diff --git a/src/lib/common/Settings.cpp b/src/lib/common/Settings.cpp
index 544fde13c..4c6e49d0d 100644
--- a/src/lib/common/Settings.cpp
+++ b/src/lib/common/Settings.cpp
@@ -20,45 +20,42 @@ Settings *Settings::instance()
 
 void Settings::setSettingFile(const QString &settingsFile)
 {
-  if (instance()->m_portableSettingsFile == settingsFile) {
-    qDebug().noquote() << "settings file already in use";
+  if (instance()->settingsFile() == settingsFile) {
+    qDebug("settings file already set, skipping");
     return;
   }
 
-  instance()->m_portableSettingsFile = settingsFile;
   if (instance()->m_settings)
     instance()->m_settings->deleteLater();
-  instance()->m_settings = new QSettings(instance()->m_portableSettingsFile, QSettings::IniFormat);
-  instance()->m_settingsProxy->load(instance()->m_portableSettingsFile);
-  qInfo().noquote() << "settings file:" << instance()->m_settings->fileName();
+
+  instance()->m_settings = new QSettings(settingsFile, QSettings::IniFormat);
+  instance()->m_settingsProxy->load(settingsFile);
+  qInfo().noquote() << "settings file changed:" << instance()->m_settings->fileName();
 }
 
 Settings::Settings(QObject *parent) : QObject(parent)
 {
   QString fileToLoad;
 #ifdef Q_OS_WIN
-  m_portableSettingsFile = m_portableSettingsFile.arg(QCoreApplication::applicationDirPath(), kAppName);
-  if (QFile(m_portableSettingsFile).exists()) {
-    fileToLoad = m_portableSettingsFile;
-    m_settings = new QSettings(fileToLoad, QSettings::IniFormat);
-  } else {
-    m_settings = new QSettings(QSettings::NativeFormat, QSettings::UserScope, kAppName, kAppName);
-  }
+  const auto portableFile = portableSettingsFile();
+  qDebug().noquote() << "checking for portable settings file at:" << portableFile;
+  if (QFile(portableFile).exists())
+    fileToLoad = portableFile;
 #else
   if (!qEnvironmentVariable("XDG_CONFIG_HOME").isEmpty())
     fileToLoad = QStringLiteral("%1/%2/%2.conf").arg(qEnvironmentVariable("XDG_CONFIG_HOME"), kAppName);
+#endif
   else if (QFile(UserSettingFile).exists())
     fileToLoad = UserSettingFile;
   else if (QFile(SystemSettingFile).exists())
     fileToLoad = SystemSettingFile;
   else
     fileToLoad = UserSettingFile;
-  m_settings = new QSettings(fileToLoad, QSettings::IniFormat);
-#endif
 
+  m_settings = new QSettings(fileToLoad, QSettings::IniFormat);
   m_settingsProxy = std::make_shared<QSettingsProxy>();
   m_settingsProxy->load(fileToLoad);
-  qInfo().noquote() << "settings file:" << m_settings->fileName();
+  qInfo().noquote() << "initial settings file:" << m_settings->fileName();
 }
 
 void Settings::cleanSettings()
@@ -143,7 +140,7 @@ QVariant Settings::defaultValue(const QString &key)
     return 4; // INFO
 
   if (key == Daemon::Elevate)
-    return Settings::isNativeMode();
+    return !Settings::isPortableMode();
 
   if (key == Core::UpdateUrl)
     return kUrlUpdateCheck;
@@ -155,10 +152,12 @@ QVariant Settings::defaultValue(const QString &key)
     return 24800;
 
   if (key == Core::ProcessMode) {
-    if (Settings::isNativeMode())
+#ifdef Q_OS_WIN
+    if (!Settings::isPortableMode())
       return Settings::ProcessMode::Service;
-    else
-      return Settings::ProcessMode::Desktop;
+#endif
+
+    return Settings::ProcessMode::Desktop;
   }
 
   if (key == Daemon::LogFile) {
@@ -196,14 +195,13 @@ QStringList Settings::validKeys()
 
 bool Settings::isWritable()
 {
-  if (Settings::isNativeMode())
-    return true;
   return instance()->m_settings->isWritable();
 }
 
-bool Settings::isNativeMode()
+bool Settings::isPortableMode()
 {
-  return instance()->m_settings->format() == QSettings::NativeFormat;
+  // Enable portable mode only if the portable settings file exists in the expected location.
+  return QFile(portableSettingsFile()).exists();
 }
 
 QString Settings::settingsFile()
@@ -213,8 +211,11 @@ QString Settings::settingsFile()
 
 QString Settings::settingsPath()
 {
-  if (instance()->isNativeMode())
+#ifdef Q_OS_WIN
+  if (!isPortableMode())
     return SystemDir;
+#endif
+
   return QFileInfo(instance()->m_settings->fileName()).absolutePath();
 }
 
@@ -263,3 +264,10 @@ void Settings::restoreDefaultSettings()
     instance()->setValue(key, defaultValue(key));
   }
 }
+
+QString Settings::portableSettingsFile()
+{
+  static const auto filename =
+      QStringLiteral("%1/settings/%2.conf").arg(QCoreApplication::applicationDirPath(), kAppName);
+  return filename;
+}
diff --git a/src/lib/common/Settings.h b/src/lib/common/Settings.h
index a67d1f43b..8e0973108 100644
--- a/src/lib/common/Settings.h
+++ b/src/lib/common/Settings.h
@@ -19,7 +19,7 @@ class Settings : public QObject
   Q_OBJECT
 public:
 #if defined(Q_OS_WIN)
-  inline const static auto UserDir = QStringLiteral("%1/AppData/Local/%2").arg(QDir::homePath(), kAppName);
+  inline const static auto UserDir = QStringLiteral("%1/AppData/Roaming/%2").arg(QDir::homePath(), kAppName);
   inline const static auto SystemDir = QStringLiteral("%1ProgramData/%2").arg(QDir::rootPath(), kAppName);
 #elif defined(Q_OS_MAC)
   inline const static auto UserDir = QStringLiteral("%1/Library/%2").arg(QDir::homePath(), kAppName);
@@ -28,6 +28,7 @@ public:
   inline const static auto UserDir = QStringLiteral("%1/.config/%2").arg(QDir::homePath(), kAppName);
   inline const static auto SystemDir = QStringLiteral("/etc/%1").arg(kAppName);
 #endif
+
   inline const static auto UserSettingFile = QStringLiteral("%1/%2.conf").arg(UserDir, kAppName);
   inline const static auto SystemSettingFile = QStringLiteral("%1/%2.conf").arg(SystemDir, kAppName);
 
@@ -120,7 +121,7 @@ public:
   static void restoreDefaultSettings();
   static QVariant defaultValue(const QString &key);
   static bool isWritable();
-  static bool isNativeMode();
+  static bool isPortableMode();
   static QString settingsFile();
   static QString settingsPath();
   static QString tlsDir();
@@ -132,6 +133,7 @@ public:
   static void save(bool emitSaving = true);
   static QStringList validKeys();
   static int logLevelToInt(const QString &level = "INFO");
+  static QString portableSettingsFile();
 
 Q_SIGNALS:
   void settingsChanged(const QString key);
@@ -145,7 +147,6 @@ private:
   void cleanSettings();
 
   QSettings *m_settings = nullptr;
-  QString m_portableSettingsFile = QStringLiteral("%1/settings/%2.conf");
   std::shared_ptr<QSettingsProxy> m_settingsProxy;
 
   // clang-format off
diff --git a/src/lib/gui/Diagnostic.cpp b/src/lib/gui/Diagnostic.cpp
index 25a4744fc..91559d273 100644
--- a/src/lib/gui/Diagnostic.cpp
+++ b/src/lib/gui/Diagnostic.cpp
@@ -44,7 +44,7 @@ void clearSettings(bool enableRestart)
   profileDir.removeRecursively();
 
 #ifdef Q_OS_WIN
-  if (!Settings::isNativeMode()) {
+  if (Settings::isPortableMode()) {
     // make a new empty portable settings file
     if (profileDir.mkpath(Settings::settingsPath())) {
       QFile file(Settings::settingsFile());
diff --git a/src/lib/gui/core/CoreProcess.cpp b/src/lib/gui/core/CoreProcess.cpp
index 336851fd3..d95c8cc57 100644
--- a/src/lib/gui/core/CoreProcess.cpp
+++ b/src/lib/gui/core/CoreProcess.cpp
@@ -349,6 +349,7 @@ void CoreProcess::start(std::optional<ProcessMode> processModeOption)
   if (processMode == ProcessMode::Desktop) {
     startForegroundProcess(args);
   } else if (processMode == ProcessMode::Service) {
+    args.append({QStringLiteral("--settings"), Settings::settingsFile()});
     startProcessFromDaemon(args);
   }
 
diff --git a/src/lib/gui/dialogs/SettingsDialog.cpp b/src/lib/gui/dialogs/SettingsDialog.cpp
index 66fcc92df..3efadad3a 100644
--- a/src/lib/gui/dialogs/SettingsDialog.cpp
+++ b/src/lib/gui/dialogs/SettingsDialog.cpp
@@ -271,8 +271,9 @@ void SettingsDialog::updateControls()
   ui->comboTlsKeyLength->setEnabled(writable);
   ui->cbCloseToTray->setEnabled(writable);
 
-  // Handle enable and disable of service items
-  if (Settings::isNativeMode()) {
+  // Portable mode only ever applies to Windows.
+  // Daemon options should only be available on Windows when *not* in portable mode.
+  if (!Settings::isPortableMode()) {
     ui->groupService->setEnabled(writable);
     ui->cbElevateDaemon->setEnabled(writable && serviceChecked);
   } else if (ui->groupService->isVisibleTo(ui->tabAdvanced)) {
diff --git a/src/unittests/common/SettingsTests.cpp b/src/unittests/common/SettingsTests.cpp
index 09b502f80..78540dc67 100644
--- a/src/unittests/common/SettingsTests.cpp
+++ b/src/unittests/common/SettingsTests.cpp
@@ -16,7 +16,7 @@ void SettingsTests::initTestCase()
     oldSettings.remove();
 }
 
-void SettingsTests::setSettingsFile()
+void SettingsTests::setSettingFile()
 {
   Settings::setSettingFile(m_settingsFile);
 }
diff --git a/src/unittests/common/SettingsTests.h b/src/unittests/common/SettingsTests.h
index d408504a6..70cd3c74a 100644
--- a/src/unittests/common/SettingsTests.h
+++ b/src/unittests/common/SettingsTests.h
@@ -14,7 +14,7 @@ class SettingsTests : public QObject
 private Q_SLOTS:
   void initTestCase();
   // Test are run in order top to bottom
-  void setSettingsFile();
+  void setSettingFile();
   void settingsFile();
   void settingsPath();
   void tlsDir();
@@ -24,9 +24,18 @@ private Q_SLOTS:
   void checkValidSettings();
 
 private:
-  inline static const QString m_settingsPath = QStringLiteral("tmp/test");
-  inline static const QString m_settingsFile = QStringLiteral("%1/Deskflow.conf").arg(m_settingsPath);
-  inline static const QString m_expectedTlsDir = QStringLiteral("tmp/test/%1").arg(kTlsDirName);
+  inline static const QString m_settingsPathTemp = QStringLiteral("tmp/test");
+  inline static const QString m_settingsFile = QStringLiteral("%1/Deskflow.conf").arg(m_settingsPathTemp);
+
+// Gotcha: On Windows non-portable mode, additional config files such as TLS config are saved
+// in 'Program Data' and are not stored in the same place as the settings file.
+#ifdef Q_OS_WIN
+  inline static const QString m_settingsPath = Settings::SystemDir;
+#else
+  inline static const QString m_settingsPath = m_settingsPathTemp;
+#endif
+
+  inline static const QString m_expectedTlsDir = QStringLiteral("%1/%2").arg(m_settingsPath, kTlsDirName);
   inline static const QString m_expectedTlsLocalDB =
       QStringLiteral("%1/%2").arg(m_expectedTlsDir, kTlsFingerprintLocalFilename);
   inline static const QString m_expectedTlsServerDB =