diff --git a/src/node/blockstorage.cpp b/src/node/blockstorage.cpp
index 78416ec5765..157acf10973 100644
--- a/src/node/blockstorage.cpp
+++ b/src/node/blockstorage.cpp
@@ -644,7 +644,7 @@ bool BlockManager::FindBlockPos(FlatFilePos& pos, unsigned int nAddSize, unsigne
             // when the undo file is keeping up with the block file, we want to flush it explicitly
             // when it is lagging behind (more blocks arrive than are being connected), we let the
             // undo block write case handle it
-            finalize_undo = (m_blockfile_info[nFile].nHeightLast == (unsigned int)active_chain.Tip()->nHeight);
+            finalize_undo = (m_blockfile_info[nFile].nHeightLast == m_undo_height_in_last_blockfile);
             nFile++;
             if (m_blockfile_info.size() <= nFile) {
                 m_blockfile_info.resize(nFile + 1);
@@ -660,6 +660,7 @@ bool BlockManager::FindBlockPos(FlatFilePos& pos, unsigned int nAddSize, unsigne
         }
         FlushBlockFile(!fKnown, finalize_undo);
         m_last_blockfile = nFile;
+        m_undo_height_in_last_blockfile = 0; // No undo data yet in the new file, so reset our undo-height tracking.
     }
 
     m_blockfile_info[nFile].AddBlock(nHeight, nTime);
@@ -749,8 +750,9 @@ bool BlockManager::WriteUndoDataForBlock(const CBlockUndo& blockundo, BlockValid
         // the FindBlockPos function
         if (_pos.nFile < m_last_blockfile && static_cast<uint32_t>(block.nHeight) == m_blockfile_info[_pos.nFile].nHeightLast) {
             FlushUndoFile(_pos.nFile, true);
+        } else if (_pos.nFile == m_last_blockfile && static_cast<uint32_t>(block.nHeight) > m_undo_height_in_last_blockfile) {
+            m_undo_height_in_last_blockfile = block.nHeight;
         }
-
         // update nUndoPos in block index
         block.nUndoPos = _pos.nPos;
         block.nStatus |= BLOCK_HAVE_UNDO;
diff --git a/src/node/blockstorage.h b/src/node/blockstorage.h
index c2e903e4701..1344fa04ded 100644
--- a/src/node/blockstorage.h
+++ b/src/node/blockstorage.h
@@ -128,6 +128,19 @@ private:
     RecursiveMutex cs_LastBlockFile;
     std::vector<CBlockFileInfo> m_blockfile_info;
     int m_last_blockfile = 0;
+
+    // Track the height of the highest block in m_last_blockfile whose undo
+    // data has been written. Block data is written to block files in download
+    // order, but is written to undo files in validation order, which is
+    // usually in order by height. To avoid wasting disk space, undo files will
+    // be trimmed whenever the corresponding block file is finalized and
+    // the height of the highest block written to the block file equals the
+    // height of the highest block written to the undo file. This is a
+    // heuristic and can sometimes preemptively trim undo files that will write
+    // more data later, and sometimes fail to trim undo files that can't have
+    // more data written later.
+    unsigned int m_undo_height_in_last_blockfile = 0;
+
     /** Global flag to indicate we should check to see if there are
      *  block/undo files that should be deleted.  Set on startup
      *  or if we allocate more file space when we're in prune mode