType(const QString& sequence)
 {
     auto currentEntry = currentSelectedEntry();
     if (currentEntry) {
-        // TODO: Include name of previously active window in confirmation question
-        if (config()->get(Config::Security_AutoTypeAsk).toBool()
-            && MessageBox::question(
-                   this, tr("Confirm Auto-Type"), tr("Perform Auto-Type into the previously active window?"))
-                   != MessageBox::Yes) {
-            return;
+        // Check if we need to ask for confirmation
+        bool shouldAsk = config()->get(Config::Security_AutoTypeAsk).toBool();
+        bool skipMainWindowConfirmation = config()->get(Config::Security_AutoTypeSkipMainWindowConfirmation).toBool();
+
+        // Show confirmation if Security_AutoTypeAsk is true AND Security_AutoTypeSkipMainWindowConfirmation is false
+        if (shouldAsk && !skipMainWindowConfirmation) {
+            // TODO: Include name of previously active window in confirmation question
+            if (MessageBox::question(
+                    this, tr("Confirm Auto-Type"), tr("Perform Auto-Type into the previously active window?"))
+                != MessageBox::Yes) {
+                return;
+            }
         }
 
         if (sequence.isEmpty()) {