diff --git a/HISTORY.md b/HISTORY.md
index 7d622caa99..2055e6d743 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -17,6 +17,9 @@
 * RocksDB calls FileSystem::Poll API during FilePrefetchBuffer destruction which impacts performance as it waits for read requets completion which is not needed anymore. Calling FileSystem::AbortIO to abort those requests instead fixes that performance issue.
 * Fixed unnecessary block cache contention when queries within a MultiGet batch and across parallel batches access the same data block, which previously could cause severely degraded performance in this unusual case. (In more typical MultiGet cases, this fix is expected to yield a small or negligible performance improvement.)
 
+### Behavior changes
+* Enforce the existing contract of SingleDelete so that SingleDelete cannot be mixed with Delete because it leads to undefined behavior. Fix a number of unit tests that violate the contract but happen to pass.
+
 ## 7.2.0 (04/15/2022)
 ### Bug Fixes
 * Fixed bug which caused rocksdb failure in the situation when rocksdb was accessible using UNC path
diff --git a/db/compaction/compaction_iterator.cc b/db/compaction/compaction_iterator.cc
index a9e1990b8e..9f5bc4bc80 100644
--- a/db/compaction/compaction_iterator.cc
+++ b/db/compaction/compaction_iterator.cc
@@ -625,24 +625,34 @@ void CompactionIterator::NextFromInput() {
 
           TEST_SYNC_POINT_CALLBACK(
               "CompactionIterator::NextFromInput:SingleDelete:2", nullptr);
-          if (next_ikey.type == kTypeSingleDeletion ||
-              next_ikey.type == kTypeDeletion) {
+          if (next_ikey.type == kTypeSingleDeletion) {
             // We encountered two SingleDeletes for same key in a row. This
             // could be due to unexpected user input. If write-(un)prepared
             // transaction is used, this could also be due to releasing an old
             // snapshot between a Put and its matching SingleDelete.
-            // Furthermore, if write-(un)prepared transaction is rolled back
-            // after prepare, we will write a Delete to cancel a prior Put. If
-            // old snapshot is released between a later Put and its matching
-            // SingleDelete, we will end up with a Delete followed by
-            // SingleDelete.
             // Skip the first SingleDelete and let the next iteration decide
-            // how to handle the second SingleDelete or Delete.
+            // how to handle the second SingleDelete.
 
             // First SingleDelete has been skipped since we already called
             // input_.Next().
             ++iter_stats_.num_record_drop_obsolete;
             ++iter_stats_.num_single_del_mismatch;
+          } else if (next_ikey.type == kTypeDeletion) {
+            std::ostringstream oss;
+            oss << "Found SD and type: " << static_cast<int>(next_ikey.type)
+                << " on the same key, violating the contract "
+                   "of SingleDelete. Check your application to make sure the "
+                   "application does not mix SingleDelete and Delete for "
+                   "the same key. If you are using "
+                   "write-prepared/write-unprepared transactions, and use "
+                   "SingleDelete to delete certain keys, then make sure "
+                   "TransactionDBOptions::rollback_deletion_type_callback is "
+                   "configured properly. Mixing SD and DEL can lead to "
+                   "undefined behaviors";
+            ROCKS_LOG_ERROR(info_log_, "%s", oss.str().c_str());
+            valid_ = false;
+            status_ = Status::Corruption(oss.str());
+            return;
           } else if (!is_timestamp_eligible_for_gc) {
             // We cannot drop the SingleDelete as timestamp is enabled, and
             // timestamp of this key is greater than or equal to
diff --git a/db/compaction/compaction_job_test.cc b/db/compaction/compaction_job_test.cc
index 7d25646955..2032af44ab 100644
--- a/db/compaction/compaction_job_test.cc
+++ b/db/compaction/compaction_job_test.cc
@@ -890,10 +890,10 @@ TEST_F(CompactionJobTest, MultiSingleDelete) {
   //      -> Snapshot Put
   // K: SDel SDel Put SDel Put Put Snapshot SDel Put SDel SDel Put SDel
   //      -> Snapshot Put Snapshot SDel
-  // L: SDel Put Del Put SDel Snapshot Del Put Del SDel Put SDel
-  //      -> Snapshot SDel
-  // M: (Put) SDel Put Del Put SDel Snapshot Put Del SDel Put SDel Del
-  //      -> SDel Snapshot Del
+  // L: SDel Put SDel Put SDel Snapshot SDel Put SDel SDel Put SDel
+  //      -> Snapshot SDel Put SDel
+  // M: (Put) SDel Put SDel Put SDel Snapshot Put SDel SDel Put SDel SDel
+  //      -> SDel Snapshot Put SDel
   NewDB();
 
   auto file1 = mock::MakeMockFile({
@@ -924,14 +924,14 @@ TEST_F(CompactionJobTest, MultiSingleDelete) {
       {KeyStr("L", 16U, kTypeSingleDeletion), ""},
       {KeyStr("L", 15U, kTypeValue), "val"},
       {KeyStr("L", 14U, kTypeSingleDeletion), ""},
-      {KeyStr("L", 13U, kTypeDeletion), ""},
+      {KeyStr("L", 13U, kTypeSingleDeletion), ""},
       {KeyStr("L", 12U, kTypeValue), "val"},
-      {KeyStr("L", 11U, kTypeDeletion), ""},
-      {KeyStr("M", 16U, kTypeDeletion), ""},
+      {KeyStr("L", 11U, kTypeSingleDeletion), ""},
+      {KeyStr("M", 16U, kTypeSingleDeletion), ""},
       {KeyStr("M", 15U, kTypeSingleDeletion), ""},
       {KeyStr("M", 14U, kTypeValue), "val"},
       {KeyStr("M", 13U, kTypeSingleDeletion), ""},
-      {KeyStr("M", 12U, kTypeDeletion), ""},
+      {KeyStr("M", 12U, kTypeSingleDeletion), ""},
       {KeyStr("M", 11U, kTypeValue), "val"},
   });
   AddMockFile(file1);
@@ -972,12 +972,12 @@ TEST_F(CompactionJobTest, MultiSingleDelete) {
       {KeyStr("K", 1U, kTypeSingleDeletion), ""},
       {KeyStr("L", 5U, kTypeSingleDeletion), ""},
       {KeyStr("L", 4U, kTypeValue), "val"},
-      {KeyStr("L", 3U, kTypeDeletion), ""},
+      {KeyStr("L", 3U, kTypeSingleDeletion), ""},
       {KeyStr("L", 2U, kTypeValue), "val"},
       {KeyStr("L", 1U, kTypeSingleDeletion), ""},
       {KeyStr("M", 10U, kTypeSingleDeletion), ""},
       {KeyStr("M", 7U, kTypeValue), "val"},
-      {KeyStr("M", 5U, kTypeDeletion), ""},
+      {KeyStr("M", 5U, kTypeSingleDeletion), ""},
       {KeyStr("M", 4U, kTypeValue), "val"},
       {KeyStr("M", 3U, kTypeSingleDeletion), ""},
   });
@@ -1019,7 +1019,9 @@ TEST_F(CompactionJobTest, MultiSingleDelete) {
                           {KeyStr("K", 8U, kTypeValue), "val3"},
                           {KeyStr("L", 16U, kTypeSingleDeletion), ""},
                           {KeyStr("L", 15U, kTypeValue), ""},
-                          {KeyStr("M", 16U, kTypeDeletion), ""},
+                          {KeyStr("L", 11U, kTypeSingleDeletion), ""},
+                          {KeyStr("M", 15U, kTypeSingleDeletion), ""},
+                          {KeyStr("M", 14U, kTypeValue), ""},
                           {KeyStr("M", 3U, kTypeSingleDeletion), ""}});
 
   SetLastSequence(22U);
diff --git a/test_util/transaction_test_util.cc b/test_util/transaction_test_util.cc
index 36b2e9ec4a..3eaa7fd6f9 100644
--- a/test_util/transaction_test_util.cc
+++ b/test_util/transaction_test_util.cc
@@ -91,7 +91,7 @@ Status RandomTransactionInserter::DBGet(
   Status s;
   // Five digits (since the largest uint16_t is 65535) plus the NUL
   // end char.
-  char prefix_buf[6];
+  char prefix_buf[6] = {0};
   // Pad prefix appropriately so we can iterate over each set
   assert(set_i + 1 <= 9999);
   snprintf(prefix_buf, sizeof(prefix_buf), "%.4u", set_i + 1);
@@ -165,7 +165,11 @@ bool RandomTransactionInserter::DoInsert(DB* db, Transaction* txn,
       // Increment key
       std::string sum = ToString(int_value + incr);
       if (txn != nullptr) {
-        s = txn->SingleDelete(key);
+        if ((set_i % 4) != 0) {
+          s = txn->SingleDelete(key);
+        } else {
+          s = txn->Delete(key);
+        }
         if (!get_for_update && (s.IsBusy() || s.IsTimedOut())) {
           // If the initial get was not for update, then the key is not locked
           // before put and put could fail due to concurrent writes.
diff --git a/test_util/transaction_test_util.h b/test_util/transaction_test_util.h
index 086b0ea6f6..175376f5f3 100644
--- a/test_util/transaction_test_util.h
+++ b/test_util/transaction_test_util.h
@@ -33,6 +33,23 @@ class Random64;
 // RandomTransactionInserter with similar arguments using the same DB.
 class RandomTransactionInserter {
  public:
+  static bool RollbackDeletionTypeCallback(const Slice& key) {
+    // These are hard-coded atm. See how RandomTransactionInserter::DoInsert()
+    // determines whether to use SingleDelete or Delete for a key.
+    assert(key.size() >= 4);
+    const char* ptr = key.data();
+    assert(ptr);
+    while (ptr && ptr < key.data() + 4 && *ptr == '0') {
+      ++ptr;
+    }
+    std::string prefix(ptr, 4 - (ptr - key.data()));
+    unsigned long set_i = std::stoul(prefix);
+    assert(set_i > 0);
+    assert(set_i <= 9999);
+    --set_i;
+    return ((set_i % 4) != 0);
+  }
+
   // num_keys is the number of keys in each set.
   // num_sets is the number of sets of keys.
   // cmt_delay_ms is the delay between prepare (if there is any) and commit
diff --git a/utilities/transactions/transaction_test.cc b/utilities/transactions/transaction_test.cc
index 798fb2ad08..20ee73e279 100644
--- a/utilities/transactions/transaction_test.cc
+++ b/utilities/transactions/transaction_test.cc
@@ -5469,6 +5469,10 @@ Status TransactionStressTestInserter(
 TEST_P(MySQLStyleTransactionTest, TransactionStressTest) {
   // Small write buffer to trigger more compactions
   options.write_buffer_size = 1024;
+  txn_db_options.rollback_deletion_type_callback =
+      [](TransactionDB*, ColumnFamilyHandle*, const Slice& key) {
+        return RandomTransactionInserter::RollbackDeletionTypeCallback(key);
+      };
   ASSERT_OK(ReOpenNoDelete());
   constexpr size_t num_workers = 4;        // worker threads count
   constexpr size_t num_checkers = 2;       // checker threads count
diff --git a/utilities/transactions/write_prepared_transaction_test.cc b/utilities/transactions/write_prepared_transaction_test.cc
index 5a90bab885..299b8b3322 100644
--- a/utilities/transactions/write_prepared_transaction_test.cc
+++ b/utilities/transactions/write_prepared_transaction_test.cc
@@ -3202,6 +3202,8 @@ TEST_P(WritePreparedTransactionTest, ReleaseEarliestSnapshotAfterSeqZeroing2) {
 TEST_P(WritePreparedTransactionTest, SingleDeleteAfterRollback) {
   constexpr size_t kSnapshotCacheBits = 7;  // same as default
   constexpr size_t kCommitCacheBits = 0;    // minimum commit cache
+  txn_db_options.rollback_deletion_type_callback =
+      [](TransactionDB*, ColumnFamilyHandle*, const Slice&) { return true; };
   UpdateTransactionDBOptions(kSnapshotCacheBits, kCommitCacheBits);
   options.disable_auto_compactions = true;
   ASSERT_OK(ReOpen());
diff --git a/utilities/transactions/write_unprepared_txn.cc b/utilities/transactions/write_unprepared_txn.cc
index 6cc1603d16..7623c6d733 100644
--- a/utilities/transactions/write_unprepared_txn.cc
+++ b/utilities/transactions/write_unprepared_txn.cc
@@ -675,7 +675,11 @@ Status WriteUnpreparedTxn::WriteRollbackKeys(
       s = rollback_batch->Put(cf_handle, key, pinnable_val);
       assert(s.ok());
     } else if (s.IsNotFound()) {
-      s = rollback_batch->Delete(cf_handle, key);
+      if (wupt_db_->ShouldRollbackWithSingleDelete(cf_handle, key)) {
+        s = rollback_batch->SingleDelete(cf_handle, key);
+      } else {
+        s = rollback_batch->Delete(cf_handle, key);
+      }
       assert(s.ok());
     } else {
       return s;