Index: lldb/packages/Python/lldbsuite/test/lldbtest.py
===================================================================
--- lldb/packages/Python/lldbsuite/test/lldbtest.py
+++ lldb/packages/Python/lldbsuite/test/lldbtest.py
@@ -1058,6 +1058,13 @@
         lldb.SBDebugger.Destroy(self.dbg)
         del self.dbg
 
+        # Modules are not orphaned during reproducer replay because they're
+        # leaked on purpose.
+        if not configuration.is_reproducer():
+            # Assert that the global module cache is empty.
+            self.assertEqual(lldb.SBModule.GetNumberAllocatedModules(), 0)
+
+
     # =========================================================
     # Various callbacks to allow introspection of test progress
     # =========================================================
@@ -2021,13 +2028,9 @@
         for target in targets:
             self.dbg.DeleteTarget(target)
 
-        # Modules are not orphaned during reproducer replay because they're
-        # leaked on purpose.
         if not configuration.is_reproducer():
             # Assert that all targets are deleted.
-            assert self.dbg.GetNumTargets() == 0
-            # Assert that the global module cache is empty.
-            assert lldb.SBModule.GetNumberAllocatedModules() == 0
+            self.assertEqual(self.dbg.GetNumTargets(), 0)
 
         # Do this last, to make sure it's in reverse order from how we setup.
         Base.tearDown(self)
Index: lldb/source/Core/Debugger.cpp
===================================================================
--- lldb/source/Core/Debugger.cpp
+++ lldb/source/Core/Debugger.cpp
@@ -600,10 +600,14 @@
     for (pos = g_debugger_list_ptr->begin(); pos != end; ++pos) {
       if ((*pos).get() == debugger_sp.get()) {
         g_debugger_list_ptr->erase(pos);
-        return;
+        break;
       }
     }
   }
+
+  // Clean any modules that are orphaned.
+  bool mandatory = true;
+  ModuleList::RemoveOrphanSharedModules(mandatory);
 }
 
 DebuggerSP Debugger::FindDebuggerWithInstanceName(ConstString instance_name) {