diff --git a/src/messages/Image.cpp b/src/messages/Image.cpp
index da606ef6e74..66a5390e9a9 100644
--- a/src/messages/Image.cpp
+++ b/src/messages/Image.cpp
@@ -24,6 +24,7 @@
 #include <functional>
 #include <queue>
 #include <thread>
+#include <utility>
 
 // Duration between each check of every Image instance
 const auto IMAGE_POOL_CLEANUP_INTERVAL = std::chrono::minutes(1);
@@ -423,7 +424,7 @@ bool Image::loaded() const
     return this->frames_->current().has_value();
 }
 
-std::optional<QPixmap> Image::pixmapOrLoad() const
+std::optional<QPixmap> Image::pixmapOrLoad(std::function<void()> cb)
 {
     assertInGuiThread();
 
@@ -432,6 +433,10 @@ std::optional<QPixmap> Image::pixmapOrLoad() const
     // See src/messages/layouts/MessageLayoutElement.cpp ImageLayoutElement::paint, for example.
     this->lastUsed_ = std::chrono::steady_clock::now();
 
+    if (cb != nullptr)
+    {
+        this->finishedLoadingCb_ = std::move(cb);
+    }
     this->load();
 
     return this->frames_->current();
@@ -574,6 +579,20 @@ void Image::actuallyLoad()
 
             return true;
         })
+        .finally([weak]() {
+            postToThread([weak]() {
+                auto shared = weak.lock();
+                if (!shared)
+                {
+                    return;
+                }
+
+                if (shared->finishedLoadingCb_ != nullptr)
+                {
+                    shared->finishedLoadingCb_();
+                }
+            });
+        })
         .execute();
 }
 
diff --git a/src/messages/Image.hpp b/src/messages/Image.hpp
index 6e1052a8a2e..7f82c4fab64 100644
--- a/src/messages/Image.hpp
+++ b/src/messages/Image.hpp
@@ -2,6 +2,7 @@
 
 #include "common/Aliases.hpp"
 #include "common/Common.hpp"
+#include "common/NetworkResult.hpp"
 
 #include <boost/variant.hpp>
 #include <pajlada/signals/signal.hpp>
@@ -13,6 +14,7 @@
 
 #include <atomic>
 #include <chrono>
+#include <functional>
 #include <map>
 #include <memory>
 #include <mutex>
@@ -80,7 +82,7 @@ class Image : public std::enable_shared_from_this<Image>
     const Url &url() const;
     bool loaded() const;
     // either returns the current pixmap, or triggers loading it (lazy loading)
-    std::optional<QPixmap> pixmapOrLoad() const;
+    std::optional<QPixmap> pixmapOrLoad(std::function<void()> cb = nullptr);
     void load() const;
     qreal scale() const;
     bool isEmpty() const;
@@ -111,6 +113,8 @@ class Image : public std::enable_shared_from_this<Image>
     // gui thread only
     std::unique_ptr<detail::Frames> frames_{};
 
+    std::function<void()> finishedLoadingCb_;
+
     friend class ImageExpirationPool;
 };
 
diff --git a/src/widgets/listview/ImagePtrItemDelegate.hpp b/src/widgets/listview/ImagePtrItemDelegate.hpp
index 7b7a5163eb4..aa4b3e6b62d 100644
--- a/src/widgets/listview/ImagePtrItemDelegate.hpp
+++ b/src/widgets/listview/ImagePtrItemDelegate.hpp
@@ -1,19 +1,26 @@
 #pragma once
 
+#include "common/QLogging.hpp"
 #include "messages/Image.hpp"
 #include "messages/ImageSet.hpp"
 
 #include <QModelIndex>
-#include <qnamespace.h>
 #include <QPainter>
 #include <QStyledItemDelegate>
+#include <Qt>
+#include <QTableView>
 
 namespace chatterino {
 class ImagePtrItemDelegate : public QStyledItemDelegate
 {
     std::map<QString, ImagePtr> ownedImages_;
+    QTableView *view_;
 
 public:
+    ImagePtrItemDelegate(QTableView *view)
+        : view_(view)
+    {
+    }
     static constexpr auto IMAGE_URL_ROLE = Qt::UserRole + 1;
 
     void paint(QPainter *painter, const QStyleOptionViewItem &option,
@@ -27,6 +34,14 @@ class ImagePtrItemDelegate : public QStyledItemDelegate
             auto opt = img->pixmapOrLoad();
             if (!opt)  // wait for next time
             {
+                if (img->isEmpty())
+                {
+                    painter->drawText(option.rect, "[Error]");
+                }
+                else
+                {
+                    painter->drawText(option.rect, "Loading");
+                }
                 return;
             }
             auto pixmap = *opt;
@@ -56,7 +71,14 @@ class ImagePtrItemDelegate : public QStyledItemDelegate
         }
         auto img = Image::fromUrl(Url{url});
 
-        img->pixmapOrLoad();
+        img->pixmapOrLoad([this, index]() {
+            // wait for it to parse
+            QTimer::singleShot(100, [this, index]() {
+                this->view_->repaint();
+                this->view_->update(index);
+            });
+        });
+
         // You cannot stop me, clang-tidy
         auto *bleh = const_cast<ImagePtrItemDelegate *>(this);
         bleh->ownedImages_[url] = img;
diff --git a/src/widgets/settingspages/ImageUploaderPage.cpp b/src/widgets/settingspages/ImageUploaderPage.cpp
index d75d53f5bf9..c3226aa4e1f 100644
--- a/src/widgets/settingspages/ImageUploaderPage.cpp
+++ b/src/widgets/settingspages/ImageUploaderPage.cpp
@@ -21,7 +21,6 @@
 namespace chatterino {
 
 ImageUploaderPage::ImageUploaderPage()
-    : imgDelegate_(new ImagePtrItemDelegate())
 {
     LayoutCreator<ImageUploaderPage> layoutCreator(this);
     auto tabs = layoutCreator.emplace<QTabWidget>();
@@ -42,6 +41,7 @@ ImageUploaderPage::ImageUploaderPage()
 
         auto *view = layout.emplace<QTableView>().getElement();
         view->setModel(model);
+        this->imgDelegate_ = new ImagePtrItemDelegate(view);
 
         view->setItemDelegateForColumn(0, this->imgDelegate_);
         view->setSelectionMode(QAbstractItemView::SingleSelection);