diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index fe5ddf821..5b256a103 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -446,7 +446,6 @@ set(SOURCE_FILES
         singletons/Fonts.hpp
         singletons/imageuploader/ImageUploader.cpp
         singletons/imageuploader/ImageUploader.hpp
-        singletons/imageuploader/UploadedImage.hpp
         singletons/imageuploader/UploadedImageModel.cpp
         singletons/imageuploader/UploadedImageModel.hpp
         singletons/Logging.cpp
diff --git a/src/singletons/imageuploader/ImageUploader.cpp b/src/singletons/imageuploader/ImageUploader.cpp
index d27f635e9..c179048de 100644
--- a/src/singletons/imageuploader/ImageUploader.cpp
+++ b/src/singletons/imageuploader/ImageUploader.cpp
@@ -13,6 +13,7 @@
 #include "singletons/Settings.hpp"
 #include "util/CombinePath.hpp"
 #include "util/RapidjsonHelpers.hpp"
+#include "util/Result.hpp"
 #include "widgets/helper/ResizingTextEdit.hpp"
 
 #include <QBuffer>
@@ -28,6 +29,7 @@
 #include <rapidjson/document.h>
 
 #include <memory>
+#include <vector>
 
 #include <utility>
 
@@ -50,6 +52,48 @@ std::optional<QByteArray> convertToPng(const QImage &image)
     return std::nullopt;
 }
 
+using namespace chatterino;
+Result<std::vector<UploadedImage>, QString> loadLogFile(
+    const QString &logFileName)
+{
+    //reading existing logs
+    QFile logReadFile(logFileName);
+    bool isLogFileOkay =
+        logReadFile.open(QIODevice::ReadWrite | QIODevice::Text);
+    if (!isLogFileOkay)
+    {
+        return QString("Failed to open log file with links at ") + logFileName;
+    }
+    auto logs = logReadFile.readAll();
+    if (logs.isEmpty())
+    {
+        logs = QJsonDocument(QJsonArray()).toJson();
+    }
+    logReadFile.close();
+    QJsonArray entries = QJsonDocument::fromJson(logs).array();
+    std::vector<UploadedImage> images;
+    for (const auto &entry : entries)
+    {
+        if (!entry.isObject())
+        {
+            qCWarning(chatterinoImageuploader)
+                << "History file contains non-Object JSON data!";
+            continue;
+        }
+        auto obj = entry.toObject();
+        images.emplace_back(obj);
+    }
+    return images;
+}
+
+QString getLogFilePath()
+{
+    return combinePath((getSettings()->logPath.getValue().isEmpty()
+                            ? getIApp()->getPaths().messageLogDirectory
+                            : getSettings()->logPath),
+                       "ImageUploader.json");
+}
+
 }  // namespace
 
 namespace chatterino {
@@ -59,51 +103,36 @@ void ImageUploader::logToFile(const QString &originalFilePath,
                               const QString &imageLink,
                               const QString &deletionLink, ChannelPtr channel)
 {
-    const QString logFileName =
-        combinePath((getSettings()->logPath.getValue().isEmpty()
-                         ? getIApp()->getPaths().messageLogDirectory
-                         : getSettings()->logPath),
-                    "ImageUploader.json");
-
-    //reading existing logs
-    QFile logReadFile(logFileName);
-    bool isLogFileOkay =
-        logReadFile.open(QIODevice::ReadWrite | QIODevice::Text);
-    if (!isLogFileOkay)
+    const QString logFileName = getLogFilePath();
+    auto res = loadLogFile(logFileName);
+    if (!res.isOk())
     {
-        channel->addMessage(makeSystemMessage(
-            QString("Failed to open log file with links at ") + logFileName));
+        channel->addMessage(makeSystemMessage(res.error()));
         return;
     }
-    auto logs = logReadFile.readAll();
-    if (logs.isEmpty())
-    {
-        logs = QJsonDocument(QJsonArray()).toJson();
-    }
-    logReadFile.close();
-
+    auto entries = res.value();
     //writing new data to logs
-    QJsonObject newLogEntry;
-    newLogEntry["channelName"] = channel->getName();
-    newLogEntry["deletionLink"] =
-        deletionLink.isEmpty() ? QJsonValue(QJsonValue::Null) : deletionLink;
-    newLogEntry["imageLink"] = imageLink;
-    newLogEntry["localPath"] = originalFilePath.isEmpty()
-                                   ? QJsonValue(QJsonValue::Null)
-                                   : originalFilePath;
-    newLogEntry["timestamp"] = QDateTime::currentSecsSinceEpoch();
+    UploadedImage img;
+    img.channelName = channel->getName();
+    img.deletionLink = deletionLink;
+    img.imageLink = imageLink;
+    img.localPath = originalFilePath;
+    img.timestamp = QDateTime::currentSecsSinceEpoch();
+    entries.push_back(img);
     // channel name
     // deletion link (can be empty)
     // image link
     // local path to an image (can be empty)
     // timestamp
+    QJsonArray arr;
+    for (auto &entry : entries)
+    {
+        arr.append(entry.toJson());
+    }
     QSaveFile logSaveFile(logFileName);
     logSaveFile.open(QIODevice::WriteOnly | QIODevice::Text);
-    QJsonArray entries = QJsonDocument::fromJson(logs).array();
-    entries.push_back(newLogEntry);
-    logSaveFile.write(QJsonDocument(entries).toJson());
+    logSaveFile.write(QJsonDocument(arr).toJson());
     logSaveFile.commit();
-    //>>>>>>> e7508332ff1399a89424bfdc0997f979fd0c9acc:src/singletons/ImageUploader.cpp
 }
 
 // extracting link to either image or its deletion from response body
@@ -133,86 +162,30 @@ QString getLinkFromResponse(NetworkResult response, QString pattern)
 
 void ImageUploader::save()
 {
-    this->sm_->save();
 }
 
 UploadedImageModel *ImageUploader::createModel(QObject *parent)
 {
     auto *model = new UploadedImageModel(parent);
+    auto res = loadLogFile(getLogFilePath());
+
+    // Replace content of images_
+    auto len = this->images_.raw().size();
+    for (int i = 0; i < len; i++)
+    {
+        this->images_.removeAt(0);
+    }
+
+    std::vector<UploadedImage> vec = res.valueOr({});
+    for (const auto &img : vec)
+    {
+        this->images_.append(img);
+    }
+
     model->initialize(&this->images_);
     return model;
 }
 
-void ImageUploader::initialize(Settings &settings, const Paths &paths)
-{
-    auto logPath = (getSettings()->logPath.getValue().isEmpty()
-                        ? paths.messageLogDirectory
-                        : getSettings()->logPath);
-    const QString oldLogName = combinePath(logPath, "ImageUploader.json");
-
-    // read/write new one
-    const QString path = combinePath(logPath, "ImageUploader2.json");
-    this->sm_ = std::make_shared<pajlada::Settings::SettingManager>();
-    this->sm_->setPath(qPrintable(path));
-    this->sm_->setBackupEnabled(true);
-    this->sm_->setBackupSlots(9);
-
-    this->uploadedImagesSetting_ = std::make_unique<
-        pajlada::Settings::Setting<std::vector<UploadedImage>>>(
-        "/uploadedImages", this->sm_);
-    this->sm_->load();
-
-    // try to read old log
-    QFile oldLogFile(oldLogName);
-    bool isOldLogFileOkay =
-        oldLogFile.open(QIODevice::ReadOnly | QIODevice::Text);
-    if (isOldLogFileOkay)
-    {
-        auto data = oldLogFile.readAll();
-        rapidjson::Document doc;
-        doc.Parse(data.data(), data.size());
-        if (doc.HasParseError())
-        {
-            qCWarning(chatterinoCommon) << "Unable to read ImageUploader.json";
-            return;
-        }
-        std::vector<UploadedImage> temporary;
-        if (!doc.IsArray())
-        {
-            qCWarning(chatterinoCommon)
-                << "Unable to parse ImageUploader.json: not an array";
-            return;
-        }
-        if (!rj::getSafe(doc, temporary))
-        {
-            qCWarning(chatterinoCommon)
-                << "Unable to parse ImageUploader.json: getSafe failed";
-            return;
-        }
-        for (const auto &t : temporary)
-        {
-            this->images_.append(t);
-        }
-        oldLogFile.close();
-        oldLogFile.rename(combinePath(logPath, "ImageUploader.old.json"));
-    }
-
-    for (const auto &item : this->uploadedImagesSetting_->getValue())
-    {
-        this->images_.append(item);
-    }
-    this->signals_.addConnection(
-        this->images_.delayedItemsChanged.connect([this]() {
-            this->uploadedImagesSetting_->setValue(this->images_.raw());
-        }));
-
-    if (isOldLogFileOkay)
-    {
-        this->uploadedImagesSetting_->setValue(this->images_.raw());
-        this->sm_->save();
-    }
-}
-
 void ImageUploader::sendImageUploadRequest(RawImageData imageData,
                                            ChannelPtr channel,
                                            QPointer<ResizingTextEdit> textEdit)
diff --git a/src/singletons/imageuploader/ImageUploader.hpp b/src/singletons/imageuploader/ImageUploader.hpp
index d04dbd081..f104eff73 100644
--- a/src/singletons/imageuploader/ImageUploader.hpp
+++ b/src/singletons/imageuploader/ImageUploader.hpp
@@ -2,19 +2,17 @@
 
 #include "common/SignalVector.hpp"
 #include "common/Singleton.hpp"
-#include "pajlada/settings/setting.hpp"
-#include "pajlada/settings/settingmanager.hpp"
-#include "singletons/imageuploader/UploadedImage.hpp"
+#include "singletons/imageuploader/UploadedImageModel.hpp"
 
 #include <pajlada/signals/signalholder.hpp>
+#include <QJsonObject>
 #include <QMimeData>
 #include <QMutex>
-#include <qobject.h>
+#include <QObject>
 #include <QString>
 
 #include <memory>
 #include <queue>
-#include <vector>
 
 namespace chatterino {
 
@@ -23,12 +21,58 @@ class Channel;
 class NetworkResult;
 using ChannelPtr = std::shared_ptr<Channel>;
 
+struct UploadedImage {
+    QString channelName;
+    QString deletionLink;
+    QString imageLink;
+    QString localPath;
+    int64_t timestamp{};
+
+    UploadedImage() = default;
+    UploadedImage(QJsonObject obj)
+        : channelName(obj["channelName"].toString())
+        , imageLink(obj["imageLink"].toString())
+        , timestamp(obj["timestamp"].toInt())
+
+    {
+        auto del = obj["deletionLink"];
+        if (!del.isNull())
+        {
+            this->deletionLink = del.toString();
+        }
+        auto path = obj["localPath"];
+        if (!path.isNull())
+        {
+            this->localPath = path.toString();
+        }
+    }
+
+    QJsonObject toJson() const
+    {
+        QJsonObject out;
+        out["channelName"] = this->channelName;
+        out["deletionLink"] = this->deletionLink.isEmpty()
+                                  ? QJsonValue(QJsonValue::Null)
+                                  : this->deletionLink;
+        out["imageLink"] = this->imageLink;
+        out["localPath"] = this->localPath.isEmpty()
+                               ? QJsonValue(QJsonValue::Null)
+                               : this->localPath;
+
+        // without cast, this is ambiguous
+        out["timestamp"] = (qint64)this->timestamp;
+        return out;
+    }
+};
+
+class UploadedImageModel;
+
 struct RawImageData {
     QByteArray data;
     QString format;
     QString filePath;
 };
-class UploadedImageModel;
+
 class ImageUploader final : public Singleton
 {
 public:
@@ -43,7 +87,6 @@ public:
     void save() override;
     void upload(std::queue<RawImageData> images, ChannelPtr channel,
                 QPointer<ResizingTextEdit> outputTextEdit);
-    void initialize(Settings &settings, const Paths &paths) override;
     UploadedImageModel *createModel(QObject *parent);
 
 private:
@@ -58,15 +101,11 @@ private:
 
     void logToFile(const QString &originalFilePath, const QString &imageLink,
                    const QString &deletionLink, ChannelPtr channel);
-
     // These variables are only used from the main thread.
     QMutex uploadMutex_;
     std::queue<RawImageData> uploadQueue_;
 
-    std::shared_ptr<pajlada::Settings::SettingManager> sm_;
     SignalVector<UploadedImage> images_;
-    std::unique_ptr<pajlada::Settings::Setting<std::vector<UploadedImage>>>
-        uploadedImagesSetting_;
     pajlada::Signals::SignalHolder signals_;
 };
 }  // namespace chatterino
diff --git a/src/singletons/imageuploader/UploadedImage.hpp b/src/singletons/imageuploader/UploadedImage.hpp
deleted file mode 100644
index a2a5ad0fd..000000000
--- a/src/singletons/imageuploader/UploadedImage.hpp
+++ /dev/null
@@ -1,88 +0,0 @@
-#pragma once
-#include "util/RapidjsonHelpers.hpp"
-
-#include <QString>
-#include <Qt>
-
-#include <cstdint>
-
-namespace chatterino {
-struct UploadedImage {
-    QString channelName;
-    QString deletionLink;
-    QString imageLink;
-    QString localPath;
-    int64_t timestamp{};
-};
-}  // namespace chatterino
-
-namespace pajlada {
-template <>
-struct Serialize<chatterino::UploadedImage> {
-    static rapidjson::Value get(const chatterino::UploadedImage &value,
-                                rapidjson::Document::AllocatorType &a)
-    {
-        rapidjson::Value ret(rapidjson::kObjectType);
-
-        chatterino::rj::set(ret, "channelName", value.channelName, a);
-        chatterino::rj::set(ret, "imageLink", value.imageLink, a);
-        chatterino::rj::set(ret, "timestamp", value.timestamp, a);
-        chatterino::rj::set(ret, "localPath", value.localPath, a);
-        chatterino::rj::set(ret, "deletionLink", value.deletionLink, a);
-
-        return ret;
-    }
-};
-
-template <>
-struct Deserialize<chatterino::UploadedImage> {
-    static chatterino::UploadedImage get(const rapidjson::Value &value,
-                                         bool *error = nullptr)
-    {
-        chatterino::UploadedImage img;
-
-        if (!value.IsObject())
-        {
-            PAJLADA_REPORT_ERROR(error);
-            return img;
-        }
-
-        if (value["localPath"].IsNull())
-        {
-            img.localPath = QString();
-        }
-        else if (!chatterino::rj::getSafe(value, "localPath", img.localPath))
-        {
-            PAJLADA_REPORT_ERROR(error);
-            return img;
-        }
-        if (!chatterino::rj::getSafe(value, "imageLink", img.imageLink))
-        {
-            PAJLADA_REPORT_ERROR(error);
-            return img;
-        }
-        if (value["deletionLink"].IsNull())
-        {
-            img.deletionLink = QString();
-        }
-        else if (!chatterino::rj::getSafe(value, "deletionLink",
-                                          img.deletionLink))
-        {
-            PAJLADA_REPORT_ERROR(error);
-            return img;
-        }
-        if (!chatterino::rj::getSafe(value, "channelName", img.channelName))
-        {
-            PAJLADA_REPORT_ERROR(error);
-            return img;
-        }
-        if (!chatterino::rj::getSafe(value, "timestamp", img.timestamp))
-        {
-            PAJLADA_REPORT_ERROR(error);
-            return img;
-        }
-
-        return img;
-    }
-};
-}  // namespace pajlada