diff --git a/src/base/bittorrent/torrenthandle.cpp b/src/base/bittorrent/torrenthandle.cpp
index 93aa75d60..2da728bcf 100644
--- a/src/base/bittorrent/torrenthandle.cpp
+++ b/src/base/bittorrent/torrenthandle.cpp
@@ -1402,6 +1402,7 @@ void TorrentHandle::setTrackerLogin(const QString &username, const QString &pass
 
 void TorrentHandle::renameFile(int index, const QString &name)
 {
+    m_oldPath[LTFileIndex {index}].push_back(filePath(index));
     ++m_renameCount;
     qDebug() << Q_FUNC_INFO << index << name;
     m_nativeHandle.rename_file(index, Utils::Fs::toNativePath(name).toStdString());
@@ -1685,33 +1686,42 @@ void TorrentHandle::handleFastResumeRejectedAlert(const libtorrent::fastresume_r
 
 void TorrentHandle::handleFileRenamedAlert(const libtorrent::file_renamed_alert *p)
 {
-#if LIBTORRENT_VERSION_NUM < 10100
-    QString newName = Utils::Fs::fromNativePath(QString::fromStdString(p->name));
-#else
-    QString newName = Utils::Fs::fromNativePath(p->new_name());
-#endif
-
-    // TODO: Check this!
-    if (filesCount() > 1) {
-        // Check if folders were renamed
-        QStringList oldPathParts = m_torrentInfo.origFilePath(p->index).split('/');
-        oldPathParts.removeLast();
-        QString oldPath = oldPathParts.join('/');
-        QStringList newPathParts = newName.split('/');
-        newPathParts.removeLast();
-        QString newPath = newPathParts.join('/');
-        if (!newPathParts.isEmpty() && (oldPath != newPath)) {
-            qDebug("oldPath(%s) != newPath(%s)", qUtf8Printable(oldPath), qUtf8Printable(newPath));
-            oldPath = QString("%1/%2").arg(savePath(true), oldPath);
-            qDebug("Detected folder renaming, attempt to delete old folder: %s", qUtf8Printable(oldPath));
-            QDir().rmpath(oldPath);
-        }
-    }
-
     // We don't really need to call updateStatus() in this place.
     // All we need to do is make sure we have a valid instance of the TorrentInfo object.
     m_torrentInfo = TorrentInfo {m_nativeHandle.torrent_file()};
 
+    // remove empty leftover folders
+    // for example renaming "a/b/c" to "d/b/c", then folders "a/b" and "a" will
+    // be removed if they are empty
+    const QString oldFilePath = m_oldPath[LTFileIndex {p->index}].takeFirst();
+    const QString newFilePath = Utils::Fs::fromNativePath(p->new_name());
+
+    if (m_oldPath[LTFileIndex {p->index}].isEmpty())
+        m_oldPath.remove(LTFileIndex {p->index});
+
+    QVector<QStringRef> oldPathParts = oldFilePath.splitRef('/', QString::SkipEmptyParts);
+    oldPathParts.removeLast();  // drop file name part
+    QVector<QStringRef> newPathParts = newFilePath.splitRef('/', QString::SkipEmptyParts);
+    newPathParts.removeLast();  // drop file name part
+
+#if defined(Q_OS_WIN)
+    const Qt::CaseSensitivity caseSensitivity = Qt::CaseInsensitive;
+#else
+    const Qt::CaseSensitivity caseSensitivity = Qt::CaseSensitive;
+#endif
+
+    int pathIdx = 0;
+    while ((pathIdx < oldPathParts.size()) && (pathIdx < newPathParts.size())) {
+        if (oldPathParts[pathIdx].compare(newPathParts[pathIdx], caseSensitivity) != 0)
+            break;
+        ++pathIdx;
+    }
+
+    for (int i = (oldPathParts.size() - 1); i >= pathIdx; --i) {
+        QDir().rmdir(savePath() + Utils::String::join(oldPathParts, QLatin1String("/")));
+        oldPathParts.removeLast();
+    }
+
     --m_renameCount;
     while (!isMoveInProgress() && (m_renameCount == 0) && !m_moveFinishedTriggers.isEmpty())
         m_moveFinishedTriggers.takeFirst()();
@@ -1719,7 +1729,13 @@ void TorrentHandle::handleFileRenamedAlert(const libtorrent::file_renamed_alert
 
 void TorrentHandle::handleFileRenameFailedAlert(const libtorrent::file_rename_failed_alert *p)
 {
-    Q_UNUSED(p);
+    LogMsg(tr("File rename failed. Torrent: \"%1\", file: \"%2\", reason: \"%3\"")
+        .arg(name(), filePath(p->index)
+             , QString::fromStdString(p->error.message())), Log::WARNING);
+
+    m_oldPath[LTFileIndex {p->index}].removeFirst();
+    if (m_oldPath[LTFileIndex {p->index}].isEmpty())
+        m_oldPath.remove(LTFileIndex {p->index});
 
     --m_renameCount;
     while (!isMoveInProgress() && (m_renameCount == 0) && !m_moveFinishedTriggers.isEmpty())
diff --git a/src/base/bittorrent/torrenthandle.h b/src/base/bittorrent/torrenthandle.h
index 425e688d4..c9d9d9a67 100644
--- a/src/base/bittorrent/torrenthandle.h
+++ b/src/base/bittorrent/torrenthandle.h
@@ -385,6 +385,12 @@ namespace BitTorrent
     private:
         typedef boost::function<void ()> EventTrigger;
 
+#if (LIBTORRENT_VERSION_NUM < 10200)
+        using LTFileIndex = int;
+#else
+        using LTFileIndex = lt::file_index_t;
+#endif
+
         void updateStatus();
         void updateStatus(const libtorrent::torrent_status &nativeStatus);
         void updateState();
@@ -446,6 +452,10 @@ namespace BitTorrent
         QQueue<EventTrigger> m_moveFinishedTriggers;
         int m_renameCount;
 
+        // Until libtorrent provide an "old_name" field in `file_renamed_alert`
+        // we will rely on this workaround to remove empty leftover folders
+        QHash<LTFileIndex, QVector<QString>> m_oldPath;
+
         bool m_useAutoTMM;
 
         // Persistent data
diff --git a/src/base/utils/string.cpp b/src/base/utils/string.cpp
index 85b5b9191..59c07031b 100644
--- a/src/base/utils/string.cpp
+++ b/src/base/utils/string.cpp
@@ -213,3 +213,14 @@ TriStateBool Utils::String::parseTriStateBool(const QString &string)
         return TriStateBool::False;
     return TriStateBool::Undefined;
 }
+
+QString Utils::String::join(const QVector<QStringRef> &strings, const QString &separator)
+{
+    if (strings.empty())
+        return {};
+
+    QString ret = strings[0].toString();
+    for (int i = 1; i < strings.count(); ++i)
+        ret += (separator + strings[i]);
+    return ret;
+}
diff --git a/src/base/utils/string.h b/src/base/utils/string.h
index 5a1088622..3f15322da 100644
--- a/src/base/utils/string.h
+++ b/src/base/utils/string.h
@@ -31,6 +31,7 @@
 #define UTILS_STRING_H
 
 #include <QString>
+#include <QVector>
 
 class QByteArray;
 class QLatin1String;
@@ -70,6 +71,8 @@ namespace Utils
 
         bool parseBool(const QString &string, const bool defaultValue);
         TriStateBool parseTriStateBool(const QString &string);
+
+        QString join(const QVector<QStringRef> &strings, const QString &separator);
     }
 }
 
diff --git a/src/gui/torrentcontenttreeview.cpp b/src/gui/torrentcontenttreeview.cpp
index 3e65b70fd..285d3f568 100644
--- a/src/gui/torrentcontenttreeview.cpp
+++ b/src/gui/torrentcontenttreeview.cpp
@@ -205,15 +205,6 @@ void TorrentContentTreeView::renameSelectedFile(BitTorrent::TorrentHandle *torre
         if (needForceRecheck)
             torrent->forceRecheck();
 
-        // Remove old folder
-        const QString oldFullPath = torrent->savePath(true) + oldPath;
-        int timeout = 10;
-        while (!QDir().rmpath(oldFullPath) && (timeout > 0)) {
-            // FIXME: We should not sleep here (freezes the UI for 1 second)
-            QThread::msleep(100);
-            --timeout;
-        }
-
         model->setData(modelIndex, newName);
     }
 }