diff --git a/lldb/include/lldb/Target/ThreadPlan.h b/lldb/include/lldb/Target/ThreadPlan.h
--- a/lldb/include/lldb/Target/ThreadPlan.h
+++ b/lldb/include/lldb/Target/ThreadPlan.h
@@ -351,6 +351,12 @@
 
   virtual bool ShouldStop(Event *event_ptr) = 0;
 
+  /// Returns whether this thread plan overrides the `ShouldStop` of previous
+  /// plans.
+  ///
+  /// When processing the thread plan stack, this function gives plans the
+  /// ability to continue - even when previous plans subsequently return false
+  /// from `ShouldStop`. \see Thread::ShouldStop
   virtual bool ShouldAutoContinue(Event *event_ptr) { return false; }
 
   // Whether a "stop class" event should be reported to the "outside world".
diff --git a/lldb/source/Target/Thread.cpp b/lldb/source/Target/Thread.cpp
--- a/lldb/source/Target/Thread.cpp
+++ b/lldb/source/Target/Thread.cpp
@@ -829,6 +829,8 @@
       ThreadPlan *plan_ptr = current_plan;
       while ((plan_ptr = GetPreviousPlan(plan_ptr)) != nullptr) {
         if (plan_ptr->PlanExplainsStop(event_ptr)) {
+          LLDB_LOGF(log, "Plan %s explains stop.", plan_ptr->GetName());
+
           should_stop = plan_ptr->ShouldStop(event_ptr);
 
           // plan_ptr explains the stop, next check whether plan_ptr is done,
@@ -858,10 +860,7 @@
   }
 
   if (!done_processing_current_plan) {
-    bool over_ride_stop = current_plan->ShouldAutoContinue(event_ptr);
-
-    LLDB_LOGF(log, "Plan %s explains stop, auto-continue %i.",
-              current_plan->GetName(), over_ride_stop);
+    bool override_stop = false;
 
     // We're starting from the base plan, so just let it decide;
     if (current_plan->IsBasePlan()) {
@@ -882,19 +881,24 @@
           if (should_stop)
             current_plan->WillStop();
 
+          PopPlan();
+
+          if (current_plan->ShouldAutoContinue(event_ptr)) {
+            override_stop = true;
+            LLDB_LOGF(log, "Plan %s auto-continue: true.",
+                      current_plan->GetName());
+          }
+
           // If a Master Plan wants to stop, we let it. Otherwise, see if the
           // plan's parent wants to stop.
 
           if (should_stop && current_plan->IsMasterPlan()) {
-            PopPlan();
             break;
-          } else {
-            PopPlan();
+          }
 
-            current_plan = GetCurrentPlan();
-            if (current_plan == nullptr) {
-              break;
-            }
+          current_plan = GetCurrentPlan();
+          if (current_plan == nullptr) {
+            break;
           }
         } else {
           break;
@@ -902,7 +906,7 @@
       }
     }
 
-    if (over_ride_stop)
+    if (override_stop)
       should_stop = false;
   }