diff --git a/src/tiled/mainwindow.cpp b/src/tiled/mainwindow.cpp
index c8ec75f53c..8857fc0fbe 100644
--- a/src/tiled/mainwindow.cpp
+++ b/src/tiled/mainwindow.cpp
@@ -68,6 +68,7 @@
 #include "tilesetdocument.h"
 #include "tileseteditor.h"
 #include "tilesetmanager.h"
+#include "tilestampmanager.h"
 #include "tmxmapformat.h"
 #include "utils.h"
 #include "world.h"
@@ -1017,6 +1018,11 @@ void MainWindow::initializeSession()
     // adding the project's extension path.
     ScriptManager::instance().ensureInitialized();
 
+    // Load tile stamps (delayed so that potential custom types and file
+    // formats can be supported by stamps - which isn't perfect since there
+    // will still be issues when the project isn't open on startup)
+    TileStampManager::instance()->loadStamps();
+
     if (projectLoaded || Preferences::instance()->restoreSessionOnStartup())
         restoreSession();
 }
diff --git a/src/tiled/projectmanager.cpp b/src/tiled/projectmanager.cpp
index d7ff950be0..536e39faf3 100644
--- a/src/tiled/projectmanager.cpp
+++ b/src/tiled/projectmanager.cpp
@@ -37,6 +37,11 @@ ProjectManager::ProjectManager(QObject *parent)
     ourInstance = this;
 }
 
+ProjectManager::~ProjectManager()
+{
+    ourInstance = nullptr;
+}
+
 /**
  * Replaces the current project with the given \a project.
  */
diff --git a/src/tiled/projectmanager.h b/src/tiled/projectmanager.h
index 22d93d1239..19fef2d501 100644
--- a/src/tiled/projectmanager.h
+++ b/src/tiled/projectmanager.h
@@ -40,6 +40,7 @@ class TILED_EDITOR_EXPORT ProjectManager : public QObject
 
 public:
     explicit ProjectManager(QObject *parent = nullptr);
+    ~ProjectManager() override;
 
     static ProjectManager *instance();
 
diff --git a/src/tiled/tilestampmanager.cpp b/src/tiled/tilestampmanager.cpp
index 3fc63e25d7..764c52ff30 100644
--- a/src/tiled/tilestampmanager.cpp
+++ b/src/tiled/tilestampmanager.cpp
@@ -29,10 +29,6 @@
 #include "preferences.h"
 #include "savefile.h"
 #include "stampbrush.h"
-#include "tilelayer.h"
-#include "tileselectiontool.h"
-#include "tileset.h"
-#include "tilesetmanager.h"
 #include "tilestampmodel.h"
 #include "toolmanager.h"
 #include "utils.h"
@@ -46,6 +42,8 @@
 
 using namespace Tiled;
 
+TileStampManager *TileStampManager::ourInstance;
+
 TileStampManager::TileStampManager(const ToolManager &toolManager,
                                    QObject *parent)
     : QObject(parent)
@@ -54,6 +52,9 @@ TileStampManager::TileStampManager(const ToolManager &toolManager,
     , mTileStampModel(new TileStampModel(this))
     , mToolManager(toolManager)
 {
+    Q_ASSERT(!ourInstance);
+    ourInstance = this;
+
     mRegisteredCb = stampsDirectory.onChange([this] { stampsDirectoryChanged(); });
 
     connect(mTileStampModel, &TileStampModel::stampAdded,
@@ -64,8 +65,6 @@ TileStampManager::TileStampManager(const ToolManager &toolManager,
             this, &TileStampManager::saveStamp);
     connect(mTileStampModel, &TileStampModel::stampRemoved,
             this, &TileStampManager::deleteStamp);
-
-    loadStamps();
 }
 
 TileStampManager::~TileStampManager()
@@ -73,6 +72,8 @@ TileStampManager::~TileStampManager()
     // needs to be over here where the TileStamp type is complete
 
     stampsDirectory.unregister(mRegisteredCb);
+
+    ourInstance = nullptr;
 }
 
 static TileStamp stampFromContext(AbstractTool *selectedTool)
diff --git a/src/tiled/tilestampmanager.h b/src/tiled/tilestampmanager.h
index dc90f6d899..9f8a41c351 100644
--- a/src/tiled/tilestampmanager.h
+++ b/src/tiled/tilestampmanager.h
@@ -51,12 +51,16 @@ class TileStampManager : public QObject
     TileStampManager(const ToolManager &toolManager, QObject *parent = nullptr);
     ~TileStampManager() override;
 
+    static TileStampManager *instance();
+
     static QList<Qt::Key> quickStampKeys();
 
     TileStampModel *tileStampModel() const;
 
     SessionOption<QString> stampsDirectory;
 
+    void loadStamps();
+
 public slots:
     TileStamp createStamp();
     void addVariation(const TileStamp &targetStamp);
@@ -76,8 +80,6 @@ public slots:
     void eraseQuickStamp(int index);
     void setQuickStamp(int index, TileStamp stamp);
 
-    void loadStamps();
-
 private:
     void stampAdded(TileStamp stamp);
     void stampRenamed(TileStamp stamp);
@@ -93,9 +95,16 @@ public slots:
     Session::CallbackIterator mRegisteredCb;
 
     const ToolManager &mToolManager;
+
+    static TileStampManager *ourInstance;
 };
 
 
+inline TileStampManager *TileStampManager::instance()
+{
+    return ourInstance;
+}
+
 /**
  * Returns the keys used for quickly accessible tile stamps.
  * Note: To store a tile layer <Ctrl> is added. The given keys will work