diff --git a/src/libs/utils/pathchooser.cpp b/src/libs/utils/pathchooser.cpp
index 42889793958..1de09370e06 100644
--- a/src/libs/utils/pathchooser.cpp
+++ b/src/libs/utils/pathchooser.cpp
@@ -322,7 +322,12 @@ QString PathChooser::path() const
 
 QString PathChooser::rawPath() const
 {
-    return FileName::fromUserInput(QDir::fromNativeSeparators(d->m_lineEdit->text())).toString();
+    return rawFileName().toString();
+}
+
+FileName PathChooser::rawFileName() const
+{
+    return FileName::fromUserInput(d->m_lineEdit->text());
 }
 
 FileName PathChooser::fileName() const
diff --git a/src/libs/utils/pathchooser.h b/src/libs/utils/pathchooser.h
index 10f01ad162a..b71f38841ce 100644
--- a/src/libs/utils/pathchooser.h
+++ b/src/libs/utils/pathchooser.h
@@ -98,6 +98,7 @@ public:
 
     QString path() const;
     QString rawPath() const; // The raw unexpanded input.
+    FileName rawFileName() const; // The raw unexpanded input.
     FileName fileName() const;
 
     QString baseDirectory() const;
diff --git a/src/plugins/projectexplorer/runconfigurationaspects.cpp b/src/plugins/projectexplorer/runconfigurationaspects.cpp
index 203420ce306..d545a859ccb 100644
--- a/src/plugins/projectexplorer/runconfigurationaspects.cpp
+++ b/src/plugins/projectexplorer/runconfigurationaspects.cpp
@@ -162,10 +162,10 @@ void WorkingDirectoryAspect::addToMainConfigurationWidget(QWidget *parent, QForm
     m_chooser->setHistoryCompleter(m_key);
     m_chooser->setExpectedKind(Utils::PathChooser::Directory);
     m_chooser->setPromptDialogTitle(tr("Select Working Directory"));
-    m_chooser->lineEdit()->setPlaceholderText(m_defaultWorkingDirectory);
-    m_chooser->setPath(m_workingDirectory);
+    m_chooser->lineEdit()->setPlaceholderText(m_defaultWorkingDirectory.toUserOutput());
+    m_chooser->setFileName(m_workingDirectory);
     connect(m_chooser.data(), &PathChooser::pathChanged, this,
-            [this]() { m_workingDirectory = m_chooser->rawPath(); });
+            [this]() { m_workingDirectory = m_chooser->rawFileName(); });
 
     auto resetButton = new QToolButton(parent);
     resetButton->setToolTip(tr("Reset to Default"));
@@ -197,39 +197,40 @@ void WorkingDirectoryAspect::resetPath()
 
 void WorkingDirectoryAspect::fromMap(const QVariantMap &map)
 {
-    m_workingDirectory = map.value(m_key).toString();
-    m_defaultWorkingDirectory = map.value(keyForDefaultWd()).toString();
+    m_workingDirectory = FileName::fromString(map.value(m_key).toString());
+    m_defaultWorkingDirectory = FileName::fromString(map.value(keyForDefaultWd()).toString());
 }
 
 void WorkingDirectoryAspect::toMap(QVariantMap &data) const
 {
-    data.insert(m_key, m_workingDirectory);
-    data.insert(keyForDefaultWd(), m_defaultWorkingDirectory);
+    data.insert(m_key, m_workingDirectory.toString());
+    data.insert(keyForDefaultWd(), m_defaultWorkingDirectory.toString());
 }
 
-QString WorkingDirectoryAspect::workingDirectory() const
+FileName WorkingDirectoryAspect::workingDirectory() const
 {
     QTC_ASSERT(m_chooser, return m_defaultWorkingDirectory);
-    return m_workingDirectory.isEmpty()
-            ? m_defaultWorkingDirectory
-            : runConfiguration()->macroExpander()->expandProcessArgs(m_chooser->path());
+    if (m_workingDirectory.isEmpty())
+        return m_defaultWorkingDirectory;
+    return FileName::fromString(
+                runConfiguration()->macroExpander()->expandProcessArgs(m_chooser->path()));
 }
 
-QString WorkingDirectoryAspect::defaultWorkingDirectory() const
+FileName WorkingDirectoryAspect::defaultWorkingDirectory() const
 {
     return m_defaultWorkingDirectory;
 }
 
-QString WorkingDirectoryAspect::unexpandedWorkingDirectory() const
+FileName WorkingDirectoryAspect::unexpandedWorkingDirectory() const
 {
     return m_workingDirectory;
 }
 
-void WorkingDirectoryAspect::setDefaultWorkingDirectory(const QString &defaultWorkingDir)
+void WorkingDirectoryAspect::setDefaultWorkingDirectory(const FileName &defaultWorkingDir)
 {
     m_defaultWorkingDirectory = defaultWorkingDir;
     if (m_chooser)
-        m_chooser->lineEdit()->setPlaceholderText(m_defaultWorkingDirectory);
+        m_chooser->lineEdit()->setPlaceholderText(m_defaultWorkingDirectory.toUserOutput());
 }
 
 PathChooser *WorkingDirectoryAspect::pathChooser() const
diff --git a/src/plugins/projectexplorer/runconfigurationaspects.h b/src/plugins/projectexplorer/runconfigurationaspects.h
index aa9fb94edc5..b1794c72303 100644
--- a/src/plugins/projectexplorer/runconfigurationaspects.h
+++ b/src/plugins/projectexplorer/runconfigurationaspects.h
@@ -34,6 +34,8 @@
 #include "runconfiguration.h"
 #include "applicationlauncher.h"
 
+#include <utils/fileutils.h>
+
 QT_BEGIN_NAMESPACE
 class QCheckBox;
 class QFormLayout;
@@ -92,10 +94,10 @@ public:
 
     void addToMainConfigurationWidget(QWidget *parent, QFormLayout *layout);
 
-    QString workingDirectory() const;
-    QString defaultWorkingDirectory() const;
-    QString unexpandedWorkingDirectory() const;
-    void setDefaultWorkingDirectory(const QString &defaultWorkingDir);
+    Utils::FileName workingDirectory() const;
+    Utils::FileName defaultWorkingDirectory() const;
+    Utils::FileName unexpandedWorkingDirectory() const;
+    void setDefaultWorkingDirectory(const Utils::FileName &defaultWorkingDir);
     Utils::PathChooser *pathChooser() const;
 
 private:
@@ -105,8 +107,8 @@ private:
     void resetPath();
     QString keyForDefaultWd() const;
 
-    QString m_workingDirectory;
-    QString m_defaultWorkingDirectory;
+    Utils::FileName m_workingDirectory;
+    Utils::FileName m_defaultWorkingDirectory;
     QPointer<Utils::PathChooser> m_chooser;
     QString m_key;
 };
diff --git a/src/plugins/qbsprojectmanager/qbsrunconfiguration.cpp b/src/plugins/qbsprojectmanager/qbsrunconfiguration.cpp
index 286d960ca7c..20cd94feea3 100644
--- a/src/plugins/qbsprojectmanager/qbsrunconfiguration.cpp
+++ b/src/plugins/qbsprojectmanager/qbsrunconfiguration.cpp
@@ -248,7 +248,7 @@ QString QbsRunConfiguration::workingDirectory() const
 {
     const auto *wdAspect = extraAspect<WorkingDirectoryAspect>();
     QTC_ASSERT(wdAspect, return baseWorkingDirectory());
-    return wdAspect->workingDirectory();
+    return wdAspect->workingDirectory().toString();
 }
 
 QString QbsRunConfiguration::baseWorkingDirectory() const
@@ -393,7 +393,7 @@ void QbsRunConfigurationWidget::targetInformationHasChanged()
     setExecutableLineText(m_rc->executable());
 
     WorkingDirectoryAspect *aspect = m_rc->extraAspect<WorkingDirectoryAspect>();
-    aspect->setDefaultWorkingDirectory(m_rc->baseWorkingDirectory());
+    aspect->setDefaultWorkingDirectory(Utils::FileName::fromString(m_rc->baseWorkingDirectory()));
     aspect->pathChooser()->setBaseFileName(m_rc->target()->project()->projectDirectory());
     m_ignoreChange = false;
 }
diff --git a/src/plugins/qmakeprojectmanager/desktopqmakerunconfiguration.cpp b/src/plugins/qmakeprojectmanager/desktopqmakerunconfiguration.cpp
index 6215b4189ed..3523f31da17 100644
--- a/src/plugins/qmakeprojectmanager/desktopqmakerunconfiguration.cpp
+++ b/src/plugins/qmakeprojectmanager/desktopqmakerunconfiguration.cpp
@@ -316,7 +316,7 @@ void DesktopQmakeRunConfigurationWidget::effectiveTargetInformationChanged()
 
     m_ignoreChange = true;
     auto aspect = m_qmakeRunConfiguration->extraAspect<WorkingDirectoryAspect>();
-    aspect->setDefaultWorkingDirectory(m_qmakeRunConfiguration->baseWorkingDirectory());
+    aspect->setDefaultWorkingDirectory(FileName::fromString(m_qmakeRunConfiguration->baseWorkingDirectory()));
     aspect->pathChooser()->setBaseFileName(m_qmakeRunConfiguration->target()->project()->projectDirectory());
     m_ignoreChange = false;
 }
@@ -393,7 +393,7 @@ void DesktopQmakeRunConfiguration::setUsingLibrarySearchPath(bool state)
 
 QString DesktopQmakeRunConfiguration::workingDirectory() const
 {
-    return extraAspect<WorkingDirectoryAspect>()->workingDirectory();
+    return extraAspect<WorkingDirectoryAspect>()->workingDirectory().toString();
 }
 
 QString DesktopQmakeRunConfiguration::baseWorkingDirectory() const