diff --git a/src/gui/EditWidget.cpp b/src/gui/EditWidget.cpp
index ce80c03b..a58cc6d8 100644
--- a/src/gui/EditWidget.cpp
+++ b/src/gui/EditWidget.cpp
@@ -125,8 +125,14 @@ void EditWidget::enableApplyButton(bool enabled)
 
 void EditWidget::showMessage(const QString& text, MessageWidget::MessageType type)
 {
-    m_ui->messageWidget->setCloseButtonVisible(false);
-    m_ui->messageWidget->showMessage(text, type, 2000);
+    // Show error messages for a longer time to make sure the user can read them
+    if (type == MessageWidget::Error) {
+        m_ui->messageWidget->setCloseButtonVisible(true);
+        m_ui->messageWidget->showMessage(text, type, 15000);
+    } else {
+        m_ui->messageWidget->setCloseButtonVisible(false);
+        m_ui->messageWidget->showMessage(text, type, 2000);
+    }
 }
 
 void EditWidget::hideMessage()
diff --git a/src/gui/EditWidgetIcons.cpp b/src/gui/EditWidgetIcons.cpp
index 2228501b..d5d97dde 100644
--- a/src/gui/EditWidgetIcons.cpp
+++ b/src/gui/EditWidgetIcons.cpp
@@ -92,6 +92,7 @@ EditWidgetIcons::EditWidgetIcons(QWidget* parent)
             SIGNAL(widgetUpdated()));
 
     m_ui->faviconButton->setVisible(false);
+    m_ui->addButton->setEnabled(true);
 }
 
 EditWidgetIcons::~EditWidgetIcons()
@@ -268,7 +269,9 @@ void EditWidgetIcons::fetchFinished()
     }
 
     if (!image.isNull()) {
-        addCustomIcon(image);
+        if (!addCustomIcon(image)) {
+            emit messageEditEntry(tr("Custom icon already exists"), MessageWidget::Information);
+        }
     } else if (!m_urlsToTry.empty()) {
         m_redirects = 0;
         startFetchFavicon(m_urlsToTry.takeFirst());
@@ -324,35 +327,66 @@ void EditWidgetIcons::addCustomIconFromFile()
     if (m_database) {
         QString filter = QString("%1 (%2);;%3 (*)").arg(tr("Images"), Tools::imageReaderFilter(), tr("All files"));
 
-        QString filename = QFileDialog::getOpenFileName(this, tr("Select Image"), "", filter);
-        if (!filename.isEmpty()) {
-            auto icon = QImage(filename);
-            if (!icon.isNull()) {
-                addCustomIcon(QImage(filename));
+        auto filenames = QFileDialog::getOpenFileNames(this, tr("Select Image(s)"), "", filter);
+        if (!filenames.empty()) {
+            QStringList errornames;
+            int numexisting = 0;
+            for (const auto& filename : filenames) {
+                if (!filename.isEmpty()) {
+                    auto icon = QImage(filename);
+                    if (icon.isNull()) {
+                        errornames << filename;
+                    } else if (!addCustomIcon(icon)) {
+                        // Icon already exists in database
+                        ++numexisting;
+                    }
+                }
+            }
+
+            int numloaded = filenames.size() - errornames.size() - numexisting;
+            QString msg;
+
+            if (numloaded > 0) {
+                msg = tr("Successfully loaded %1 of %n icon(s)", "", filenames.size()).arg(numloaded);
             } else {
-                emit messageEditEntry(tr("Can't read icon"), MessageWidget::Error);
+                msg = tr("No icons were loaded");
+            }
+
+            if (numexisting > 0) {
+                msg += "\n" + tr("%n icon(s) already exist in the database", "", numexisting);
+            }
+
+            if (!errornames.empty()) {
+                // Show the first 8 icons that failed to load
+                errornames = errornames.mid(0, 8);
+                emit messageEditEntry(msg + "\n" + tr("The following icon(s) failed:", "", errornames.size()) +
+                                      "\n" + errornames.join("\n"), MessageWidget::Error);
+            } else if (numloaded > 0) {
+                emit messageEditEntry(msg, MessageWidget::Positive);
+            } else {
+                emit messageEditEntry(msg, MessageWidget::Information);
             }
         }
     }
 }
 
-void EditWidgetIcons::addCustomIcon(const QImage& icon)
+bool EditWidgetIcons::addCustomIcon(const QImage& icon)
 {
+    bool added = false;
     if (m_database) {
-        Uuid uuid = m_database->metadata()->findCustomIcon(icon);
+        // Don't add an icon larger than 128x128, but retain original size if smaller
+        auto scaledicon = icon;
+        if (icon.width() > 128 || icon.height() > 128) {
+            scaledicon = icon.scaled(128, 128);
+        }
+
+        Uuid uuid = m_database->metadata()->findCustomIcon(scaledicon);
         if (uuid.isNull()) {
             uuid = Uuid::random();
-            // Don't add an icon larger than 128x128, but retain original size if smaller
-            if (icon.width() > 128 || icon.height() > 128) {
-                m_database->metadata()->addCustomIcon(uuid, icon.scaled(128, 128));
-            } else {
-                m_database->metadata()->addCustomIcon(uuid, icon);
-            }
-
+            m_database->metadata()->addCustomIcon(uuid, scaledicon);
             m_customIconModel->setIcons(m_database->metadata()->customIconsScaledPixmaps(),
                                         m_database->metadata()->customIconsOrder());
-        } else {
-            emit messageEditEntry(tr("Custom icon already exists"), MessageWidget::Information);
+            added = true;
         }
 
         // Select the new or existing icon
@@ -362,6 +396,8 @@ void EditWidgetIcons::addCustomIcon(const QImage& icon)
 
         emit widgetUpdated();
     }
+
+    return added;
 }
 
 void EditWidgetIcons::removeCustomIcon()
@@ -458,7 +494,6 @@ void EditWidgetIcons::updateWidgetsDefaultIcons(bool check)
             m_ui->defaultIconsView->setCurrentIndex(index);
         }
         m_ui->customIconsView->selectionModel()->clearSelection();
-        m_ui->addButton->setEnabled(false);
         m_ui->deleteButton->setEnabled(false);
     }
 }
@@ -473,7 +508,6 @@ void EditWidgetIcons::updateWidgetsCustomIcons(bool check)
             m_ui->customIconsView->setCurrentIndex(index);
         }
         m_ui->defaultIconsView->selectionModel()->clearSelection();
-        m_ui->addButton->setEnabled(true);
         m_ui->deleteButton->setEnabled(true);
     }
 }
diff --git a/src/gui/EditWidgetIcons.h b/src/gui/EditWidgetIcons.h
index 94630157..e01ae4b1 100644
--- a/src/gui/EditWidgetIcons.h
+++ b/src/gui/EditWidgetIcons.h
@@ -88,7 +88,7 @@ private slots:
     void fetchReadyRead();
     void fetchCanceled();
     void addCustomIconFromFile();
-    void addCustomIcon(const QImage& icon);
+    bool addCustomIcon(const QImage& icon);
     void removeCustomIcon();
     void updateWidgetsDefaultIcons(bool checked);
     void updateWidgetsCustomIcons(bool checked);