diff --git a/src/core/musicstorage.h b/src/core/musicstorage.h
index 33217f9fd..bc1813b18 100644
--- a/src/core/musicstorage.h
+++ b/src/core/musicstorage.h
@@ -36,6 +36,13 @@ public:
     Role_FreeSpace,
   };
 
+  // Values are saved in the database - don't change
+  enum TranscodeMode {
+    Transcode_Always = 1,
+    Transcode_Never = 2,
+    Transcode_Unsupported = 3,
+  };
+
   typedef boost::function<void (float progress)> ProgressFunction;
 
   struct CopyJob {
@@ -53,6 +60,10 @@ public:
 
   virtual QString LocalPath() const { return QString(); }
 
+  virtual TranscodeMode GetTranscodeMode() const { return Transcode_Never; }
+  virtual Song::FileType GetTranscodeFormat() const { return Song::Type_Unknown; }
+  virtual QList<Song::FileType> SupportedFiletypes() { return QList<Song::FileType>(); }
+
   virtual void StartCopy() {}
   virtual bool CopyToStorage(const CopyJob& job) = 0;
   virtual void FinishCopy(bool success) {}
diff --git a/src/core/organise.cpp b/src/core/organise.cpp
index 661b83567..773e2ee33 100644
--- a/src/core/organise.cpp
+++ b/src/core/organise.cpp
@@ -33,18 +33,24 @@ Organise::Organise(TaskManager* task_manager,
                    const QStringList& files, bool eject_after)
                      : thread_(NULL),
                        task_manager_(task_manager),
+                       transcoder_(new Transcoder(this)),
                        destination_(destination),
                        format_(format),
                        copy_(copy),
                        overwrite_(overwrite),
-                       files_(files),
                        eject_after_(eject_after),
+                       task_count_(files.count()),
+                       transcode_suffix_(1),
                        started_(false),
                        task_id_(0),
                        progress_(0),
                        song_progress_(0)
 {
   original_thread_ = thread();
+
+  foreach (const QString& filename, files) {
+    tasks_pending_ << Task(filename);
+  }
 }
 
 void Organise::Start() {
@@ -56,6 +62,7 @@ void Organise::Start() {
 
   thread_ = new QThread;
   connect(thread_, SIGNAL(started()), SLOT(ProcessSomeFiles()));
+  connect(transcoder_, SIGNAL(JobComplete(QString,bool)), SLOT(FileTranscoded(QString,bool)));
 
   moveToThread(thread_);
   thread_->start();
@@ -63,12 +70,21 @@ void Organise::Start() {
 
 void Organise::ProcessSomeFiles() {
   if (!started_) {
+    transcode_temp_name_.open();
+    supported_filetypes_ = destination_->SupportedFiletypes();
+
     destination_->StartCopy();
     started_ = true;
   }
 
   // None left?
-  if (progress_ >= files_.count()) {
+  if (tasks_pending_.isEmpty()) {
+    if (!tasks_transcoding_.isEmpty()) {
+      // Just wait - FileTranscoded will start us off again in a little while
+      qDebug() << "Waiting for transcoding jobs";
+      return;
+    }
+
     UpdateProgress();
 
     destination_->FinishCopy(files_with_errors_.isEmpty());
@@ -89,34 +105,75 @@ void Organise::ProcessSomeFiles() {
     return;
   }
 
-  QDir dir;
-
   // We process files in batches so we can be cancelled part-way through.
-
-  const int n = qMin(files_.count(), progress_ + kBatchSize);
-  for ( ; progress_<n ; ++progress_) {
+  for (int i=0 ; i<kBatchSize ; ++i) {
     SetSongProgress(0);
 
-    const QString filename = files_[progress_];
+    if (tasks_pending_.isEmpty())
+      break;
+
+    Task task = tasks_pending_.takeFirst();
+    qDebug() << "Processing" << task.filename_;
 
     // Is it a directory?
-    if (QFileInfo(filename).isDir()) {
-      QDir dir(filename);
+    if (QFileInfo(task.filename_).isDir()) {
+      QDir dir(task.filename_);
       foreach (const QString& entry, dir.entryList(
           QDir::Dirs | QDir::Files | QDir::NoDotAndDotDot | QDir::Readable)) {
-        files_ << filename + "/" + entry;
+        tasks_pending_ << Task(task.filename_ + "/" + entry);
+        task_count_ ++;
       }
       continue;
     }
 
     // Read metadata from the file
     Song song;
-    song.InitFromFile(filename, -1);
+    song.InitFromFile(task.filename_, -1);
     if (!song.is_valid())
       continue;
 
+    // Maybe this file is one that's been transcoded already?
+    if (!task.transcoded_filename_.isEmpty()) {
+      qDebug() << "This file has already been transcoded";
+
+      // Set the new filetype on the song so the formatter gets it right
+      song.set_filetype(task.new_filetype_);
+
+      // Fiddle the filename extension as well to match the new type
+      song.set_filename(song.filename().section('.', 0, -2) + "." + task.new_extension_);
+      song.set_basefilename(song.basefilename().section('.', 0, -2) + "." + task.new_extension_);
+
+      // Have to set this to the size of the new file or else funny stuff happens
+      song.set_filesize(QFileInfo(task.transcoded_filename_).size());
+    } else {
+      // Figure out if we need to transcode it
+      Song::FileType dest_type = CheckTranscode(song.filetype());
+      if (dest_type != Song::Type_Unknown) {
+        // Get the preset
+        TranscoderPreset preset = Transcoder::PresetForFileType(dest_type);
+        qDebug() << "Transcoding with" << preset.name_;
+
+        // Get a temporary name for the transcoded file
+        task.transcoded_filename_ = transcode_temp_name_.fileName() + "-" +
+                                    QString::number(transcode_suffix_++);
+        task.new_extension_ = preset.extension_;
+        task.new_filetype_ = dest_type;
+        tasks_transcoding_[task.filename_] = task;
+
+        qDebug() << "Transcoding to" << task.transcoded_filename_;
+
+        // Start the transcoding - this will happen in the background and
+        // FileTranscoded() will get called when it's done.  At that point the
+        // task will get re-added to the pending queue with the new filename.
+        transcoder_->AddJob(task.filename_, preset, task.transcoded_filename_);
+        transcoder_->Start();
+        continue;
+      }
+    }
+
     MusicStorage::CopyJob job;
-    job.source_ = filename;
+    job.source_ = task.transcoded_filename_.isEmpty() ?
+                  task.filename_ : task.transcoded_filename_;
     job.destination_ = format_.GetFilenameForSong(song);
     job.metadata_ = song;
     job.overwrite_ = overwrite_;
@@ -124,14 +181,47 @@ void Organise::ProcessSomeFiles() {
     job.progress_ = boost::bind(&Organise::SetSongProgress, this, _1);
 
     if (!destination_->CopyToStorage(job)) {
-      files_with_errors_ << filename;
+      files_with_errors_ << task.filename_;
     }
+
+    progress_++;
   }
   SetSongProgress(0);
 
   QTimer::singleShot(0, this, SLOT(ProcessSomeFiles()));
 }
 
+Song::FileType Organise::CheckTranscode(Song::FileType original_type) const {
+  if (original_type == Song::Type_Stream)
+    return Song::Type_Unknown;
+
+  const MusicStorage::TranscodeMode mode = destination_->GetTranscodeMode();
+  const Song::FileType format = destination_->GetTranscodeFormat();
+
+  switch (mode) {
+    case MusicStorage::Transcode_Never:
+      return Song::Type_Unknown;
+
+    case MusicStorage::Transcode_Always:
+      if (original_type == format)
+        return Song::Type_Unknown;
+      return format;
+
+    case MusicStorage::Transcode_Unsupported:
+      if (supported_filetypes_.isEmpty() || supported_filetypes_.contains(original_type))
+        return Song::Type_Unknown;
+
+      if (format != Song::Type_Unknown)
+        return format;
+
+      // The user hasn't visited the device properties page yet to set a
+      // preferred format for the device, so we have to pick the best
+      // available one.
+      return Transcoder::PickBestFormat(supported_filetypes_);
+  }
+  return Song::Type_Unknown;
+}
+
 void Organise::SetSongProgress(float progress) {
   song_progress_ = qBound(0, int(progress * 100), 99);
   UpdateProgress();
@@ -139,6 +229,18 @@ void Organise::SetSongProgress(float progress) {
 
 void Organise::UpdateProgress() {
   const int progress = progress_ * 100 + song_progress_;
-  const int total = files_.count() * 100;
+  const int total = task_count_ * 100;
   task_manager_->SetTaskProgress(task_id_, progress, total);
 }
+
+void Organise::FileTranscoded(const QString& filename, bool success) {
+  qDebug() << "File finished" << filename << success;
+
+  Task task = tasks_transcoding_.take(filename);
+  if (!success) {
+    files_with_errors_ << filename;
+  } else {
+    tasks_pending_ << task;
+  }
+  QTimer::singleShot(0, this, SLOT(ProcessSomeFiles()));
+}
diff --git a/src/core/organise.h b/src/core/organise.h
index 969590e45..ad4e950b1 100644
--- a/src/core/organise.h
+++ b/src/core/organise.h
@@ -18,10 +18,12 @@
 #define ORGANISE_H
 
 #include <QObject>
+#include <QTemporaryFile>
 
 #include <boost/shared_ptr.hpp>
 
 #include "organiseformat.h"
+#include "transcoder/transcoder.h"
 
 class MusicStorage;
 class TaskManager;
@@ -44,20 +46,41 @@ signals:
 
 private slots:
   void ProcessSomeFiles();
-  void SetSongProgress(float progress);
-  void UpdateProgress();
+  void FileTranscoded(const QString& filename, bool success);
 
 private:
+  void SetSongProgress(float progress);
+  void UpdateProgress();
+  Song::FileType CheckTranscode(Song::FileType original_type) const;
+
+private:
+  struct Task {
+    Task(const QString& filename = QString()) : filename_(filename) {}
+
+    QString filename_;
+    QString transcoded_filename_;
+    QString new_extension_;
+    Song::FileType new_filetype_;
+  };
+
   QThread* thread_;
   QThread* original_thread_;
   TaskManager* task_manager_;
+  Transcoder* transcoder_;
   boost::shared_ptr<MusicStorage> destination_;
+  QList<Song::FileType> supported_filetypes_;
 
   const OrganiseFormat format_;
   const bool copy_;
   const bool overwrite_;
-  QStringList files_;
   const bool eject_after_;
+  int task_count_;
+
+  QTemporaryFile transcode_temp_name_;
+  int transcode_suffix_;
+
+  QList<Task> tasks_pending_;
+  QMap<QString, Task> tasks_transcoding_;
 
   bool started_;
 
diff --git a/src/devices/connecteddevice.cpp b/src/devices/connecteddevice.cpp
index af822d007..98e4a2f98 100644
--- a/src/devices/connecteddevice.cpp
+++ b/src/devices/connecteddevice.cpp
@@ -94,3 +94,15 @@ void ConnectedDevice::FinishCopy(bool) {
 void ConnectedDevice::FinishDelete(bool) {
   lister_->UpdateDeviceFreeSpace(unique_id_);
 }
+
+MusicStorage::TranscodeMode ConnectedDevice::GetTranscodeMode() const {
+  int index = manager_->FindDeviceById(unique_id_);
+  return MusicStorage::TranscodeMode(
+      manager_->index(index).data(DeviceManager::Role_TranscodeMode).toInt());
+}
+
+Song::FileType ConnectedDevice::GetTranscodeFormat() const {
+  int index = manager_->FindDeviceById(unique_id_);
+  return Song::FileType(
+      manager_->index(index).data(DeviceManager::Role_TranscodeFormat).toInt());
+}
diff --git a/src/devices/connecteddevice.h b/src/devices/connecteddevice.h
index 0b290aa26..eabab8ed7 100644
--- a/src/devices/connecteddevice.h
+++ b/src/devices/connecteddevice.h
@@ -44,7 +44,8 @@ public:
 
   virtual void Init() = 0;
 
-  virtual QList<Song::FileType> SupportedFiletypes() { return QList<Song::FileType>(); }
+  virtual TranscodeMode GetTranscodeMode() const;
+  virtual Song::FileType GetTranscodeFormat() const;
 
   DeviceLister* lister() const { return lister_; }
   QString unique_id() const { return unique_id_; }
diff --git a/src/devices/devicedatabasebackend.cpp b/src/devices/devicedatabasebackend.cpp
index 9d979275b..de401d831 100644
--- a/src/devices/devicedatabasebackend.cpp
+++ b/src/devices/devicedatabasebackend.cpp
@@ -52,7 +52,7 @@ DeviceDatabaseBackend::DeviceList DeviceDatabaseBackend::GetAllDevices() {
     dev.friendly_name_ = q.value(2).toString();
     dev.size_ = q.value(3).toLongLong();
     dev.icon_name_ = q.value(4).toString();
-    dev.transcode_mode_ = TranscodeMode(q.value(5).toInt());
+    dev.transcode_mode_ = MusicStorage::TranscodeMode(q.value(5).toInt());
     dev.transcode_format_ = Song::FileType(q.value(6).toInt());
     ret << dev;
   }
@@ -118,7 +118,7 @@ void DeviceDatabaseBackend::RemoveDevice(int id) {
 
 void DeviceDatabaseBackend::SetDeviceOptions(int id,
     const QString &friendly_name, const QString &icon_name,
-    TranscodeMode mode, Song::FileType format) {
+    MusicStorage::TranscodeMode mode, Song::FileType format) {
   QMutexLocker l(db_->Mutex());
   QSqlDatabase db(db_->Connect());
 
diff --git a/src/devices/devicedatabasebackend.h b/src/devices/devicedatabasebackend.h
index b9eca4106..109439ea1 100644
--- a/src/devices/devicedatabasebackend.h
+++ b/src/devices/devicedatabasebackend.h
@@ -21,6 +21,7 @@
 
 #include <boost/shared_ptr.hpp>
 
+#include "core/musicstorage.h"
 #include "core/song.h"
 
 class Database;
@@ -31,13 +32,6 @@ class DeviceDatabaseBackend : public QObject {
 public:
   Q_INVOKABLE DeviceDatabaseBackend(QObject* parent = 0);
 
-  // Values are saved in the database - don't change
-  enum TranscodeMode {
-    Transcode_Always = 1,
-    Transcode_Never = 2,
-    Transcode_Unsupported = 3,
-  };
-
   struct Device {
     Device() : id_(-1) {}
 
@@ -47,7 +41,7 @@ public:
     quint64 size_;
     QString icon_name_;
 
-    TranscodeMode transcode_mode_;
+    MusicStorage::TranscodeMode transcode_mode_;
     Song::FileType transcode_format_;
   };
   typedef QList<Device> DeviceList;
@@ -63,7 +57,7 @@ public:
 
   void SetDeviceOptions(int id,
       const QString& friendly_name, const QString& icon_name,
-      TranscodeMode mode, Song::FileType format);
+      MusicStorage::TranscodeMode mode, Song::FileType format);
 
 private:
   boost::shared_ptr<Database> db_;
diff --git a/src/devices/devicemanager.cpp b/src/devices/devicemanager.cpp
index 18f6171f3..aa4404b47 100644
--- a/src/devices/devicemanager.cpp
+++ b/src/devices/devicemanager.cpp
@@ -60,7 +60,7 @@ const int DeviceManager::kDeviceIconOverlaySize = 16;
 
 DeviceManager::DeviceInfo::DeviceInfo()
   : database_id_(-1),
-    transcode_mode_(DeviceDatabaseBackend::Transcode_Unsupported),
+    transcode_mode_(MusicStorage::Transcode_Unsupported),
     transcode_format_(Song::Type_Unknown),
     task_percentage_(-1)
 {
@@ -618,7 +618,7 @@ void DeviceManager::Forget(int row) {
 
 void DeviceManager::SetDeviceOptions(int row,
     const QString& friendly_name, const QString& icon_name,
-    DeviceDatabaseBackend::TranscodeMode mode, Song::FileType format) {
+    MusicStorage::TranscodeMode mode, Song::FileType format) {
   DeviceInfo& info = devices_[row];
   info.friendly_name_ = friendly_name;
   info.LoadIcon(QVariantList() << icon_name, friendly_name);
@@ -676,6 +676,8 @@ void DeviceManager::TasksChanged() {
     DeviceInfo& info = devices_[index.row()];
     info.task_percentage_ = -1;
     emit dataChanged(index, index);
+
+    active_tasks_.remove(active_tasks_.key(index));
   }
 }
 
diff --git a/src/devices/devicemanager.h b/src/devices/devicemanager.h
index cf4dc72bb..b870c3e8b 100644
--- a/src/devices/devicemanager.h
+++ b/src/devices/devicemanager.h
@@ -85,7 +85,7 @@ public:
 
   void SetDeviceOptions(int row,
       const QString& friendly_name, const QString& icon_name,
-      DeviceDatabaseBackend::TranscodeMode mode, Song::FileType format);
+      MusicStorage::TranscodeMode mode, Song::FileType format);
 
   // QAbstractListModel
   int rowCount(const QModelIndex &parent) const;
@@ -151,7 +151,7 @@ private:
     QString icon_name_;
     QIcon icon_;
 
-    DeviceDatabaseBackend::TranscodeMode transcode_mode_;
+    MusicStorage::TranscodeMode transcode_mode_;
     Song::FileType transcode_format_;
 
     int task_percentage_;
diff --git a/src/devices/deviceproperties.cpp b/src/devices/deviceproperties.cpp
index 36156fd4d..463bf7e1a 100644
--- a/src/devices/deviceproperties.cpp
+++ b/src/devices/deviceproperties.cpp
@@ -187,18 +187,18 @@ void DeviceProperties::UpdateFormats() {
       manager_->GetConnectedDevice(index_.row());
 
   // Transcode mode
-  DeviceDatabaseBackend::TranscodeMode mode = DeviceDatabaseBackend::TranscodeMode(
+  MusicStorage::TranscodeMode mode = MusicStorage::TranscodeMode(
       index_.data(DeviceManager::Role_TranscodeMode).toInt());
   switch (mode) {
-    case DeviceDatabaseBackend::Transcode_Always:
+    case MusicStorage::Transcode_Always:
       ui_->transcode_all->setChecked(true);
       break;
 
-    case DeviceDatabaseBackend::Transcode_Never:
+    case MusicStorage::Transcode_Never:
       ui_->transcode_off->setChecked(true);
       break;
 
-    case DeviceDatabaseBackend::Transcode_Unsupported:
+    case MusicStorage::Transcode_Unsupported:
     default:
       ui_->transcode_unsupported->setChecked(true);
       break;
@@ -238,13 +238,13 @@ void DeviceProperties::accept() {
   QDialog::accept();
 
   // Transcode mode
-  DeviceDatabaseBackend::TranscodeMode mode = DeviceDatabaseBackend::Transcode_Unsupported;
+  MusicStorage::TranscodeMode mode = MusicStorage::Transcode_Unsupported;
   if (ui_->transcode_all->isChecked())
-    mode = DeviceDatabaseBackend::Transcode_Always;
+    mode = MusicStorage::Transcode_Always;
   else if (ui_->transcode_off->isChecked())
-    mode = DeviceDatabaseBackend::Transcode_Never;
+    mode = MusicStorage::Transcode_Never;
   else if (ui_->transcode_unsupported->isChecked())
-    mode = DeviceDatabaseBackend::Transcode_Unsupported;
+    mode = MusicStorage::Transcode_Unsupported;
 
   // Transcode format
   Song::FileType format = Song::FileType(ui_->transcode_format->itemData(
@@ -288,23 +288,7 @@ void DeviceProperties::UpdateFormatsFinished() {
   if (preset.type_ == Song::Type_Unknown) {
     // The user hasn't chosen a format for this device yet, so work our way down
     // a list of some preferred formats, picking the first one that is supported
-    QList<Song::FileType> best_formats;
-    best_formats << Song::Type_Mpeg;
-    best_formats << Song::Type_OggVorbis;
-    best_formats << Song::Type_Asf;
-
-    foreach (Song::FileType type, best_formats) {
-      if (list.isEmpty() || list.contains(type)) {
-        preset = Transcoder::PresetForFileType(type);
-        break;
-      }
-    }
-
-    if (preset.type_ == Song::Type_Unknown) {
-      // Still haven't found a good format - pick the first one that the
-      // device advertises.
-      preset = Transcoder::PresetForFileType(list[0]);
-    }
+    preset = Transcoder::PresetForFileType(Transcoder::PickBestFormat(list));
   }
   ui_->transcode_format->setCurrentIndex(ui_->transcode_format->findText(preset.name_));
 
diff --git a/src/devices/mtpdevice.cpp b/src/devices/mtpdevice.cpp
index 71523b575..34c039ecd 100644
--- a/src/devices/mtpdevice.cpp
+++ b/src/devices/mtpdevice.cpp
@@ -84,6 +84,9 @@ static int ProgressCallback(uint64_t const sent, uint64_t const total,
 }
 
 bool MtpDevice::CopyToStorage(const CopyJob& job) {
+  if (!connection_->is_valid())
+    return false;
+
   // Convert metadata
   LIBMTP_track_t track;
   job.metadata_.ToMTP(&track);
@@ -165,6 +168,11 @@ QList<Song::FileType> MtpDevice::SupportedFiletypes() {
 
   QMutexLocker l(&db_busy_);
   MtpConnection connection(url_.host());
+  if (!connection.is_valid()) {
+    qWarning() << "Error connecting to MTP device, couldn't get list of supported filetypes";
+    return ret;
+  }
+
   if (LIBMTP_Get_Supported_Filetypes(connection.device(), &list, &length)
       || !list || !length)
     return ret;
diff --git a/src/transcoder/transcoder.cpp b/src/transcoder/transcoder.cpp
index 252d5d73a..684e80c2a 100644
--- a/src/transcoder/transcoder.cpp
+++ b/src/transcoder/transcoder.cpp
@@ -206,6 +206,23 @@ TranscoderPreset Transcoder::PresetForFileType(Song::FileType type) {
   }
 }
 
+Song::FileType Transcoder::PickBestFormat(QList<Song::FileType> supported) {
+  if (supported.isEmpty())
+    return Song::Type_Unknown;
+
+  QList<Song::FileType> best_formats;
+  best_formats << Song::Type_Mpeg;
+  best_formats << Song::Type_OggVorbis;
+  best_formats << Song::Type_Asf;
+
+  foreach (Song::FileType type, best_formats) {
+    if (supported.isEmpty() || supported.contains(type))
+      return type;
+  }
+
+  return supported[0];
+}
+
 void Transcoder::AddJob(const QString& input,
                         const TranscoderPreset& preset,
                         const QString& output) {
diff --git a/src/transcoder/transcoder.h b/src/transcoder/transcoder.h
index af75969d2..9e4edf8cd 100644
--- a/src/transcoder/transcoder.h
+++ b/src/transcoder/transcoder.h
@@ -55,6 +55,7 @@ class Transcoder : public QObject {
 
   static TranscoderPreset PresetForFileType(Song::FileType type);
   static QList<TranscoderPreset> GetAllPresets();
+  static Song::FileType PickBestFormat(QList<Song::FileType> supported);
 
   int max_threads() const { return max_threads_; }