diff --git a/src/Gui/SettingsDialog/GeneralOptionsPage.h b/src/Gui/SettingsDialog/GeneralOptionsPage.h
--- a/src/Gui/SettingsDialog/GeneralOptionsPage.h
+++ b/src/Gui/SettingsDialog/GeneralOptionsPage.h
@@ -23,6 +23,7 @@
 #include "SettingsPage.h"
 
 class QCheckBox;
+class QRadioButton;
 
 class GeneralOptionsPage : public SettingsPage
 {
@@ -43,7 +44,8 @@
 
     private:
 
-    QCheckBox *mRememberRect;
+    QRadioButton* mRememberAlways;
+    QRadioButton* mRememberUntilClosed;
     QCheckBox *mUseLightBackground;
     QCheckBox *mShowMagnifier;
 };
diff --git a/src/Gui/SettingsDialog/GeneralOptionsPage.cpp b/src/Gui/SettingsDialog/GeneralOptionsPage.cpp
--- a/src/Gui/SettingsDialog/GeneralOptionsPage.cpp
+++ b/src/Gui/SettingsDialog/GeneralOptionsPage.cpp
@@ -22,34 +22,50 @@
 #include "SpectacleConfig.h"
 
 #include <KLocalizedString>
+#include <KTitleWidget>
 
+#include <QButtonGroup>
 #include <QCheckBox>
 #include <QFormLayout>
-#include <QGroupBox>
+#include <QRadioButton>
 
 GeneralOptionsPage::GeneralOptionsPage(QWidget *parent) :
     SettingsPage(parent)
 {
     QFormLayout *mainLayout = new QFormLayout(this);
     setLayout(mainLayout);
 
     // Rectangular Region settings
+    KTitleWidget *titleWidget = new KTitleWidget(this);
+    titleWidget->setText(i18n("Rectangular Region:"));
+    titleWidget->setLevel(2);
+    mainLayout->addRow(titleWidget);
 
     // use light background
     mUseLightBackground = new QCheckBox(i18n("Use light background"), this);
     connect(mUseLightBackground, &QCheckBox::toggled, this, &GeneralOptionsPage::markDirty);
-    mainLayout->addRow(i18n("Rectangular Region:"), mUseLightBackground);
-
-    // remember Rectangular Region box
-    mRememberRect = new QCheckBox(i18n("Remember selected area"), this);
-    connect(mRememberRect, &QCheckBox::toggled, this, &GeneralOptionsPage::markDirty);
-    mainLayout->addRow(QString(), mRememberRect);
+    mainLayout->addRow(i18n("General:"), mUseLightBackground);
 
     // show magnifier
     mShowMagnifier = new QCheckBox(i18n("Show magnifier"), this);
     connect(mShowMagnifier, &QCheckBox::toggled, this, &GeneralOptionsPage::markDirty);
     mainLayout->addRow(QString(), mShowMagnifier);
 
+    // remember Rectangular Region box
+    QButtonGroup* rememberGroup = new QButtonGroup(this);
+    rememberGroup->setExclusive(true);
+    QRadioButton* neverButton = new QRadioButton(i18n("Never"), this);
+    mRememberAlways = new QRadioButton(i18n("Always"), this);
+    mRememberUntilClosed = new QRadioButton(i18n("Until Spectacle is closed"), this);
+    rememberGroup->addButton(neverButton);
+    rememberGroup->addButton(mRememberAlways);
+    rememberGroup->addButton(mRememberUntilClosed);
+    neverButton->setChecked(true);
+    connect(rememberGroup, static_cast<void(QButtonGroup::*)(QAbstractButton *, bool)>(&QButtonGroup::buttonToggled), this, &GeneralOptionsPage::markDirty);
+    mainLayout->addRow(i18n("Remember selected area:"), neverButton);
+    mainLayout->addRow(QString(), mRememberAlways);
+    mainLayout->addRow(QString(), mRememberUntilClosed );
+
     // read in the data
     resetChanges();
 }
@@ -64,7 +80,8 @@
     SpectacleConfig *cfgManager = SpectacleConfig::instance();
 
     cfgManager->setUseLightRegionMaskColour(mUseLightBackground->checkState() == Qt::Checked);
-    cfgManager->setRememberLastRectangularRegion(mRememberRect->checkState() == Qt::Checked);
+    cfgManager->setRememberLastRectangularRegion(mRememberUntilClosed->isChecked() || mRememberAlways->isChecked());
+    cfgManager->setAlwaysRememberRegion (mRememberAlways->isChecked());
     cfgManager->setShowMagnifierChecked(mShowMagnifier->checkState() == Qt::Checked);
 
     mChangesMade = false;
@@ -75,7 +92,8 @@
     SpectacleConfig *cfgManager = SpectacleConfig::instance();
 
     mUseLightBackground->setChecked(cfgManager->useLightRegionMaskColour());
-    mRememberRect->setChecked(cfgManager->rememberLastRectangularRegion());
+    mRememberUntilClosed->setChecked(cfgManager->rememberLastRectangularRegion());
+    mRememberAlways->setChecked(cfgManager->alwaysRememberRegion());
     mShowMagnifier->setChecked(cfgManager->showMagnifierChecked());
 
     mChangesMade = false;
diff --git a/src/SpectacleConfig.h b/src/SpectacleConfig.h
--- a/src/SpectacleConfig.h
+++ b/src/SpectacleConfig.h
@@ -96,6 +96,9 @@
     bool rememberLastRectangularRegion() const;
     void setRememberLastRectangularRegion(bool enabled);
 
+    bool alwaysRememberRegion() const;
+    void setAlwaysRememberRegion(bool enabled);
+
     bool useLightRegionMaskColour() const;
     void setUseLightRegionMaskColour(bool enabled);
 
diff --git a/src/SpectacleConfig.cpp b/src/SpectacleConfig.cpp
--- a/src/SpectacleConfig.cpp
+++ b/src/SpectacleConfig.cpp
@@ -215,6 +215,18 @@
     mGuiConfig.sync();
 }
 
+bool SpectacleConfig::alwaysRememberRegion() const
+{
+    // Default Value is for compatibility reasons as the old behavior was always to remember across restarts
+    return mGuiConfig.readEntry(QStringLiteral("alwaysRememberRegion"), rememberLastRectangularRegion());
+}
+
+void SpectacleConfig::setAlwaysRememberRegion (bool enabled)
+{
+    mGuiConfig.writeEntry(QStringLiteral("alwaysRememberRegion"), enabled);
+    mGuiConfig.sync();
+}
+
 // use light region mask colour
 
 bool SpectacleConfig::useLightRegionMaskColour() const
diff --git a/src/SpectacleCore.cpp b/src/SpectacleCore.cpp
--- a/src/SpectacleCore.cpp
+++ b/src/SpectacleCore.cpp
@@ -84,6 +84,12 @@
         delayMsec = 0;
     }
 
+    //Reset last region if it should not be remembered across restarts
+    SpectacleConfig* cfg = SpectacleConfig::instance();
+    if(!cfg->alwaysRememberRegion()) {
+        cfg->setCropRegion(QRect());
+    }
+
     connect(mExportManager, &ExportManager::errorMessage, this, &SpectacleCore::showErrorMessage);
     connect(this, &SpectacleCore::errorMessage, this, &SpectacleCore::showErrorMessage);
     connect(mImageGrabber, &ImageGrabber::pixmapChanged, this, &SpectacleCore::screenshotUpdated);