diff --git a/ingest.go b/ingest.go
index 3fe0aae727..23b196d223 100644
--- a/ingest.go
+++ b/ingest.go
@@ -15,6 +15,7 @@ import (
 	"github.com/cockroachdb/pebble/internal/base"
 	"github.com/cockroachdb/pebble/internal/cache"
 	"github.com/cockroachdb/pebble/internal/invariants"
+	"github.com/cockroachdb/pebble/internal/keyspan"
 	"github.com/cockroachdb/pebble/internal/manifest"
 	"github.com/cockroachdb/pebble/internal/overlap"
 	"github.com/cockroachdb/pebble/internal/sstableinternal"
@@ -241,6 +242,10 @@ func ingestLoad1External(
 
 // ingestLoad1 creates the FileMetadata for one file. This file will be owned
 // by this store.
+//
+// lastRangeKey is the last range key from the previous file. It is used to
+// ensure that the range keys defragment cleanly across files. These checks
+// are disabled if disableRangeKeyChecks is true.
 func ingestLoad1(
 	ctx context.Context,
 	opts *Options,
@@ -248,7 +253,9 @@ func ingestLoad1(
 	readable objstorage.Readable,
 	cacheID cache.ID,
 	fileNum base.FileNum,
-) (*fileMetadata, error) {
+	lastRangeKey keyspan.Span,
+	disableRangeKeyChecks bool,
+) (*fileMetadata, keyspan.Span, error) {
 	o := opts.MakeReaderOptions()
 	o.SetInternalCacheOpts(sstableinternal.CacheOptions{
 		Cache:   opts.Cache,
@@ -257,24 +264,24 @@ func ingestLoad1(
 	})
 	r, err := sstable.NewReader(ctx, readable, o)
 	if err != nil {
-		return nil, err
+		return nil, keyspan.Span{}, err
 	}
 	defer r.Close()
 
 	// Avoid ingesting tables with format versions this DB doesn't support.
 	tf, err := r.TableFormat()
 	if err != nil {
-		return nil, err
+		return nil, keyspan.Span{}, err
 	}
 	if tf < fmv.MinTableFormat() || tf > fmv.MaxTableFormat() {
-		return nil, errors.Newf(
+		return nil, keyspan.Span{}, errors.Newf(
 			"pebble: table format %s is not within range supported at DB format major version %d, (%s,%s)",
 			tf, fmv, fmv.MinTableFormat(), fmv.MaxTableFormat(),
 		)
 	}
 	if tf.BlockColumnar() {
 		if _, ok := opts.KeySchemas[r.Properties.KeySchemaName]; !ok {
-			return nil, errors.Newf(
+			return nil, keyspan.Span{}, errors.Newf(
 				"pebble: table uses key schema %q unknown to the database",
 				r.Properties.KeySchemaName)
 		}
@@ -300,52 +307,52 @@ func ingestLoad1(
 	{
 		iter, err := r.NewIter(sstable.NoTransforms, nil /* lower */, nil /* upper */)
 		if err != nil {
-			return nil, err
+			return nil, keyspan.Span{}, err
 		}
 		defer iter.Close()
 		var smallest InternalKey
 		if kv := iter.First(); kv != nil {
 			if err := ingestValidateKey(opts, &kv.K); err != nil {
-				return nil, err
+				return nil, keyspan.Span{}, err
 			}
 			smallest = kv.K.Clone()
 		}
 		if err := iter.Error(); err != nil {
-			return nil, err
+			return nil, keyspan.Span{}, err
 		}
 		if kv := iter.Last(); kv != nil {
 			if err := ingestValidateKey(opts, &kv.K); err != nil {
-				return nil, err
+				return nil, keyspan.Span{}, err
 			}
 			meta.ExtendPointKeyBounds(opts.Comparer.Compare, smallest, kv.K.Clone())
 		}
 		if err := iter.Error(); err != nil {
-			return nil, err
+			return nil, keyspan.Span{}, err
 		}
 	}
 
 	iter, err := r.NewRawRangeDelIter(ctx, sstable.NoFragmentTransforms)
 	if err != nil {
-		return nil, err
+		return nil, keyspan.Span{}, err
 	}
 	if iter != nil {
 		defer iter.Close()
 		var smallest InternalKey
 		if s, err := iter.First(); err != nil {
-			return nil, err
+			return nil, keyspan.Span{}, err
 		} else if s != nil {
 			key := s.SmallestKey()
 			if err := ingestValidateKey(opts, &key); err != nil {
-				return nil, err
+				return nil, keyspan.Span{}, err
 			}
 			smallest = key.Clone()
 		}
 		if s, err := iter.Last(); err != nil {
-			return nil, err
+			return nil, keyspan.Span{}, err
 		} else if s != nil {
 			k := s.SmallestKey()
 			if err := ingestValidateKey(opts, &k); err != nil {
-				return nil, err
+				return nil, keyspan.Span{}, err
 			}
 			largest := s.LargestKey().Clone()
 			meta.ExtendPointKeyBounds(opts.Comparer.Compare, smallest, largest)
@@ -356,45 +363,66 @@ func ingestLoad1(
 	{
 		iter, err := r.NewRawRangeKeyIter(ctx, sstable.NoFragmentTransforms)
 		if err != nil {
-			return nil, err
+			return nil, keyspan.Span{}, err
 		}
 		if iter != nil {
 			defer iter.Close()
 			var smallest InternalKey
 			if s, err := iter.First(); err != nil {
-				return nil, err
+				return nil, keyspan.Span{}, err
 			} else if s != nil {
 				key := s.SmallestKey()
 				if err := ingestValidateKey(opts, &key); err != nil {
-					return nil, err
+					return nil, keyspan.Span{}, err
 				}
 				smallest = key.Clone()
+				// Range keys need some additional validation as we need to ensure they
+				// defragment cleanly with the lastRangeKey from the previous file.
+				if !disableRangeKeyChecks {
+					if lastRangeKey.Valid() {
+						if opts.Comparer.Split.HasSuffix(lastRangeKey.End) && (!opts.Comparer.Equal(lastRangeKey.End, s.Start) ||
+							!keyspan.DefragmentInternal.ShouldDefragment(opts.Comparer.CompareRangeSuffixes, &lastRangeKey, s)) {
+							// The last range key has a suffix, and it doesn't defragment cleanly with this range key.
+							return nil, keyspan.Span{}, errors.AssertionFailedf("pebble: ingest sstable has suffixed range key that won't defragment: %s",
+								opts.Comparer.FormatKey(lastRangeKey.End))
+						}
+					} else if opts.Comparer.Split.HasSuffix(s.Start) {
+						return nil, keyspan.Span{}, errors.Newf("pebble: ingest sstable has suffixed range key start that won't defragment: %s",
+							opts.Comparer.FormatKey(s.Start))
+					}
+				}
 			}
 			if s, err := iter.Last(); err != nil {
-				return nil, err
+				return nil, keyspan.Span{}, err
 			} else if s != nil {
 				k := s.SmallestKey()
 				if err := ingestValidateKey(opts, &k); err != nil {
-					return nil, err
+					return nil, keyspan.Span{}, err
 				}
 				// As range keys are fragmented, the end key of the last range key in
 				// the table provides the upper bound for the table.
 				largest := s.LargestKey().Clone()
 				meta.ExtendRangeKeyBounds(opts.Comparer.Compare, smallest, largest)
+				lastRangeKey = s.Clone()
+			} else {
+				// s == nil.
+				lastRangeKey = keyspan.Span{}
 			}
+		} else {
+			lastRangeKey = keyspan.Span{}
 		}
 	}
 
 	if !meta.HasPointKeys && !meta.HasRangeKeys {
-		return nil, nil
+		return nil, keyspan.Span{}, nil
 	}
 
 	// Sanity check that the various bounds on the file were set consistently.
 	if err := meta.Validate(opts.Comparer.Compare, opts.Comparer.FormatKey); err != nil {
-		return nil, err
+		return nil, keyspan.Span{}, err
 	}
 
-	return meta, nil
+	return meta, lastRangeKey, nil
 }
 
 type ingestLoadResult struct {
@@ -445,6 +473,7 @@ func ingestLoad(
 
 	var result ingestLoadResult
 	result.local = make([]ingestLocalMeta, 0, len(paths))
+	var lastRangeKey keyspan.Span
 	for i := range paths {
 		f, err := opts.FS.Open(paths[i])
 		if err != nil {
@@ -455,7 +484,12 @@ func ingestLoad(
 		if err != nil {
 			return ingestLoadResult{}, err
 		}
-		m, err := ingestLoad1(ctx, opts, fmv, readable, cacheID, localFileNums[i])
+		var m *fileMetadata
+		// NB: we disable range key boundary assertions if we have shared or external files
+		// present in this ingestion. This is because a suffixed range key in a local file
+		// can possibly defragment with a suffixed range key in a shared or external file.
+		disableRangeKeyChecks := len(shared) > 0 || len(external) > 0
+		m, lastRangeKey, err = ingestLoad1(ctx, opts, fmv, readable, cacheID, localFileNums[i], lastRangeKey, disableRangeKeyChecks)
 		if err != nil {
 			return ingestLoadResult{}, err
 		}
@@ -466,6 +500,10 @@ func ingestLoad(
 			})
 		}
 	}
+	if lastRangeKey.Valid() && opts.Comparer.Split.HasSuffix(lastRangeKey.End) {
+		return ingestLoadResult{}, errors.AssertionFailedf("pebble: last ingest sstable has suffixed range key end %s",
+			opts.Comparer.FormatKey(lastRangeKey.End))
+	}
 
 	// Sort the shared files according to level.
 	sort.Sort(sharedByLevel(shared))
diff --git a/internal/base/comparer.go b/internal/base/comparer.go
index 78a7aadd37..c734052de0 100644
--- a/internal/base/comparer.go
+++ b/internal/base/comparer.go
@@ -186,6 +186,13 @@ func (s Split) Prefix(k []byte) []byte {
 	return k[:i:i]
 }
 
+// HasSuffix returns true if the key k has a suffix remaining after
+// Split is called on it. For keys where the entirety of the key is
+// returned by Split, HasSuffix will return false.
+func (s Split) HasSuffix(k []byte) bool {
+	return s(k) < len(k)
+}
+
 // DefaultSplit is a trivial implementation of Split which always returns the
 // full key.
 var DefaultSplit Split = func(key []byte) int { return len(key) }
diff --git a/iterator_histories_test.go b/iterator_histories_test.go
index e22fa18e0b..6b72c1f13d 100644
--- a/iterator_histories_test.go
+++ b/iterator_histories_test.go
@@ -221,6 +221,16 @@ func TestIterHistories(t *testing.T) {
 					}
 				}
 				return buf.String()
+			case "build":
+				if err := runBuildCmd(td, d, d.opts.FS); err != nil {
+					return err.Error()
+				}
+				return ""
+			case "ingest-existing":
+				if err := runIngestCmd(td, d, d.opts.FS); err != nil {
+					return err.Error()
+				}
+				return ""
 			case "ingest":
 				if err := runBuildCmd(td, d, d.opts.FS); err != nil {
 					return err.Error()
diff --git a/open.go b/open.go
index 2610e3451f..94ac3e78ba 100644
--- a/open.go
+++ b/open.go
@@ -24,6 +24,7 @@ import (
 	"github.com/cockroachdb/pebble/internal/cache"
 	"github.com/cockroachdb/pebble/internal/constants"
 	"github.com/cockroachdb/pebble/internal/invariants"
+	"github.com/cockroachdb/pebble/internal/keyspan"
 	"github.com/cockroachdb/pebble/internal/manifest"
 	"github.com/cockroachdb/pebble/internal/manual"
 	"github.com/cockroachdb/pebble/objstorage"
@@ -807,17 +808,23 @@ func (d *DB) replayIngestedFlushable(
 	}
 
 	meta := make([]*fileMetadata, len(fileNums))
+	var lastRangeKey keyspan.Span
 	for i, n := range fileNums {
 		readable, err := d.objProvider.OpenForReading(context.TODO(), fileTypeTable, n, objstorage.OpenOptions{MustExist: true})
 		if err != nil {
 			return nil, errors.Wrap(err, "pebble: error when opening flushable ingest files")
 		}
 		// NB: ingestLoad1 will close readable.
-		meta[i], err = ingestLoad1(context.TODO(), d.opts, d.FormatMajorVersion(), readable, d.cacheID, base.PhysicalTableFileNum(n))
+		meta[i], lastRangeKey, err = ingestLoad1(context.TODO(), d.opts, d.FormatMajorVersion(),
+			readable, d.cacheID, base.PhysicalTableFileNum(n), lastRangeKey, false /* disableRangeKeyChecks */)
 		if err != nil {
 			return nil, errors.Wrap(err, "pebble: error when loading flushable ingest files")
 		}
 	}
+	if lastRangeKey.Valid() && d.opts.Comparer.Split.HasSuffix(lastRangeKey.End) {
+		return nil, errors.AssertionFailedf("pebble: last ingest sstable has suffixed range key end %s",
+			d.opts.Comparer.FormatKey(lastRangeKey.End))
+	}
 
 	numFiles := len(meta)
 	if exciseSpan.Valid() {
diff --git a/testdata/iter_histories/prefix_iteration b/testdata/iter_histories/prefix_iteration
index a5484b51e4..728b504ca8 100644
--- a/testdata/iter_histories/prefix_iteration
+++ b/testdata/iter_histories/prefix_iteration
@@ -140,8 +140,14 @@ ingest ext1
 range-key-set a c@8 @1 bar
 set c@9 c@9
 ----
+pebble: last ingest sstable has suffixed range key end c@8
 
-ingest ext2
+build ext1
+range-key-set a c@8 @1 bar
+set c@9 c@9
+----
+
+build ext2
 range-key-set c@8 e @1 bar
 set c@8 c@8
 set c@7 c@7
@@ -152,6 +158,9 @@ set c@3 c@3
 set c@2 c@2
 ----
 
+ingest-existing ext1 ext2
+----
+
 ingest ext2
 range-key-set y z @1 foo
 set z z
@@ -160,9 +169,9 @@ set z z
 lsm
 ----
 L6:
-  000004:[a#10,RANGEKEYSET-c@8#inf,RANGEKEYSET]
-  000005:[c@8#11,RANGEKEYSET-e#inf,RANGEKEYSET]
-  000006:[y#12,RANGEKEYSET-z#12,SET]
+  000005:[a#10,RANGEKEYSET-c@8#inf,RANGEKEYSET]
+  000006:[c@8#11,RANGEKEYSET-e#inf,RANGEKEYSET]
+  000007:[y#12,RANGEKEYSET-z#12,SET]
 
 
 # The first seek-prefix-ge y@1 converts the iterator from lazy combined iterator