diff --git a/compaction_iter.go b/compaction_iter.go
index cadb9b03a2..522557bfeb 100644
--- a/compaction_iter.go
+++ b/compaction_iter.go
@@ -7,6 +7,7 @@ package pebble
 import (
 	"io"
 	"sort"
+	"strconv"
 
 	"github.com/cockroachdb/errors"
 	"github.com/cockroachdb/pebble/internal/base"
@@ -140,6 +141,10 @@ type compactionIter struct {
 	// determine when iteration has advanced to a new user key and thus a new
 	// snapshot stripe.
 	keyBuf []byte
+	// Temporary buffer used for storing the previous value, which may be an
+	// unsafe, i.iter-owned slice that could be altered when the iterator is
+	// advanced.
+	valueBuf []byte
 	// Is the current entry valid?
 	valid     bool
 	iterKey   *InternalKey
@@ -303,12 +308,8 @@ func (i *compactionIter) Next() (*InternalKey, []byte) {
 				continue
 			}
 
-		case InternalKeyKindSet:
-			i.saveKey()
-			i.value = i.iterValue
-			i.valid = true
-			i.skip = true
-			i.maybeZeroSeqnum(i.curSnapshotIdx)
+		case InternalKeyKindSet, InternalKeyKindSetWithDelete:
+			i.setNext()
 			return &i.key, i.value
 
 		case InternalKeyKindMerge:
@@ -444,6 +445,52 @@ func (i *compactionIter) nextInStripe() stripeChangeType {
 	return newStripe
 }
 
+func (i *compactionIter) setNext() {
+	// Save the current key.
+	i.saveKey()
+	// iterValue is owned by i.iter and could change after the Next() call, so
+	// use valueBuf instead. Note that valueBuf is only used in this one
+	// instance; everywhere else, we just point i.value to the unsafe
+	// i.iter-owned value buffer.
+	i.valueBuf = append(i.valueBuf[:0], i.iterValue...)
+	i.value = i.valueBuf
+	i.valid = true
+	i.maybeZeroSeqnum(i.curSnapshotIdx)
+
+	// If this key is a SETWITHDEL, we can emit it immediately. Records with the
+	// same key are safe to skip.
+	if i.iterKey.Kind() == InternalKeyKindSetWithDelete {
+		i.skip = true
+		return
+	}
+
+	// Else, we continue to loop through records in the stripe.
+	for {
+		switch t := i.nextInStripe(); t {
+		case newStripe, sameStripeNonSkippable:
+			i.pos = iterPosNext
+			if t == sameStripeNonSkippable {
+				// This is a key we cannot skip. We can safely emit a SETWITHDEL
+				// here, though it is suboptimal due to ... FIXME
+				// TODO(travers): Optimize this after undertaking a larger
+				// refactoring to make this check simpler.
+				i.key.SetKind(InternalKeyKindSetWithDelete)
+			}
+			return
+		case sameStripeSkippable:
+			// We're still in the same stripe. If this is a DEL, we stop looking
+			// and emit a SETWITHDEL. Subsequent keys are eligible for skipping.
+			if i.iterKey.Kind() == InternalKeyKindDelete {
+				i.key.SetKind(InternalKeyKindSetWithDelete)
+				i.skip = true
+				return
+			}
+		default:
+			panic("pebble: unexpected stripeChangeType: " + strconv.Itoa(int(t)))
+		}
+	}
+}
+
 func (i *compactionIter) mergeNext(valueMerger ValueMerger) stripeChangeType {
 	// Save the current key.
 	i.saveKey()
@@ -479,7 +526,7 @@ func (i *compactionIter) mergeNext(valueMerger ValueMerger) stripeChangeType {
 			i.skip = true
 			return sameStripeSkippable
 
-		case InternalKeyKindSet:
+		case InternalKeyKindSet, InternalKeyKindSetWithDelete:
 			if i.rangeDelFrag.Deleted(*key, i.curSnapshotSeqNum) {
 				// We change the kind of the result key to a Set so that it shadows
 				// keys in lower levels. That is, MERGE+RANGEDEL -> SET. This isn't
@@ -490,9 +537,10 @@ func (i *compactionIter) mergeNext(valueMerger ValueMerger) stripeChangeType {
 				return sameStripeSkippable
 			}
 
-			// We've hit a Set value. Merge with the existing value and return. We
-			// change the kind of the resulting key to a Set so that it shadows keys
-			// in lower levels. That is, MERGE+SET -> SET.
+			// We've hit a Set or SetWithDel value. Merge with the existing
+			// value and return. We change the kind of the resulting key to a
+			// Set so that it shadows keys in lower levels. That is:
+			// MERGE + (SET*) -> SET.
 			i.err = valueMerger.MergeOlder(i.iterValue)
 			if i.err != nil {
 				i.valid = false
@@ -544,8 +592,9 @@ func (i *compactionIter) singleDeleteNext() bool {
 
 		key := i.iterKey
 		switch key.Kind() {
-		case InternalKeyKindDelete, InternalKeyKindMerge:
-			// We've hit a Delete or Merge, transform the SingleDelete into a full Delete.
+		case InternalKeyKindDelete, InternalKeyKindMerge, InternalKeyKindSetWithDelete:
+			// We've hit a Delete, Merge or SetWithDelete, transform the
+			// SingleDelete into a full Delete.
 			i.key.SetKind(InternalKeyKindDelete)
 			i.skip = true
 			return true
diff --git a/error_test.go b/error_test.go
index 165f5a83ca..15bf755468 100644
--- a/error_test.go
+++ b/error_test.go
@@ -194,7 +194,7 @@ func TestRequireReadError(t *testing.T) {
 		require.NoError(t, d.Flush())
 		expectLSM(`
 0.0:
-  000007:[a1#4,SET-a2#72057594037927935,RANGEDEL]
+  000007:[a1#4,SETWITHDEL-a2#72057594037927935,RANGEDEL]
 6:
   000005:[a1#1,SET-a2#2,SET]
 `, d, t)
@@ -281,7 +281,7 @@ func TestCorruptReadError(t *testing.T) {
 		require.NoError(t, d.Flush())
 		expectLSM(`
 0.0:
-  000007:[a1#4,SET-a2#72057594037927935,RANGEDEL]
+  000007:[a1#4,SETWITHDEL-a2#72057594037927935,RANGEDEL]
 6:
   000005:[a1#1,SET-a2#2,SET]
 `, d, t)
diff --git a/internal.go b/internal.go
index 00e38b33b8..563785ee67 100644
--- a/internal.go
+++ b/internal.go
@@ -18,6 +18,7 @@ const (
 	InternalKeyKindSingleDelete    = base.InternalKeyKindSingleDelete
 	InternalKeyKindRangeDelete     = base.InternalKeyKindRangeDelete
 	InternalKeyKindMax             = base.InternalKeyKindMax
+	InternalKeyKindSetWithDelete   = base.InternalKeyKindSetWithDelete
 	InternalKeyKindInvalid         = base.InternalKeyKindInvalid
 	InternalKeySeqNumBatch         = base.InternalKeySeqNumBatch
 	InternalKeySeqNumMax           = base.InternalKeySeqNumMax
diff --git a/internal/base/internal.go b/internal/base/internal.go
index 3afd6f38b5..448e85d605 100644
--- a/internal/base/internal.go
+++ b/internal/base/internal.go
@@ -47,6 +47,11 @@ const (
 	// seqNum.
 	InternalKeyKindMax InternalKeyKind = 17
 
+	// InternalKeyKindSetWithDelete keys are SET keys that have met with a
+	// DELETE key in a prior compaction. This key kind is specific to Pebble.
+	// See https://github.com/cockroachdb/pebble/issues/1255.
+	InternalKeyKindSetWithDelete InternalKeyKind = 18
+
 	// A marker for an invalid key.
 	InternalKeyKindInvalid InternalKeyKind = 255
 
@@ -66,14 +71,15 @@ const (
 )
 
 var internalKeyKindNames = []string{
-	InternalKeyKindDelete:       "DEL",
-	InternalKeyKindSet:          "SET",
-	InternalKeyKindMerge:        "MERGE",
-	InternalKeyKindLogData:      "LOGDATA",
-	InternalKeyKindSingleDelete: "SINGLEDEL",
-	InternalKeyKindRangeDelete:  "RANGEDEL",
-	InternalKeyKindMax:          "MAX",
-	InternalKeyKindInvalid:      "INVALID",
+	InternalKeyKindDelete:        "DEL",
+	InternalKeyKindSet:           "SET",
+	InternalKeyKindMerge:         "MERGE",
+	InternalKeyKindLogData:       "LOGDATA",
+	InternalKeyKindSingleDelete:  "SINGLEDEL",
+	InternalKeyKindRangeDelete:   "RANGEDEL",
+	InternalKeyKindMax:           "MAX",
+	InternalKeyKindSetWithDelete: "SETWITHDEL",
+	InternalKeyKindInvalid:       "INVALID",
 }
 
 func (k InternalKeyKind) String() string {
@@ -130,13 +136,14 @@ func MakeRangeDeleteSentinelKey(userKey []byte) InternalKey {
 }
 
 var kindsMap = map[string]InternalKeyKind{
-	"DEL":       InternalKeyKindDelete,
-	"SINGLEDEL": InternalKeyKindSingleDelete,
-	"RANGEDEL":  InternalKeyKindRangeDelete,
-	"SET":       InternalKeyKindSet,
-	"MERGE":     InternalKeyKindMerge,
-	"INVALID":   InternalKeyKindInvalid,
-	"MAX":       InternalKeyKindMax,
+	"DEL":        InternalKeyKindDelete,
+	"SINGLEDEL":  InternalKeyKindSingleDelete,
+	"RANGEDEL":   InternalKeyKindRangeDelete,
+	"SET":        InternalKeyKindSet,
+	"MERGE":      InternalKeyKindMerge,
+	"INVALID":    InternalKeyKindInvalid,
+	"MAX":        InternalKeyKindMax,
+	"SETWITHDEL": InternalKeyKindSetWithDelete,
 }
 
 // ParseInternalKey parses the string representation of an internal key. The
diff --git a/iterator.go b/iterator.go
index 6bfa85eb9c..4d7ebfb9b8 100644
--- a/iterator.go
+++ b/iterator.go
@@ -245,7 +245,7 @@ func (i *Iterator) findNextEntry(limit []byte) {
 			i.nextUserKey()
 			continue
 
-		case InternalKeyKindSet:
+		case InternalKeyKindSet, InternalKeyKindSetWithDelete:
 			i.keyBuf = append(i.keyBuf[:0], key.UserKey...)
 			i.key = i.keyBuf
 			i.value = i.iterValue
@@ -459,7 +459,7 @@ func (i *Iterator) findPrevEntry(limit []byte) {
 			}
 			continue
 
-		case InternalKeyKindSet:
+		case InternalKeyKindSet, InternalKeyKindSetWithDelete:
 			i.keyBuf = append(i.keyBuf[:0], key.UserKey...)
 			i.key = i.keyBuf
 			// iterValue is owned by i.iter and could change after the Prev()
@@ -570,7 +570,7 @@ func (i *Iterator) mergeNext(key InternalKey, valueMerger ValueMerger) {
 			// point.
 			return
 
-		case InternalKeyKindSet:
+		case InternalKeyKindSet, InternalKeyKindSetWithDelete:
 			// We've hit a Set value. Merge with the existing value and return.
 			i.err = valueMerger.MergeOlder(i.iterValue)
 			return
diff --git a/level_checker.go b/level_checker.go
index d779546e5e..dcf6010995 100644
--- a/level_checker.go
+++ b/level_checker.go
@@ -167,7 +167,7 @@ func (m *simpleMergingIter) step() bool {
 					m.err = closer.Close()
 				}
 				m.valueMerger = nil
-			case InternalKeyKindSet:
+			case InternalKeyKindSet, InternalKeyKindSetWithDelete:
 				m.err = m.valueMerger.MergeOlder(item.value)
 				if m.err == nil {
 					var closer io.Closer
diff --git a/range_del_test.go b/range_del_test.go
index dd406e9ffa..1afdcd0c56 100644
--- a/range_del_test.go
+++ b/range_del_test.go
@@ -264,9 +264,9 @@ func TestRangeDelCompactionTruncation(t *testing.T) {
 1:
   000012:[a#3,RANGEDEL-b#72057594037927935,RANGEDEL]
 3:
-  000017:[b#4,SET-b#4,SET]
+  000017:[b#4,SETWITHDEL-b#4,SETWITHDEL]
   000018:[b#3,RANGEDEL-c#72057594037927935,RANGEDEL]
-  000019:[c#5,SET-d#72057594037927935,RANGEDEL]
+  000019:[c#5,SETWITHDEL-d#72057594037927935,RANGEDEL]
 `)
 
 	// The L1 table still contains a tombstone from [a,d) which will improperly
diff --git a/testdata/compaction_iter b/testdata/compaction_iter
index e7038e8cd1..3ecbc85927 100644
--- a/testdata/compaction_iter
+++ b/testdata/compaction_iter
@@ -169,7 +169,7 @@ iter
 first
 next
 ----
-a#9,1:b
+a#9,18:b
 .
 
 iter snapshots=6
@@ -177,7 +177,7 @@ first
 next
 next
 ----
-a#9,1:b
+a#9,18:b
 a#5,1:f
 .
 
@@ -186,7 +186,7 @@ first
 next
 next
 ----
-a#9,1:b
+a#9,18:b
 a#6,0:
 .
 
@@ -195,8 +195,8 @@ first
 next
 next
 ----
-a#9,1:b
-a#7,1:d
+a#9,18:b
+a#7,18:d
 .
 
 iter snapshots=9
@@ -212,7 +212,7 @@ iter snapshots=10
 first
 next
 ----
-a#9,1:b
+a#9,18:b
 .
 
 iter snapshots=(5,6,7,8,9)
@@ -249,7 +249,7 @@ iter
 first
 next
 ----
-a#2,1:b
+a#2,18:b
 err=invalid internal key kind: 255
 
 define
@@ -308,7 +308,7 @@ next
 next
 tombstones
 ----
-a#2,1:b
+a#2,18:b
 a#1,15:c
 b#4,15:d
 .
@@ -342,7 +342,7 @@ next
 next
 tombstones
 ----
-a#2,1:b
+a#2,18:b
 a#1,15:c
 b#4,15:d
 b#2,1:e
@@ -362,7 +362,7 @@ next
 next
 tombstones
 ----
-a#2,1:b
+a#2,18:b
 a#1,15:c
 b#4,15:d
 b#2,1:e
@@ -1164,3 +1164,173 @@ next
 a#3,15:c
 b#5,1:5[base]
 b#1,2:1
+
+# SET that meets a DEL is transformed into a SETWITHDEL.
+
+define
+a.SET.2:b
+a.DEL.1:
+----
+
+iter
+first
+next
+----
+a#2,18:b
+.
+
+iter snapshots=2
+first
+next
+next
+----
+a#2,1:b
+a#1,0:
+.
+
+define
+a.SET.3:c
+a.DEL.2:
+a.SET.1:b
+----
+
+iter
+first
+next
+----
+a#3,18:c
+.
+
+iter snapshots=2
+first
+next
+next
+----
+a#3,18:c
+a#1,1:b
+.
+
+define
+a.SET.3:c
+a.SET.2:b
+a.DEL.1:
+----
+
+iter
+first
+next
+----
+a#3,18:c
+.
+
+iter snapshots=3
+first
+next
+next
+----
+a#3,1:c
+a#2,18:b
+.
+
+iter snapshots=2
+first
+next
+next
+----
+a#3,1:c
+a#1,0:
+.
+
+define
+a.DEL.3:
+a.SET.2:b
+a.DEL.1:
+----
+
+iter
+first
+next
+----
+a#3,0:
+.
+
+iter snapshots=3
+first
+next
+next
+----
+a#3,0:
+a#2,18:b
+.
+
+iter snapshots=2
+first
+next
+next
+----
+a#3,0:
+a#1,0:
+.
+
+# SINGLEDEL that meets a SETWITHDEL is transformed into a DEL.
+
+define
+a.SINGLEDEL.3:
+a.SETWITHDEL.2:d
+b.SET.1:c
+----
+
+iter
+first
+next
+next
+----
+a#3,0:
+b#1,1:c
+.
+
+iter snapshots=2
+first
+next
+next
+----
+a#3,0:
+b#1,1:c
+.
+
+iter snapshots=3
+first
+next
+next
+next
+----
+a#3,7:
+a#2,18:d
+b#1,1:c
+.
+
+define
+a.SETWITHDEL.3:3
+a.SET.2:d
+b.SET.1:c
+----
+
+iter
+first
+next
+next
+----
+a#3,18:3
+b#1,1:c
+.
+
+iter snapshots=3
+first
+next
+next
+next
+----
+a#3,18:3
+a#2,1:d
+b#1,1:c
+.
diff --git a/testdata/manual_compaction b/testdata/manual_compaction
index 594c742d1a..0e75649cc3 100644
--- a/testdata/manual_compaction
+++ b/testdata/manual_compaction
@@ -92,7 +92,7 @@ range-deletions-bytes-estimate: 1552
 compact a-e L1
 ----
 2:
-  000008:[a#3,SET-b#72057594037927935,RANGEDEL]
+  000008:[a#3,SETWITHDEL-b#72057594037927935,RANGEDEL]
   000009:[b#2,RANGEDEL-d#72057594037927935,RANGEDEL]
   000010:[d#2,RANGEDEL-e#72057594037927935,RANGEDEL]
 3:
@@ -140,7 +140,7 @@ L3
 compact a-e L1
 ----
 2:
-  000010:[a#3,SET-b#72057594037927935,RANGEDEL]
+  000010:[a#3,SETWITHDEL-b#72057594037927935,RANGEDEL]
   000011:[b#2,RANGEDEL-d#72057594037927935,RANGEDEL]
   000012:[d#2,RANGEDEL-f#72057594037927935,RANGEDEL]
   000013:[f#2,RANGEDEL-g#72057594037927935,RANGEDEL]
@@ -181,7 +181,7 @@ L3
 compact a-e L1
 ----
 2:
-  000009:[a#3,SET-g#72057594037927935,RANGEDEL]
+  000009:[a#3,SETWITHDEL-g#72057594037927935,RANGEDEL]
   000010:[h#3,SET-h#3,SET]
 3:
   000006:[a#0,SET-b#0,SET]
@@ -390,7 +390,7 @@ compact a-e L1
 0.0:
   000004:[c#4,SET-c#4,SET]
 2:
-  000008:[a#3,SET-b#72057594037927935,RANGEDEL]
+  000008:[a#3,SETWITHDEL-b#72057594037927935,RANGEDEL]
   000009:[b#2,RANGEDEL-e#72057594037927935,RANGEDEL]
 3:
   000007:[b#1,SET-b#1,SET]
diff --git a/testdata/singledel_manual_compaction b/testdata/singledel_manual_compaction
index ff83e37648..067958023a 100644
--- a/testdata/singledel_manual_compaction
+++ b/testdata/singledel_manual_compaction
@@ -1,7 +1,6 @@
 # This is not actually a manual compaction test, and simply uses manual
-# compaction to demonstrate single delete semantics. Specifically, it
-# demonstrates that the behavior can be non-deterministic if not used
-# correctly.
+# compaction to demonstrate single delete semantics with used with
+# set-with-delete.
 
 # Define a sequence of SET=>SET=>DEL=>SET=>SINGLEDEL.
 define target-file-sizes=(1, 1, 1, 1, 1)
@@ -39,7 +38,7 @@ compact a-b L2
 1:
   000004:[a#10,SINGLEDEL-a#10,SINGLEDEL]
 3:
-  000009:[a#9,SET-a#9,SET]
+  000009:[a#9,SETWITHDEL-a#9,SETWITHDEL]
 4:
   000007:[a#7,SET-a#7,SET]
 5:
@@ -57,7 +56,7 @@ compact a-b L1
 2:
   000010:[a#10,SINGLEDEL-a#10,SINGLEDEL]
 3:
-  000009:[a#9,SET-a#9,SET]
+  000009:[a#9,SETWITHDEL-a#9,SETWITHDEL]
 4:
   000007:[a#7,SET-a#7,SET]
 5:
@@ -65,13 +64,15 @@ compact a-b L1
 
 compact a-b L2
 ----
+3:
+  000011:[a#10,DEL-a#10,DEL]
 4:
   000007:[a#7,SET-a#7,SET]
 5:
   000008:[a#6,SET-a#6,SET]
 
-# Deleted data reappears.
+# Deleted data is not resurrected.
 iter
 first
 ----
-a:v2
+.
diff --git a/tool/find.go b/tool/find.go
index 214f9a256f..8714a5b757 100644
--- a/tool/find.go
+++ b/tool/find.go
@@ -345,7 +345,8 @@ func (f *findT) searchLogs(searchKey []byte, refs []findRef) []findRef {
 					case base.InternalKeyKindDelete,
 						base.InternalKeyKindSet,
 						base.InternalKeyKindMerge,
-						base.InternalKeyKindSingleDelete:
+						base.InternalKeyKindSingleDelete,
+						base.InternalKeyKindSetWithDelete:
 						if cmp(searchKey, ikey.UserKey) != 0 {
 							continue
 						}
diff --git a/tool/wal.go b/tool/wal.go
index 28092eef42..d701174bba 100644
--- a/tool/wal.go
+++ b/tool/wal.go
@@ -138,6 +138,8 @@ func (w *walT) runDump(cmd *cobra.Command, args []string) {
 						fmt.Fprintf(stdout, "<%d>", len(value))
 					case base.InternalKeyKindSingleDelete:
 						fmt.Fprintf(stdout, "%s", w.fmtKey.fn(ukey))
+					case base.InternalKeyKindSetWithDelete:
+						fmt.Fprintf(stdout, "%s", w.fmtKey.fn(ukey))
 					case base.InternalKeyKindRangeDelete:
 						fmt.Fprintf(stdout, "%s,%s", w.fmtKey.fn(ukey), w.fmtKey.fn(value))
 					}