diff --git a/src/core/ConfigManager.cpp b/src/core/ConfigManager.cpp
index 734ccb80e46..a99223a9d41 100644
--- a/src/core/ConfigManager.cpp
+++ b/src/core/ConfigManager.cpp
@@ -225,9 +225,9 @@ bool ConfigManager::hasWorkingDir() const
 }
 
 
-void ConfigManager::setWorkingDir( const QString & _wd )
+void ConfigManager::setWorkingDir( const QString & wd )
 {
-	m_workingDir = ensureTrailingSlash( _wd );
+	m_workingDir = ensureTrailingSlash( QFileInfo( wd ).canonicalFilePath() );
 }
 
 
diff --git a/src/core/SampleBuffer.cpp b/src/core/SampleBuffer.cpp
index cb930b08789..141085dd2d9 100644
--- a/src/core/SampleBuffer.cpp
+++ b/src/core/SampleBuffer.cpp
@@ -1415,7 +1415,8 @@ QString SampleBuffer::tryToMakeRelative( const QString & file )
 {
 	if( QFileInfo( file ).isRelative() == false )
 	{
-		QString f = QString( file ).replace( QDir::separator(), '/' );
+		// Normalize the path
+		QString f = QFileInfo( file ).canonicalFilePath().replace( QDir::separator(), '/' );
 
 		// First, look in factory samples
 		// Isolate "samples/" from "data:/samples/"
diff --git a/tests/src/core/RelativePathsTest.cpp b/tests/src/core/RelativePathsTest.cpp
index 555fa39b56a..6a75483776a 100644
--- a/tests/src/core/RelativePathsTest.cpp
+++ b/tests/src/core/RelativePathsTest.cpp
@@ -40,8 +40,11 @@ private slots:
 
 		QString absPath = fi.absoluteFilePath();
 		QString relPath = "drums/kick01.ogg";
+		QString fuzPath = absPath;
+		fuzPath.replace(relPath, "drums/.///kick01.ogg");
 		QCOMPARE(SampleBuffer::tryToMakeRelative(absPath), relPath);
 		QCOMPARE(SampleBuffer::tryToMakeAbsolute(relPath), absPath);
+		QCOMPARE(SampleBuffer::tryToMakeRelative(fuzPath), relPath);
 	}
 } RelativePathTests;