diff --git a/src/common/vfs.h b/src/common/vfs.h
index f4ea3d8fa..b7bd22098 100644
--- a/src/common/vfs.h
+++ b/src/common/vfs.h
@@ -190,7 +190,7 @@ public:
      * new placeholder shall supersede, for rename-replace actions with new downloads,
      * for example.
      */
-    virtual void convertToPlaceholder(
+    virtual Result<void, QString> convertToPlaceholder(
         const QString &filename,
         const SyncFileItem &item,
         const QString &replacesFile = QString()) = 0;
@@ -296,7 +296,7 @@ public:
     Result<void, QString> updateMetadata(const QString &, time_t, qint64, const QByteArray &) override { return {}; }
     Result<void, QString> createPlaceholder(const SyncFileItem &) override { return {}; }
     Result<void, QString> dehydratePlaceholder(const SyncFileItem &) override { return {}; }
-    void convertToPlaceholder(const QString &, const SyncFileItem &, const QString &) override {}
+    Result<void, QString> convertToPlaceholder(const QString &, const SyncFileItem &, const QString &) override { return {}; }
 
     bool needsMetadataUpdate(const SyncFileItem &) override { return false; }
     bool isDehydratedPlaceholder(const QString &) override { return false; }
diff --git a/src/libsync/owncloudpropagator.cpp b/src/libsync/owncloudpropagator.cpp
index f26dad05c..c576c93df 100644
--- a/src/libsync/owncloudpropagator.cpp
+++ b/src/libsync/owncloudpropagator.cpp
@@ -737,7 +737,9 @@ QString OwncloudPropagator::adjustRenamedPath(const QString &original) const
 bool OwncloudPropagator::updateMetadata(const SyncFileItem &item, const QString &localFolderPath, SyncJournalDb &journal, Vfs &vfs)
 {
     QString fsPath = localFolderPath + item.destination();
-    vfs.convertToPlaceholder(fsPath, item);
+    if (!vfs.convertToPlaceholder(fsPath, item)) {
+        return false;
+    }
     auto record = item.toSyncJournalFileRecordWithInode(fsPath);
     return journal.setFileRecord(record);
 }
diff --git a/src/libsync/propagatedownload.cpp b/src/libsync/propagatedownload.cpp
index 161b191df..06c0c6337 100644
--- a/src/libsync/propagatedownload.cpp
+++ b/src/libsync/propagatedownload.cpp
@@ -964,7 +964,11 @@ void PropagateDownloadFile::downloadFinished()
         preserveGroupOwnership(_tmpFile.fileName(), existingFile);
 
         // Make the file a hydrated placeholder if possible
-        propagator()->syncOptions()._vfs->convertToPlaceholder(_tmpFile.fileName(), *_item, fn);
+        const auto result = propagator()->syncOptions()._vfs->convertToPlaceholder(_tmpFile.fileName(), *_item, fn);
+        if (!result) {
+            done(SyncFileItem::NormalError, result.error());
+            return;
+        }
     }
 
     // Apply the remote permissions
diff --git a/src/libsync/syncengine.cpp b/src/libsync/syncengine.cpp
index 9c2dd8edc..7d6ae74d3 100644
--- a/src/libsync/syncengine.cpp
+++ b/src/libsync/syncengine.cpp
@@ -346,7 +346,12 @@ void OCC::SyncEngine::slotItemDiscovered(const OCC::SyncFileItemPtr &item)
 
             // Ensure it's a placeholder file on disk
             if (item->_type == ItemTypeFile) {
-                _syncOptions._vfs->convertToPlaceholder(filePath, *item);
+                const auto result = _syncOptions._vfs->convertToPlaceholder(filePath, *item);
+                if (!result) {
+                    item->_instruction = CSYNC_INSTRUCTION_ERROR;
+                    item->_errorString = tr("Could not update file : %1").arg(result.error());
+                    return;
+                }
             }
 
             // Update on-disk virtual file metadata
diff --git a/src/libsync/vfs/cfapi/vfs_cfapi.cpp b/src/libsync/vfs/cfapi/vfs_cfapi.cpp
index 4a73ad968..7a5da1e0e 100644
--- a/src/libsync/vfs/cfapi/vfs_cfapi.cpp
+++ b/src/libsync/vfs/cfapi/vfs_cfapi.cpp
@@ -149,16 +149,16 @@ Result<void, QString> VfsCfApi::dehydratePlaceholder(const SyncFileItem &item)
     return {};
 }
 
-void VfsCfApi::convertToPlaceholder(const QString &filename, const SyncFileItem &item, const QString &replacesFile)
+Result<void, QString> VfsCfApi::convertToPlaceholder(const QString &filename, const SyncFileItem &item, const QString &replacesFile)
 {
     const auto localPath = QDir::toNativeSeparators(filename);
     const auto replacesPath = QDir::toNativeSeparators(replacesFile);
 
     const auto handle = cfapi::handleForPath(localPath);
     if (cfapi::findPlaceholderInfo(handle)) {
-        cfapi::updatePlaceholderInfo(handle, item._modtime, item._size, item._fileId, replacesPath);
+        return cfapi::updatePlaceholderInfo(handle, item._modtime, item._size, item._fileId, replacesPath);
     } else {
-        cfapi::convertToPlaceholder(handle, item._modtime, item._size, item._fileId, replacesPath);
+        return cfapi::convertToPlaceholder(handle, item._modtime, item._size, item._fileId, replacesPath);
     }
 }
 
diff --git a/src/libsync/vfs/cfapi/vfs_cfapi.h b/src/libsync/vfs/cfapi/vfs_cfapi.h
index e4a4d0074..96dda52d4 100644
--- a/src/libsync/vfs/cfapi/vfs_cfapi.h
+++ b/src/libsync/vfs/cfapi/vfs_cfapi.h
@@ -43,7 +43,7 @@ public:
 
     Result<void, QString> createPlaceholder(const SyncFileItem &item) override;
     Result<void, QString> dehydratePlaceholder(const SyncFileItem &item) override;
-    void convertToPlaceholder(const QString &filename, const SyncFileItem &item, const QString &replacesFile) override;
+    Result<void, QString> convertToPlaceholder(const QString &filename, const SyncFileItem &item, const QString &replacesFile) override;
 
     bool needsMetadataUpdate(const SyncFileItem &) override;
     bool isDehydratedPlaceholder(const QString &filePath) override;
diff --git a/src/libsync/vfs/suffix/vfs_suffix.cpp b/src/libsync/vfs/suffix/vfs_suffix.cpp
index 40a7519a7..f3858e8a2 100644
--- a/src/libsync/vfs/suffix/vfs_suffix.cpp
+++ b/src/libsync/vfs/suffix/vfs_suffix.cpp
@@ -122,9 +122,10 @@ Result<void, QString> VfsSuffix::dehydratePlaceholder(const SyncFileItem &item)
     return {};
 }
 
-void VfsSuffix::convertToPlaceholder(const QString &, const SyncFileItem &, const QString &)
+Result<void, QString> VfsSuffix::convertToPlaceholder(const QString &, const SyncFileItem &, const QString &)
 {
     // Nothing necessary
+    return {};
 }
 
 bool VfsSuffix::isDehydratedPlaceholder(const QString &filePath)
diff --git a/src/libsync/vfs/suffix/vfs_suffix.h b/src/libsync/vfs/suffix/vfs_suffix.h
index 3feca6ea0..4aa513c03 100644
--- a/src/libsync/vfs/suffix/vfs_suffix.h
+++ b/src/libsync/vfs/suffix/vfs_suffix.h
@@ -41,7 +41,7 @@ public:
 
     Result<void, QString> createPlaceholder(const SyncFileItem &item) override;
     Result<void, QString> dehydratePlaceholder(const SyncFileItem &item) override;
-    void convertToPlaceholder(const QString &filename, const SyncFileItem &item, const QString &) override;
+    Result<void, QString> convertToPlaceholder(const QString &filename, const SyncFileItem &item, const QString &) override;
 
     bool needsMetadataUpdate(const SyncFileItem &) override { return false; }
     bool isDehydratedPlaceholder(const QString &filePath) override;