diff --git a/server/mvcc/hash.go b/server/mvcc/hash.go
index 11232bf5677..8af5d90a46f 100644
--- a/server/mvcc/hash.go
+++ b/server/mvcc/hash.go
@@ -62,6 +62,9 @@ func (h *kvHasher) WriteKeyValue(k, v []byte) {
 	if !upper.GreaterThan(kr) {
 		return
 	}
+
+	isTombstoneRev := isTombstone(k)
+
 	lower := revision{main: h.compactRevision + 1}
 	// skip revisions that are scheduled for deletion
 	// due to compacting; don't skip if there isn't one.
@@ -70,6 +73,17 @@ func (h *kvHasher) WriteKeyValue(k, v []byte) {
 			return
 		}
 	}
+
+	// When performing compaction, if the compacted revision is a
+	// tombstone, older versions (<= 3.5.15 or <= 3.4.33) will delete
+	// the tombstone. But newer versions (> 3.5.15 or > 3.4.33) won't
+	// delete it. So we should skip the tombstone in such cases when
+	// computing the hash to ensure that both older and newer versions
+	// can always generate the same hash values.
+	if kr.main == h.compactRevision && isTombstoneRev {
+		return
+	}
+
 	h.hash.Write(k)
 	h.hash.Write(v)
 }
diff --git a/server/mvcc/index_test.go b/server/mvcc/index_test.go
index 87c31dd905f..c2749276cbd 100644
--- a/server/mvcc/index_test.go
+++ b/server/mvcc/index_test.go
@@ -18,8 +18,9 @@ import (
 	"reflect"
 	"testing"
 
-	"github.com/google/btree"
+	"github.com/stretchr/testify/require"
 	"go.uber.org/zap"
+	"go.uber.org/zap/zaptest"
 )
 
 func TestIndexGet(t *testing.T) {
@@ -196,98 +197,445 @@ func TestIndexRangeSince(t *testing.T) {
 
 func TestIndexCompactAndKeep(t *testing.T) {
 	maxRev := int64(20)
-	tests := []struct {
-		key     []byte
-		remove  bool
-		rev     revision
-		created revision
-		ver     int64
+
+	// key: "foo"
+	// modified: 10
+	// generations:
+	//	{{10, 0}}
+	//	{{1, 0}, {5, 0}, {9, 0}(t)}
+	//
+	// key: "foo1"
+	// modified: 10, 1
+	// generations:
+	//	{{10, 1}}
+	//	{{2, 0}, {6, 0}, {7, 0}(t)}
+	//
+	// key: "foo2"
+	// modified: 8
+	// generations:
+	//	{empty}
+	//	{{3, 0}, {4, 0}, {8, 0}(t)}
+	//
+	buildTreeIndex := func() index {
+		ti := newTreeIndex(zaptest.NewLogger(t))
+
+		ti.Put([]byte("foo"), revision{main: 1})
+		ti.Put([]byte("foo1"), revision{main: 2})
+		ti.Put([]byte("foo2"), revision{main: 3})
+		ti.Put([]byte("foo2"), revision{main: 4})
+		ti.Put([]byte("foo"), revision{main: 5})
+		ti.Put([]byte("foo1"), revision{main: 6})
+		require.NoError(t, ti.Tombstone([]byte("foo1"), revision{main: 7}))
+		require.NoError(t, ti.Tombstone([]byte("foo2"), revision{main: 8}))
+		require.NoError(t, ti.Tombstone([]byte("foo"), revision{main: 9}))
+		ti.Put([]byte("foo"), revision{main: 10})
+		ti.Put([]byte("foo1"), revision{main: 10, sub: 1})
+		return ti
+	}
+
+	afterCompacts := []struct {
+		atRev      int
+		keyIndexes []keyIndex
+		keep       map[revision]struct{}
+		compacted  map[revision]struct{}
 	}{
-		{[]byte("foo"), false, revision{main: 1}, revision{main: 1}, 1},
-		{[]byte("foo1"), false, revision{main: 2}, revision{main: 2}, 1},
-		{[]byte("foo2"), false, revision{main: 3}, revision{main: 3}, 1},
-		{[]byte("foo2"), false, revision{main: 4}, revision{main: 3}, 2},
-		{[]byte("foo"), false, revision{main: 5}, revision{main: 1}, 2},
-		{[]byte("foo1"), false, revision{main: 6}, revision{main: 2}, 2},
-		{[]byte("foo1"), true, revision{main: 7}, revision{}, 0},
-		{[]byte("foo2"), true, revision{main: 8}, revision{}, 0},
-		{[]byte("foo"), true, revision{main: 9}, revision{}, 0},
-		{[]byte("foo"), false, revision{10, 0}, revision{10, 0}, 1},
-		{[]byte("foo1"), false, revision{10, 1}, revision{10, 1}, 1},
+		{
+			atRev: 1,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 1}, revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 2}, revision{main: 6}, revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 3}, revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 1}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 1}: {},
+			},
+		},
+		{
+			atRev: 2,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 1}, revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 2}, revision{main: 6}, revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 3}, revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 1}: {},
+				revision{main: 2}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 1}: {},
+				revision{main: 2}: {},
+			},
+		},
+		{
+			atRev: 3,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 1}, revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 2}, revision{main: 6}, revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 3}, revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 1}: {},
+				revision{main: 2}: {},
+				revision{main: 3}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 1}: {},
+				revision{main: 2}: {},
+				revision{main: 3}: {},
+			},
+		},
+		{
+			atRev: 4,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 1}, revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 2}, revision{main: 6}, revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 1}: {},
+				revision{main: 2}: {},
+				revision{main: 4}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 1}: {},
+				revision{main: 2}: {},
+				revision{main: 4}: {},
+			},
+		},
+		{
+			atRev: 5,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 2}, revision{main: 6}, revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 2}: {},
+				revision{main: 4}: {},
+				revision{main: 5}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 2}: {},
+				revision{main: 4}: {},
+				revision{main: 5}: {},
+			},
+		},
+		{
+			atRev: 6,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 6}, revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 6}: {},
+				revision{main: 4}: {},
+				revision{main: 5}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 6}: {},
+				revision{main: 4}: {},
+				revision{main: 5}: {},
+			},
+		},
+		{
+			atRev: 7,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 3, created: revision{main: 2}, revs: []revision{revision{main: 7}}},
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 4}, revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 4}: {},
+				revision{main: 5}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 7}: {},
+				revision{main: 4}: {},
+				revision{main: 5}: {},
+			},
+		},
+		{
+			atRev: 8,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 5}, revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+				{
+					key:      []byte("foo2"),
+					modified: revision{main: 8},
+					generations: []generation{
+						{ver: 3, created: revision{main: 3}, revs: []revision{revision{main: 8}}},
+						{},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 5}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 8}: {},
+				revision{main: 5}: {},
+			},
+		},
+		{
+			atRev: 9,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 3, created: revision{main: 1}, revs: []revision{revision{main: 9}}},
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+			},
+			keep: map[revision]struct{}{},
+			compacted: map[revision]struct{}{
+				revision{main: 9}: {},
+			},
+		},
+		{
+			atRev: 10,
+			keyIndexes: []keyIndex{
+				{
+					key:      []byte("foo"),
+					modified: revision{main: 10},
+					generations: []generation{
+						{ver: 1, created: revision{main: 10}, revs: []revision{revision{main: 10}}},
+					},
+				},
+				{
+					key:      []byte("foo1"),
+					modified: revision{main: 10, sub: 1},
+					generations: []generation{
+						{ver: 1, created: revision{main: 10, sub: 1}, revs: []revision{revision{main: 10, sub: 1}}},
+					},
+				},
+			},
+			keep: map[revision]struct{}{
+				revision{main: 10}:         {},
+				revision{main: 10, sub: 1}: {},
+			},
+			compacted: map[revision]struct{}{
+				revision{main: 10}:         {},
+				revision{main: 10, sub: 1}: {},
+			},
+		},
 	}
 
+	ti := buildTreeIndex()
 	// Continuous Compact and Keep
-	ti := newTreeIndex(zap.NewExample())
-	for _, tt := range tests {
-		if tt.remove {
-			ti.Tombstone(tt.key, tt.rev)
-		} else {
-			ti.Put(tt.key, tt.rev)
-		}
-	}
 	for i := int64(1); i < maxRev; i++ {
+		j := i - 1
+		if i >= int64(len(afterCompacts)) {
+			j = int64(len(afterCompacts)) - 1
+		}
+
 		am := ti.Compact(i)
+		require.Equal(t, afterCompacts[j].compacted, am, "#%d: compact(%d) != expected", i, i)
+
 		keep := ti.Keep(i)
-		if !(reflect.DeepEqual(am, keep)) {
-			t.Errorf("#%d: compact keep %v != Keep keep %v", i, am, keep)
-		}
-		wti := &treeIndex{tree: btree.New(32)}
-		for _, tt := range tests {
-			if _, ok := am[tt.rev]; ok || tt.rev.GreaterThan(revision{main: i}) {
-				if tt.remove {
-					wti.Tombstone(tt.key, tt.rev)
-				} else {
-					restore(wti, tt.key, tt.created, tt.rev, tt.ver)
-				}
-			}
-		}
-		if !ti.Equal(wti) {
-			t.Errorf("#%d: not equal ti", i)
+		require.Equal(t, afterCompacts[j].keep, keep, "#%d: keep(%d) != expected", i, i)
+
+		nti := newTreeIndex(zaptest.NewLogger(t)).(*treeIndex)
+		for k := range afterCompacts[j].keyIndexes {
+			ki := afterCompacts[j].keyIndexes[k]
+			nti.tree.ReplaceOrInsert(&ki)
 		}
+		require.True(t, ti.Equal(nti), "#%d: not equal ti", i)
 	}
 
 	// Once Compact and Keep
 	for i := int64(1); i < maxRev; i++ {
-		ti := newTreeIndex(zap.NewExample())
-		for _, tt := range tests {
-			if tt.remove {
-				ti.Tombstone(tt.key, tt.rev)
-			} else {
-				ti.Put(tt.key, tt.rev)
-			}
+		ti := buildTreeIndex()
+
+		j := i - 1
+		if i >= int64(len(afterCompacts)) {
+			j = int64(len(afterCompacts)) - 1
 		}
+
 		am := ti.Compact(i)
+		require.Equal(t, afterCompacts[j].compacted, am, "#%d: compact(%d) != expected", i, i)
+
 		keep := ti.Keep(i)
-		if !(reflect.DeepEqual(am, keep)) {
-			t.Errorf("#%d: compact keep %v != Keep keep %v", i, am, keep)
-		}
-		wti := &treeIndex{tree: btree.New(32)}
-		for _, tt := range tests {
-			if _, ok := am[tt.rev]; ok || tt.rev.GreaterThan(revision{main: i}) {
-				if tt.remove {
-					wti.Tombstone(tt.key, tt.rev)
-				} else {
-					restore(wti, tt.key, tt.created, tt.rev, tt.ver)
-				}
-			}
-		}
-		if !ti.Equal(wti) {
-			t.Errorf("#%d: not equal ti", i)
-		}
-	}
-}
+		require.Equal(t, afterCompacts[j].keep, keep, "#%d: keep(%d) != expected", i, i)
 
-func restore(ti *treeIndex, key []byte, created, modified revision, ver int64) {
-	keyi := &keyIndex{key: key}
+		nti := newTreeIndex(zaptest.NewLogger(t)).(*treeIndex)
+		for k := range afterCompacts[j].keyIndexes {
+			ki := afterCompacts[j].keyIndexes[k]
+			nti.tree.ReplaceOrInsert(&ki)
+		}
 
-	ti.Lock()
-	defer ti.Unlock()
-	item := ti.tree.Get(keyi)
-	if item == nil {
-		keyi.restore(ti.lg, created, modified, ver)
-		ti.tree.ReplaceOrInsert(keyi)
-		return
+		require.True(t, ti.Equal(nti), "#%d: not equal ti", i)
 	}
-	okeyi := item.(*keyIndex)
-	okeyi.put(ti.lg, modified.main, modified.sub)
 }
diff --git a/server/mvcc/key_index.go b/server/mvcc/key_index.go
index daec9782586..d38b0933d92 100644
--- a/server/mvcc/key_index.go
+++ b/server/mvcc/key_index.go
@@ -66,7 +66,8 @@ var (
 // compact(5):
 // generations:
 //
-//	{empty} -> key SHOULD be removed.
+//	{empty}
+//	{5.0(t)}
 //
 // compact(6):
 // generations:
@@ -203,8 +204,7 @@ func (ki *keyIndex) since(lg *zap.Logger, rev int64) []revision {
 }
 
 // compact compacts a keyIndex by removing the versions with smaller or equal
-// revision than the given atRev except the largest one (If the largest one is
-// a tombstone, it will not be kept).
+// revision than the given atRev except the largest one.
 // If a generation becomes empty during compaction, it will be removed.
 func (ki *keyIndex) compact(lg *zap.Logger, atRev int64, available map[revision]struct{}) {
 	if ki.isEmpty() {
@@ -222,11 +222,6 @@ func (ki *keyIndex) compact(lg *zap.Logger, atRev int64, available map[revision]
 		if revIndex != -1 {
 			g.revs = g.revs[revIndex:]
 		}
-		// remove any tombstone
-		if len(g.revs) == 1 && genIdx != len(ki.generations)-1 {
-			delete(available, g.revs[0])
-			genIdx++
-		}
 	}
 
 	// remove the previous generations.
@@ -242,7 +237,12 @@ func (ki *keyIndex) keep(atRev int64, available map[revision]struct{}) {
 	genIdx, revIndex := ki.doCompact(atRev, available)
 	g := &ki.generations[genIdx]
 	if !g.isEmpty() {
-		// remove any tombstone
+		// If the given `atRev` is a tombstone, we need to skip it.
+		//
+		// Note that this s different from the `compact` function which
+		// keeps tombstone in such case. We need to stay consistent with
+		// existing versions, ensuring they always generate the same hash
+		// values.
 		if revIndex == len(g.revs)-1 && genIdx != len(ki.generations)-1 {
 			delete(available, g.revs[revIndex])
 		}
@@ -263,7 +263,7 @@ func (ki *keyIndex) doCompact(atRev int64, available map[revision]struct{}) (gen
 	genIdx, g := 0, &ki.generations[0]
 	// find first generation includes atRev or created after atRev
 	for genIdx < len(ki.generations)-1 {
-		if tomb := g.revs[len(g.revs)-1].main; tomb > atRev {
+		if tomb := g.revs[len(g.revs)-1].main; tomb >= atRev {
 			break
 		}
 		genIdx++
diff --git a/server/mvcc/key_index_test.go b/server/mvcc/key_index_test.go
index 6404752ed36..814e252fd4a 100644
--- a/server/mvcc/key_index_test.go
+++ b/server/mvcc/key_index_test.go
@@ -18,6 +18,7 @@ import (
 	"reflect"
 	"testing"
 
+	"github.com/stretchr/testify/assert"
 	"go.uber.org/zap"
 )
 
@@ -298,12 +299,15 @@ func TestKeyIndexCompactAndKeep(t *testing.T) {
 				key:      []byte("foo"),
 				modified: revision{16, 0},
 				generations: []generation{
+					{created: revision{main: 2}, ver: 3, revs: []revision{revision{main: 6}}},
 					{created: revision{8, 0}, ver: 3, revs: []revision{{main: 8}, {main: 10}, {main: 12}}},
 					{created: revision{14, 0}, ver: 3, revs: []revision{{main: 14}, {main: 15, sub: 1}, {main: 16}}},
 					{},
 				},
 			},
-			map[revision]struct{}{},
+			map[revision]struct{}{
+				{main: 6}: {},
+			},
 		},
 		{
 			7,
@@ -384,11 +388,14 @@ func TestKeyIndexCompactAndKeep(t *testing.T) {
 				key:      []byte("foo"),
 				modified: revision{16, 0},
 				generations: []generation{
+					{created: revision{main: 8}, ver: 3, revs: []revision{revision{main: 12}}},
 					{created: revision{14, 0}, ver: 3, revs: []revision{{main: 14}, {main: 15, sub: 1}, {main: 16}}},
 					{},
 				},
 			},
-			map[revision]struct{}{},
+			map[revision]struct{}{
+				{main: 12}: {},
+			},
 		},
 		{
 			13,
@@ -434,7 +441,21 @@ func TestKeyIndexCompactAndKeep(t *testing.T) {
 			16,
 			&keyIndex{
 				key:      []byte("foo"),
-				modified: revision{16, 0},
+				modified: revision{main: 16},
+				generations: []generation{
+					{created: revision{main: 14}, ver: 3, revs: []revision{revision{main: 16}}},
+					{},
+				},
+			},
+			map[revision]struct{}{
+				revision{main: 16}: {},
+			},
+		},
+		{
+			17,
+			&keyIndex{
+				key:      []byte("foo"),
+				modified: revision{main: 16},
 				generations: []generation{
 					{},
 				},
@@ -443,18 +464,36 @@ func TestKeyIndexCompactAndKeep(t *testing.T) {
 		},
 	}
 
+	isTombstoneRevFn := func(ki *keyIndex, rev int64) bool {
+		for i := 0; i < len(ki.generations)-1; i++ {
+			g := ki.generations[i]
+
+			if l := len(g.revs); l > 0 && g.revs[l-1].main == rev {
+				return true
+			}
+		}
+		return false
+	}
+
 	// Continuous Compaction and finding Keep
 	ki := newTestKeyIndex()
 	for i, tt := range tests {
+		isTombstone := isTombstoneRevFn(ki, tt.compact)
+
 		am := make(map[revision]struct{})
 		kiclone := cloneKeyIndex(ki)
 		ki.keep(tt.compact, am)
 		if !reflect.DeepEqual(ki, kiclone) {
 			t.Errorf("#%d: ki = %+v, want %+v", i, ki, kiclone)
 		}
-		if !reflect.DeepEqual(am, tt.wam) {
-			t.Errorf("#%d: am = %+v, want %+v", i, am, tt.wam)
+
+		if isTombstone {
+			assert.Equal(t, 0, len(am), "#%d: ki = %d, keep result wants empty because tombstone", i, ki)
+		} else {
+			assert.Equal(t, tt.wam, am,
+				"#%d: ki = %d, compact keep should be equal to keep keep if it's not tombstone", i, ki)
 		}
+
 		am = make(map[revision]struct{})
 		ki.compact(zap.NewExample(), tt.compact, am)
 		if !reflect.DeepEqual(ki, tt.wki) {
@@ -468,7 +507,7 @@ func TestKeyIndexCompactAndKeep(t *testing.T) {
 	// Jump Compaction and finding Keep
 	ki = newTestKeyIndex()
 	for i, tt := range tests {
-		if (i%2 == 0 && i < 6) || (i%2 == 1 && i > 6) {
+		if !isTombstoneRevFn(ki, tt.compact) {
 			am := make(map[revision]struct{})
 			kiclone := cloneKeyIndex(ki)
 			ki.keep(tt.compact, am)
@@ -498,9 +537,14 @@ func TestKeyIndexCompactAndKeep(t *testing.T) {
 		if !reflect.DeepEqual(ki, kiClone) {
 			t.Errorf("#%d: ki = %+v, want %+v", i, ki, kiClone)
 		}
-		if !reflect.DeepEqual(am, tt.wam) {
-			t.Errorf("#%d: am = %+v, want %+v", i, am, tt.wam)
+
+		if isTombstoneRevFn(ki, tt.compact) {
+			assert.Equal(t, 0, len(am), "#%d: ki = %d, keep result wants empty because tombstone", i, ki)
+		} else {
+			assert.Equal(t, tt.wam, am,
+				"#%d: ki = %d, compact keep should be equal to keep keep if it's not tombstone", i, ki)
 		}
+
 		am = make(map[revision]struct{})
 		ki.compact(zap.NewExample(), tt.compact, am)
 		if !reflect.DeepEqual(ki, tt.wki) {
diff --git a/tests/e2e/watch_test.go b/tests/e2e/watch_test.go
index d911736eced..d09347f5bdd 100644
--- a/tests/e2e/watch_test.go
+++ b/tests/e2e/watch_test.go
@@ -25,8 +25,12 @@ import (
 	"testing"
 	"time"
 
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
+
+	"go.etcd.io/etcd/api/v3/etcdserverpb"
 	"go.etcd.io/etcd/api/v3/mvccpb"
+	v3rpc "go.etcd.io/etcd/api/v3/v3rpc/rpctypes"
 	clientv3 "go.etcd.io/etcd/client/v3"
 	"go.etcd.io/etcd/tests/v3/framework/e2e"
 	"golang.org/x/sync/errgroup"
@@ -245,8 +249,7 @@ func continuouslyExecuteGetAll(ctx context.Context, t *testing.T, g *errgroup.Gr
 //   - COMPACT r5
 //   - WATCH rev=r5
 //
-// We should get the DELETE event (r5) followed by the PUT event (r6). However, currently we only
-// get the PUT event with returned revision of r6 (key=k, val=v6).
+// We should get the DELETE event (r5) followed by the PUT event (r6).
 func TestDeleteEventDrop_Issue18089(t *testing.T) {
 	e2e.BeforeTest(t)
 
@@ -299,24 +302,183 @@ func TestDeleteEventDrop_Issue18089(t *testing.T) {
 	watchChan := c.Watch(ctx, key, clientv3.WithRev(deleteResp.Header.Revision))
 	select {
 	case watchResp := <-watchChan:
-		// TODO(MadhavJivrajani): update conditions once https://github.com/etcd-io/etcd/issues/18089
-		// is resolved. The existing conditions do not mimic the desired behaviour and are there to
-		// test and reproduce etcd-io/etcd#18089.
-		if len(watchResp.Events) != 1 {
-			t.Fatalf("expected exactly one event in response, got: %d", len(watchResp.Events))
-		}
-		if watchResp.Events[0].Type != mvccpb.PUT {
-			t.Fatalf("unexpected event type, expected: %s, got: %s", mvccpb.PUT, watchResp.Events[0].Type)
-		}
-		if string(watchResp.Events[0].Kv.Key) != key {
-			t.Fatalf("unexpected key, expected: %s, got: %s", key, string(watchResp.Events[0].Kv.Key))
-		}
-		if string(watchResp.Events[0].Kv.Value) != v6 {
-			t.Fatalf("unexpected valye, expected: %s, got: %s", v6, string(watchResp.Events[0].Kv.Value))
-		}
+		require.Len(t, watchResp.Events, 2)
+
+		require.Equal(t, mvccpb.DELETE, watchResp.Events[0].Type)
+		deletedKey := string(watchResp.Events[0].Kv.Key)
+		require.Equal(t, key, deletedKey)
+
+		require.Equal(t, mvccpb.PUT, watchResp.Events[1].Type)
+
+		updatedKey := string(watchResp.Events[1].Kv.Key)
+		require.Equal(t, key, updatedKey)
+
+		require.Equal(t, v6, string(watchResp.Events[1].Kv.Value))
 	case <-time.After(100 * time.Millisecond):
 		// we care only about the first response, but have an
 		// escape hatch in case the watch response is delayed.
 		t.Fatal("timed out getting watch response")
 	}
 }
+
+func TestStartWatcherFromCompactedRevision(t *testing.T) {
+	t.Run("compaction on tombstone revision", func(t *testing.T) {
+		testStartWatcherFromCompactedRevision(t, true)
+	})
+	t.Run("compaction on normal revision", func(t *testing.T) {
+		testStartWatcherFromCompactedRevision(t, false)
+	})
+}
+
+func testStartWatcherFromCompactedRevision(t *testing.T, performCompactOnTombstone bool) {
+	e2e.BeforeTest(t)
+
+	cfg := e2e.EtcdProcessClusterConfig{
+		ClusterSize:     1,
+		IsClientAutoTLS: true,
+		ClientTLS:       e2e.ClientTLS,
+	}
+
+	clus, err := e2e.NewEtcdProcessCluster(t, &cfg)
+	require.NoError(t, err)
+	defer clus.Close()
+
+	c := newClient(t, clus.EndpointsGRPC(), cfg.ClientTLS, cfg.IsClientAutoTLS)
+	defer c.Close()
+
+	ctx := context.Background()
+	key := "foo"
+	totalRev := 100
+
+	type valueEvent struct {
+		value string
+		typ   mvccpb.Event_EventType
+	}
+
+	var (
+		// requestedValues records all requested change
+		requestedValues = make([]valueEvent, 0)
+		// revisionChan sends each compacted revision via this channel
+		compactionRevChan = make(chan int64)
+		// compactionStep means that client performs a compaction on every 7 operations
+		compactionStep = 7
+	)
+
+	// This goroutine will submit changes on $key $totalRev times. It will
+	// perform compaction after every $compactedAfterChanges changes.
+	// Except for first time, the watcher always receives the compacted
+	// revision as start.
+	go func() {
+		defer close(compactionRevChan)
+
+		lastRevision := int64(1)
+
+		compactionRevChan <- lastRevision
+		for vi := 1; vi <= totalRev; vi++ {
+			var respHeader *etcdserverpb.ResponseHeader
+
+			if vi%compactionStep == 0 && performCompactOnTombstone {
+				t.Logf("DELETE key=%s", key)
+
+				resp, derr := c.KV.Delete(ctx, key)
+				require.NoError(t, derr)
+				respHeader = resp.Header
+
+				requestedValues = append(requestedValues, valueEvent{value: "", typ: mvccpb.DELETE})
+			} else {
+				value := fmt.Sprintf("%d", vi)
+
+				t.Logf("PUT key=%s, val=%s", key, value)
+				resp, perr := c.KV.Put(ctx, key, value)
+				require.NoError(t, perr)
+				respHeader = resp.Header
+
+				requestedValues = append(requestedValues, valueEvent{value: value, typ: mvccpb.PUT})
+			}
+
+			lastRevision = respHeader.Revision
+
+			if vi%compactionStep == 0 {
+				compactionRevChan <- lastRevision
+
+				t.Logf("COMPACT rev=%d", lastRevision)
+				_, err = c.KV.Compact(ctx, lastRevision, clientv3.WithCompactPhysical())
+				require.NoError(t, err)
+			}
+		}
+	}()
+
+	receivedEvents := make([]*clientv3.Event, 0)
+
+	fromCompactedRev := false
+	for fromRev := range compactionRevChan {
+		watchChan := c.Watch(ctx, key, clientv3.WithRev(fromRev))
+
+		prevEventCount := len(receivedEvents)
+
+		// firstReceived represents this is first watch response.
+		// Just in case that ETCD sends event one by one.
+		firstReceived := true
+
+		t.Logf("Start to watch key %s starting from revision %d", key, fromRev)
+	watchLoop:
+		for {
+			currentEventCount := len(receivedEvents)
+			if currentEventCount-prevEventCount == compactionStep || currentEventCount == totalRev {
+				break
+			}
+
+			select {
+			case watchResp := <-watchChan:
+				t.Logf("Receive the number of events: %d", len(watchResp.Events))
+				for i := range watchResp.Events {
+					ev := watchResp.Events[i]
+
+					// If the $fromRev is the compacted revision,
+					// the first event should be the same as the last event receives in last watch response.
+					if firstReceived && fromCompactedRev {
+						firstReceived = false
+
+						last := receivedEvents[prevEventCount-1]
+
+						assert.Equal(t, last.Type, ev.Type,
+							"last received event type %s, but got event type %s", last.Type, ev.Type)
+						assert.Equal(t, string(last.Kv.Key), string(ev.Kv.Key),
+							"last received event key %s, but got event key %s", string(last.Kv.Key), string(ev.Kv.Key))
+						assert.Equal(t, string(last.Kv.Value), string(ev.Kv.Value),
+							"last received event value %s, but got event value %s", string(last.Kv.Value), string(ev.Kv.Value))
+						continue
+					}
+					receivedEvents = append(receivedEvents, ev)
+				}
+
+				if len(watchResp.Events) == 0 {
+					require.Equal(t, v3rpc.ErrCompacted, watchResp.Err())
+					break watchLoop
+				}
+
+			case <-time.After(10 * time.Second):
+				t.Fatal("timed out getting watch response")
+			}
+		}
+
+		fromCompactedRev = true
+	}
+
+	t.Logf("Received total number of events: %d", len(receivedEvents))
+	require.Len(t, requestedValues, totalRev)
+	require.Len(t, receivedEvents, totalRev, "should receive %d events", totalRev)
+	for idx, expected := range requestedValues {
+		ev := receivedEvents[idx]
+
+		require.Equal(t, expected.typ, ev.Type, "#%d expected event %s", idx, expected.typ)
+
+		updatedKey := string(ev.Kv.Key)
+
+		require.Equal(t, key, updatedKey)
+		if expected.typ == mvccpb.PUT {
+			updatedValue := string(ev.Kv.Value)
+			require.Equal(t, expected.value, updatedValue)
+		}
+	}
+}