diff --git a/include/sta/BoundedHeap.hh b/include/sta/BoundedHeap.hh
index af934e0c..676c1e39 100644
--- a/include/sta/BoundedHeap.hh
+++ b/include/sta/BoundedHeap.hh
@@ -27,6 +27,7 @@
 #include <vector>
 #include <algorithm>
 #include <functional>
+#include <optional>
 
 namespace sta {
 
@@ -118,13 +119,14 @@ public:
   // If the heap is not full, the element is added.
   // If the heap is full and the new element is better than the worst element,
   // the worst element is replaced. Otherwise, the element is ignored.
-  // Returns true if the element was inserted, false if it was ignored.
-  bool
+  // Returns (inserted, displaced): inserted is true if the element was inserted,
+  // displaced is set when an element was pushed out (caller must handle ownership).
+  std::pair<bool, std::optional<T>>
   insert(const T& value) {
     if (heap_.size() < max_size_) {
       heap_.push_back(value);
       std::push_heap(heap_.begin(), heap_.end(), min_heap_comp_);
-      return true;
+      return {true, std::nullopt};
     }
     else if (!heap_.empty()) {
       // When keeping N worst (smallest) values: if new value is smaller than worst,
@@ -134,23 +136,25 @@ public:
       if (comp_(value, heap_.front())) {
         // New value is smaller than worst - find and replace the largest element
         auto max_it = std::max_element(heap_.begin(), heap_.end(), comp_);
+        T displaced = std::move(*max_it);
         *max_it = value;
         // Rebuild heap since we modified an internal element
         std::make_heap(heap_.begin(), heap_.end(), min_heap_comp_);
-        return true;
+        return {true, std::move(displaced)};
       }
       // Otherwise, new value is >= worst, so we already have worse values - reject it
     }
-    return false;
+    return {false, std::nullopt};
   }
 
   // Insert an element using move semantics
-  bool insert(T&& value)
+  std::pair<bool, std::optional<T>>
+  insert(T&& value)
   {
     if (heap_.size() < max_size_) {
       heap_.push_back(std::move(value));
       std::push_heap(heap_.begin(), heap_.end(), min_heap_comp_);
-      return true;
+      return {true, std::nullopt};
     }
     else if (!heap_.empty()) {
       // When keeping N worst (smallest) values: if new value is smaller than worst,
@@ -160,14 +164,15 @@ public:
       if (comp_(value, heap_.front())) {
         // New value is smaller than worst - find and replace the largest element
         auto max_it = std::max_element(heap_.begin(), heap_.end(), comp_);
+        T displaced = std::move(*max_it);
         *max_it = std::move(value);
         // Rebuild heap since we modified an internal element
         std::make_heap(heap_.begin(), heap_.end(), min_heap_comp_);
-        return true;
+        return {true, std::move(displaced)};
       }
       // Otherwise, new value is >= worst, so we already have worse values - reject it
     }
-    return false;
+    return {false, std::nullopt};
   }
 
   // Extract all elements sorted from best to worst.
diff --git a/include/sta/PathGroup.hh b/include/sta/PathGroup.hh
index 03bcb0c5..f71b9f38 100644
--- a/include/sta/PathGroup.hh
+++ b/include/sta/PathGroup.hh
@@ -67,6 +67,7 @@ public:
                                        float min_slack,
                                        float max_slack,
                                        const StaState *sta);
+  ~PathGroup();
   const std::string &name() const { return name_; }
   const MinMax *minMax() const { return min_max_;}
   PathEndSeq pathEnds() const;
diff --git a/search/PathGroup.cc b/search/PathGroup.cc
index 1fb9e4ea..7a5ccd33 100644
--- a/search/PathGroup.cc
+++ b/search/PathGroup.cc
@@ -105,6 +105,12 @@ PathGroup::PathGroup(const char *name,
 {
 }
 
+PathGroup::~PathGroup()
+{
+  PathEndSeq path_ends = heap_.extract();
+  deleteContents(path_ends);
+}
+
 PathEndSeq
 PathGroup::pathEnds() const
 {
@@ -170,15 +176,20 @@ void
 PathGroup::insert(PathEnd *path_end)
 {
   LockGuard lock(lock_);
-  heap_.insert(path_end);
-  path_end->setPathGroup(this);
+  auto [inserted, displaced] = heap_.insert(path_end);
+  if (inserted)
+    path_end->setPathGroup(this);
+  else
+    delete path_end;
+  if (displaced)
+    delete *displaced;
 }
 
 void
 PathGroup::pushEnds(PathEndSeq &path_ends)
 {
   if (!heap_.empty()) {
-    PathEndSeq ends = heap_.extract();
+    PathEndSeq ends = heap_.contents();
     path_ends.reserve(path_ends.size() + ends.size());
     // Append heap path ends to path_ends.
     path_ends.insert(path_ends.end(),