diff --git a/src/ui/mainwindow.cpp b/src/ui/mainwindow.cpp
index 89b130f5b..1dd136108 100644
--- a/src/ui/mainwindow.cpp
+++ b/src/ui/mainwindow.cpp
@@ -712,6 +712,9 @@ MainWindow::MainWindow(
 
   ReloadSettings();
 
+  // Reload pretty OSD to avoid issues with fonts
+  osd_->ReloadPrettyOSDSettings();
+
 #ifndef Q_OS_DARWIN
   StartupBehaviour behaviour =
       StartupBehaviour(settings_.value("startupbehaviour", Startup_Remember).toInt());
diff --git a/src/ui/settingsdialog.cpp b/src/ui/settingsdialog.cpp
index fc7a6a81e..b47319bb0 100644
--- a/src/ui/settingsdialog.cpp
+++ b/src/ui/settingsdialog.cpp
@@ -284,6 +284,7 @@ SettingsDialog::SettingsDialog(BackgroundStreams* streams, QWidget* parent)
   connect(ui_->notifications_opacity, SIGNAL(valueChanged(int)), SLOT(PrettyOpacityChanged(int)));
   connect(ui_->notifications_bg_preset, SIGNAL(activated(int)), SLOT(PrettyColorPresetChanged(int)));
   connect(ui_->notifications_fg_choose, SIGNAL(clicked()), SLOT(ChooseFgColor()));
+  connect(ui_->notifications_font_choose, SIGNAL(clicked()), SLOT(ChooseFont()));
   connect(ui_->notifications_exp_chooser1, SIGNAL(triggered(QAction*)), SLOT(InsertVariableFirstLine(QAction*)));
   connect(ui_->notifications_exp_chooser2, SIGNAL(triggered(QAction*)), SLOT(InsertVariableSecondLine(QAction*)));
 
@@ -434,6 +435,7 @@ void SettingsDialog::accept() {
   s.setValue("background_opacity", pretty_popup_->background_opacity());
   s.setValue("popup_display", pretty_popup_->popup_display());
   s.setValue("popup_pos", pretty_popup_->popup_pos());
+  s.setValue("font", pretty_popup_->font().toString());
   s.endGroup();
 
   // Network proxy
@@ -739,6 +741,13 @@ void SettingsDialog::ChooseFgColor() {
   pretty_popup_->set_foreground_color(color.rgb());
 }
 
+void SettingsDialog::ChooseFont() {
+  bool ok;
+  QFont font = QFontDialog::getFont(&ok, pretty_popup_->font(), this);
+  if (ok)
+    pretty_popup_->set_font(font);
+}
+
 void SettingsDialog::ShowTrayIconToggled(bool on) {
   ui_->b_always_hide_->setEnabled(on);
   if (!on && ui_->b_always_hide_->isChecked())
diff --git a/src/ui/settingsdialog.h b/src/ui/settingsdialog.h
index b4ea6e042..509e90982 100644
--- a/src/ui/settingsdialog.h
+++ b/src/ui/settingsdialog.h
@@ -115,6 +115,7 @@ class SettingsDialog : public QDialog {
   void PrettyColorPresetChanged(int index);
   void ChooseBgColor();
   void ChooseFgColor();
+  void ChooseFont();
 
   void UpdatePopupVisible();
   void ShowTrayIconToggled(bool on);
diff --git a/src/ui/settingsdialog.ui b/src/ui/settingsdialog.ui
index 86cf19d96..d75f99aaa 100644
--- a/src/ui/settingsdialog.ui
+++ b/src/ui/settingsdialog.ui
@@ -6,8 +6,8 @@
    <rect>
     <x>0</x>
     <y>0</y>
-    <width>746</width>
-    <height>642</height>
+    <width>744</width>
+    <height>640</height>
    </rect>
   </property>
   <property name="windowTitle">
@@ -975,7 +975,7 @@
            <property name="title">
             <string>Pretty OSD options</string>
            </property>
-           <layout class="QFormLayout" name="formLayout_2">
+           <layout class="QGridLayout" name="gridLayout_2">
             <item row="0" column="0">
              <widget class="QLabel" name="label_4">
               <property name="text">
@@ -983,7 +983,7 @@
               </property>
              </widget>
             </item>
-            <item row="0" column="1">
+            <item row="0" column="1" colspan="2">
              <widget class="QSlider" name="notifications_opacity">
               <property name="orientation">
                <enum>Qt::Horizontal</enum>
@@ -1019,7 +1019,7 @@
             <item row="2" column="0">
              <widget class="QLabel" name="label_6">
               <property name="text">
-               <string>Text color</string>
+               <string>Text options</string>
               </property>
              </widget>
             </item>
@@ -1030,6 +1030,13 @@
               </property>
              </widget>
             </item>
+            <item row="2" column="2">
+             <widget class="QPushButton" name="notifications_font_choose">
+              <property name="text">
+               <string>Choose font...</string>
+              </property>
+             </widget>
+            </item>
            </layout>
           </widget>
          </item>
diff --git a/src/widgets/osd.cpp b/src/widgets/osd.cpp
index 7e640560c..89618b42a 100644
--- a/src/widgets/osd.cpp
+++ b/src/widgets/osd.cpp
@@ -84,13 +84,21 @@ void OSD::ReloadSettings() {
   if (!SupportsTrayPopups() && behaviour_ == TrayPopup)
     behaviour_ = Disabled;
 
+  ReloadPrettyOSDSettings();
+}
+
+// Reload just Pretty OSD settings, not everything
+void OSD::ReloadPrettyOSDSettings() {
   pretty_popup_->set_popup_duration(timeout_msec_);
   pretty_popup_->ReloadSettings();
 }
 
 void OSD::SongChanged(const Song &song) {
-  // no cover art yet
-  tray_icon_->SetNowPlaying(song, NULL);
+  // Don't change tray icon details if it's a preview
+  if (!preview_mode_) {
+    // no cover art yet
+    tray_icon_->SetNowPlaying(song, NULL);
+  }
 
   QStringList message_parts;
   QString summary;
@@ -145,7 +153,9 @@ void OSD::SongChanged(const Song &song) {
 }
 
 void OSD::CoverArtPathReady(const Song& song, const QString& image_path) {
-  tray_icon_->SetNowPlaying(song, image_path);
+  // Don't change tray icon details if it's a preview
+  if (!preview_mode_)
+    tray_icon_->SetNowPlaying(song, image_path);
 }
 
 void OSD::AlbumArtLoaded(quint64 id, const QImage& image) {
@@ -354,8 +364,8 @@ void OSD::ShowPreview(const Behaviour type, const QString& line1, const QString&
   custom_text2_ = line2;
   if (!use_custom_text_)
     use_custom_text_ = true;
-  SongChanged(song);
 
   // We want to reload the settings, but we can't do this here because the cover art loading is asynch
   preview_mode_ = true;
+  SongChanged(song);
 }
diff --git a/src/widgets/osd.h b/src/widgets/osd.h
index 05d12d1ce..cb6577068 100644
--- a/src/widgets/osd.h
+++ b/src/widgets/osd.h
@@ -63,6 +63,8 @@ class OSD : public QObject {
   static bool SupportsNativeNotifications();
   static bool SupportsTrayPopups();
 
+  void ReloadPrettyOSDSettings();
+
  public slots:
   void ReloadSettings();
 
diff --git a/src/widgets/osdpretty.cpp b/src/widgets/osdpretty.cpp
index f130dde0f..99ee3a9de 100644
--- a/src/widgets/osdpretty.cpp
+++ b/src/widgets/osdpretty.cpp
@@ -59,6 +59,7 @@ OSDPretty::OSDPretty(Mode mode, QWidget *parent)
     background_color_(kPresetBlue),
     background_opacity_(0.85),
     popup_display_(0),
+    font_(QFont()),
     timeout_(new QTimer(this)),
     fading_enabled_(false),
     fader_(new QTimeLine(300, this))
@@ -115,7 +116,7 @@ OSDPretty::OSDPretty(Mode mode, QWidget *parent)
   int margin = l->margin() + kDropShadowSize;
   l->setMargin(margin);
 
-  Load();
+  // Don't load settings here, they will be reloaded anyway on creation
 }
 
 OSDPretty::~OSDPretty() {
@@ -138,7 +139,9 @@ void OSDPretty::Load() {
   background_opacity_ = s.value("background_opacity", 0.85).toDouble();
   popup_display_ = s.value("popup_display", -1).toInt();
   popup_pos_ = s.value("popup_pos", QPoint(0, 0)).toPoint();
+  font_.fromString(s.value("font", "Verdana,9,-1,5,50,0,0,0,0,0").toString());
 
+  set_font(font());
   set_foreground_color(foreground_color());
 }
 
@@ -243,8 +246,11 @@ void OSDPretty::showEvent(QShowEvent* e) {
     fader_->setDirection(QTimeLine::Forward);
     fader_->start(); // Timeout will be started in FaderFinished
   }
-  else if (mode_ == Mode_Popup)
+  else if (mode_ == Mode_Popup) {
     timeout_->start();
+    // Ensures it is above when showing the preview
+    raise();
+  }
 }
 
 void OSDPretty::setVisible(bool visible) {
@@ -401,3 +407,16 @@ void OSDPretty::mouseReleaseEvent(QMouseEvent *) {
     popup_pos_ = current_pos();
   }
 }
+
+void OSDPretty::set_font(QFont font) {
+  font_ = font;
+
+  // Update the UI
+  ui_->summary->setFont(font);
+  ui_->message->setFont(font);
+  // Now adjust OSD size so everything fits
+  ui_->verticalLayout->activate();
+  resize(sizeHint());
+  // Update the position after font change
+  Reposition();
+}
diff --git a/src/widgets/osdpretty.h b/src/widgets/osdpretty.h
index fa734b526..afcc1e214 100644
--- a/src/widgets/osdpretty.h
+++ b/src/widgets/osdpretty.h
@@ -63,12 +63,14 @@ class OSDPretty : public QWidget {
   void set_foreground_color(QRgb color);
   void set_background_color(QRgb color);
   void set_background_opacity(qreal opacity);
+  void set_font(QFont font);
 
   QRgb foreground_color() const { return foreground_color_.rgb(); }
   QRgb background_color() const { return background_color_.rgb(); }
   qreal background_opacity() const { return background_opacity_; }
   int popup_display() const { return popup_display_; }
   QPoint popup_pos() const { return popup_pos_; }
+  QFont font() const { return font_; }
 
   // When the user has been moving the popup, use these to get its current
   // position and screen.  Note that these return invalid values if the popup
@@ -112,6 +114,7 @@ class OSDPretty : public QWidget {
   float background_opacity_;
   int popup_display_; // -1 for default
   QPoint popup_pos_;
+  QFont font_;
 
   // Cached pixmaps
   QPixmap shadow_edge_[4];
diff --git a/src/widgets/osdpretty.ui b/src/widgets/osdpretty.ui
index ebea30d76..91fafeb54 100644
--- a/src/widgets/osdpretty.ui
+++ b/src/widgets/osdpretty.ui
@@ -6,8 +6,8 @@
    <rect>
     <x>0</x>
     <y>0</y>
-    <width>410</width>
-    <height>94</height>
+    <width>396</width>
+    <height>80</height>
    </rect>
   </property>
   <property name="styleSheet">
@@ -31,6 +31,12 @@
      </property>
      <item>
       <widget class="QLabel" name="summary">
+       <property name="sizePolicy">
+        <sizepolicy hsizetype="Expanding" vsizetype="Preferred">
+         <horstretch>0</horstretch>
+         <verstretch>0</verstretch>
+        </sizepolicy>
+       </property>
        <property name="minimumSize">
         <size>
          <width>300</width>
@@ -39,7 +45,7 @@
        </property>
        <property name="maximumSize">
         <size>
-         <width>300</width>
+         <width>400</width>
          <height>16777215</height>
         </size>
        </property>
@@ -50,6 +56,12 @@
      </item>
      <item>
       <widget class="QLabel" name="message">
+       <property name="sizePolicy">
+        <sizepolicy hsizetype="Expanding" vsizetype="Preferred">
+         <horstretch>0</horstretch>
+         <verstretch>0</verstretch>
+        </sizepolicy>
+       </property>
        <property name="maximumSize">
         <size>
          <width>400</width>