diff --git a/qrenderdoc/Code/CaptureContext.cpp b/qrenderdoc/Code/CaptureContext.cpp
index 7c80af76d..2b9fb4e33 100644
--- a/qrenderdoc/Code/CaptureContext.cpp
+++ b/qrenderdoc/Code/CaptureContext.cpp
@@ -422,6 +422,7 @@ rdcarray<ExtensionMetadata> CaptureContext::GetInstalledExtensions()
           ext.filePath = fileinfo.absolutePath();
 
           ext.hasChanges = m_DirtyExtensions.contains(rdcstr(package));
+          ext.failedLoad = m_FailedExtensions.contains(rdcstr(package));
 
           ext.extensionAPI = 1;
           if(json.contains(lit("extension_api")))
@@ -563,6 +564,7 @@ rdcstr CaptureContext::LoadExtension(rdcstr name)
       m_ExtensionObjects[name].swap(m_PendingExtensionObjects);
 
       m_DirtyExtensions.removeOne(name);
+      m_FailedExtensions.removeOne(name);
 
       for(const ExtensionMetadata &e : GetInstalledExtensions())
         if(e.package == name)
@@ -571,6 +573,7 @@ rdcstr CaptureContext::LoadExtension(rdcstr name)
     else
     {
       m_ExtensionObjects.remove(name);
+      m_FailedExtensions.push_back(name);
 
       for(QObject *o : m_PendingExtensionObjects)
         delete o;
diff --git a/qrenderdoc/Code/CaptureContext.h b/qrenderdoc/Code/CaptureContext.h
index d6420a2e7..ca00d4547 100644
--- a/qrenderdoc/Code/CaptureContext.h
+++ b/qrenderdoc/Code/CaptureContext.h
@@ -435,6 +435,7 @@ private:
   QList<QObject *> m_PendingExtensionObjects;
   QMap<rdcstr, QList<QObject *>> m_ExtensionObjects;
   rdcarray<rdcstr> m_DirtyExtensions;
+  rdcarray<rdcstr> m_FailedExtensions;
 
   QList<QPointer<RegisteredMenuItem>> m_RegisteredMenuItems;
 
diff --git a/qrenderdoc/Code/Interface/Extensions.h b/qrenderdoc/Code/Interface/Extensions.h
index 7c583c603..85452db7b 100644
--- a/qrenderdoc/Code/Interface/Extensions.h
+++ b/qrenderdoc/Code/Interface/Extensions.h
@@ -370,6 +370,14 @@ This will always be false if the extension is unloaded.
 :type: bool
 )");
   bool hasChanges = false;
+
+  DOCUMENT(R"(A flag indicating that the extension failed to load properly.
+
+This will always be false if the extension is unloaded.
+
+:type: bool
+)");
+  bool failedLoad = false;
 };
 
 DECLARE_REFLECTION_STRUCT(ExtensionMetadata);
diff --git a/qrenderdoc/Code/pyrenderdoc/PythonContext.cpp b/qrenderdoc/Code/pyrenderdoc/PythonContext.cpp
index 935b0b3b4..75fc7fff8 100644
--- a/qrenderdoc/Code/pyrenderdoc/PythonContext.cpp
+++ b/qrenderdoc/Code/pyrenderdoc/PythonContext.cpp
@@ -1423,9 +1423,10 @@ QString PythonContext::LoadExtension(ICaptureContext &ctx, const rdcstr &extensi
 
     if(!valueStr.isEmpty())
     {
-      qCritical("Error importing extension module. %s: %s", typeStr.toUtf8().data(),
-                valueStr.toUtf8().data());
-      ret += tr("Error importing extension module. %1: %2\n\n").arg(typeStr).arg(valueStr);
+      qCritical("Error importing extension module '%s'. %s: %s", extension.c_str(),
+                typeStr.toUtf8().data(), valueStr.toUtf8().data());
+      ret +=
+          tr("Error importing extension module '%1'. %2: %3\n\n").arg(extension).arg(typeStr).arg(valueStr);
 
       if(!frames.isEmpty())
       {
@@ -1443,7 +1444,7 @@ QString PythonContext::LoadExtension(ICaptureContext &ctx, const rdcstr &extensi
       }
     }
 
-    if(!ret.isEmpty() && reload)
+    if(!ret.isEmpty())
       m_ExtensionContext->addText(extension, true, ret);
   }
 
diff --git a/qrenderdoc/Windows/MainWindow.cpp b/qrenderdoc/Windows/MainWindow.cpp
index 7af7c2544..2bad07c72 100644
--- a/qrenderdoc/Windows/MainWindow.cpp
+++ b/qrenderdoc/Windows/MainWindow.cpp
@@ -248,7 +248,7 @@ MainWindow::MainWindow(ICaptureContext &ctx) : QMainWindow(NULL), ui(new Ui::Mai
   QObject::connect(extensionReload, &RDToolButton::clicked, [this]() {
     rdcarray<ExtensionMetadata> exts = m_Ctx.Extensions().GetInstalledExtensions();
     for(const ExtensionMetadata &m : exts)
-      if(m.hasChanges)
+      if(m.hasChanges || m.failedLoad)
         m_Ctx.Extensions().LoadExtension(m.package);
   });
   QObject::connect(PythonContext::GetExtensionContext(), &PythonContext::extensionLoaded, this,
@@ -1358,6 +1358,15 @@ void MainWindow::PythonStatusUpdate()
         break;
       }
     }
+    for(const ExtensionMetadata &m : m_Ctx.Extensions().GetInstalledExtensions())
+    {
+      if(m.failedLoad)
+      {
+        text += tr(" (some failed to load)");
+        reloadVisible = true;
+        break;
+      }
+    }
     extensionReload->setVisible(reloadVisible);
 
     if(PythonContext::IsDebuggerConnected())
diff --git a/qrenderdoc/Windows/PythonShell.cpp b/qrenderdoc/Windows/PythonShell.cpp
index d5d0a54ae..bc34f9af6 100644
--- a/qrenderdoc/Windows/PythonShell.cpp
+++ b/qrenderdoc/Windows/PythonShell.cpp
@@ -476,6 +476,11 @@ PythonShell::PythonShell(ICaptureContext &ctx, QWidget *parent)
   updateRecentFiles(false);
   updateExtensionProjects();
 
+  // on first launch we could be creating the python shell before extensions are loaded while
+  // initialising the UI. Refresh the extension projects after a short delay to pick up any
+  // additional information on loading status.
+  QTimer::singleShot(200, [this]() { updateExtensionProjects(); });
+
   ui->projectExplorer->endUpdate();
 
   ui->projectExplorer->expandItem(m_RecentFiles);
@@ -729,12 +734,18 @@ void PythonShell::updateExtensionProjects()
     if(ext.hasChanges)
       name += tr(" (Reload required)");
 
+    if(ext.failedLoad)
+      name += tr(" (Failed to load)");
+
     RDTreeWidgetItem *root = new RDTreeWidgetItem({name});
     root->setData(0, Qt::UserRole + 1, ext.package);
 
     if(ext.hasChanges)
       root->setItalic(true);
 
+    if(m_Ctx.Config().AlwaysLoad_Extensions.contains(ext.package))
+      root->setBold(true);
+
     addExtensionDirItems(root, QDir(ext.filePath));
 
     m_UIExtensions->addChild(root);
@@ -1949,7 +1960,7 @@ void PythonShell::projectExplorer_contextMenu(const QPoint &pos)
       {
         if(m.package == rdcstr(itemPath))
         {
-          reloadExtension.setEnabled(m.hasChanges);
+          reloadExtension.setEnabled(m.hasChanges || m.failedLoad);
           diskLocation = QFileInfo(m.filePath).absoluteFilePath();
           break;
         }