diff --git a/qrenderdoc/Windows/Dialogs/ExtensionManager.cpp b/qrenderdoc/Windows/Dialogs/ExtensionManager.cpp
index dd1d71535..128d9be0e 100644
--- a/qrenderdoc/Windows/Dialogs/ExtensionManager.cpp
+++ b/qrenderdoc/Windows/Dialogs/ExtensionManager.cpp
@@ -298,7 +298,11 @@ void ExtensionManager::update_currentItem(RDTreeWidgetItem *item)
       ui->reload->setEnabled(true);
       ui->reload->setText(loaded ? tr("Reload") : tr("Load"));
       ui->output->setEnabled(loaded);
-      ui->debug->setEnabled(loaded);
+      ui->debug->setEnabled(loaded && PythonContext::IsDebuggingEnabled());
+      ui->debug->setToolTip(QString());
+      if(loaded && !PythonContext::IsDebuggingEnabled())
+        ui->debug->setToolTip(
+            tr("Debugging not supported - check documentation for setup instructions"));
       ui->alwaysLoad->setEnabled(loaded);
 
       ui->alwaysLoad->setChecked(m_Ctx.Config().AlwaysLoad_Extensions.contains(e.package));
diff --git a/qrenderdoc/Windows/PythonShell.cpp b/qrenderdoc/Windows/PythonShell.cpp
index be510fa0c..c3d8ba0cb 100644
--- a/qrenderdoc/Windows/PythonShell.cpp
+++ b/qrenderdoc/Windows/PythonShell.cpp
@@ -27,6 +27,7 @@
 #include <QKeyEvent>
 #include <QMenu>
 #include <QScrollBar>
+#include <QTimer>
 #include "Code/QRDUtils.h"
 #include "Code/ScintillaSyntax.h"
 #include "Code/pyrenderdoc/PythonContext.h"
@@ -1086,6 +1087,16 @@ PythonShell::PythonShell(ICaptureContext &ctx, QWidget *parent)
   // reset output to default
   on_clear_clicked();
   on_newScript_clicked();
+
+  // we defer debugging loading onto a thread so check after a delay
+  QTimer::singleShot(1200, [this]() {
+    if(!PythonContext::IsDebuggingEnabled())
+    {
+      ui->debugScript->setEnabled(false);
+      ui->debugScript->setToolTip(
+          tr("Debugging not supported - check documentation for setup instructions"));
+    }
+  });
 }
 
 PythonShell::~PythonShell()