diff --git a/blob/fileblob/fileblob.go b/blob/fileblob/fileblob.go
index 245d30e0bc..c604071163 100644
--- a/blob/fileblob/fileblob.go
+++ b/blob/fileblob/fileblob.go
@@ -536,11 +536,13 @@ func (b *bucket) ListPaged(ctx context.Context, opts *driver.ListOptions) (*driv
 			return nil
 		}
 		// If we've already got a full page of results, set NextPageToken and stop.
-		// Unless the current object is a directory, in which case there may
-		// still be objects coming that are alphabetically before it (since
-		// we appended the delimiter). In that case, keep going; we'll trim the
-		// extra entries (if any) before returning.
-		if len(result.Objects) == pageSize && !obj.IsDir {
+		// We can only stop if this object is guaranteed to belong after the page,
+		// i.e. it sorts after the last object in it. That isn't always the case:
+		// adding the delimiter can make an object sort before one we've already
+		// added (e.g., the file "a-b" sorts before the "directory" "a/", but is
+		// visited after it), so keep going in that case; we'll trim the extra
+		// entries before returning.
+		if len(result.Objects) == pageSize && !obj.IsDir && obj.Key > result.Objects[pageSize-1].Key {
 			result.NextPageToken = []byte(result.Objects[pageSize-1].Key)
 			return io.EOF
 		}
diff --git a/blob/fileblob/fileblob_test.go b/blob/fileblob/fileblob_test.go
index 12469e0883..db12590f1e 100644
--- a/blob/fileblob/fileblob_test.go
+++ b/blob/fileblob/fileblob_test.go
@@ -25,6 +25,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"slices"
 	"strings"
 	"testing"
 
@@ -684,3 +685,66 @@ func TestSkipMetadata(t *testing.T) {
 		}
 	}
 }
+
+// TestListPagedSortsBeforeDirectory checks that paging doesn't skip keys when a
+// file sorts before the "directory" key generated for its sibling directory.
+// For example, "dir-file" sorts before "dir/" because '-' < '/', but the walk
+// visits "dir/" first, so the file can show up after the page is already full.
+func TestListPagedSortsBeforeDirectory(t *testing.T) {
+	tests := []struct {
+		name string
+		keys []string
+	}{
+		{"one sibling", []string{"dir/a", "dir/b", "dir-file", "f"}},
+		{"several siblings", []string{"a/b", "a-c", "a-d"}},
+		{"nested", []string{"x/y/z", "x-w", "x-v"}},
+	}
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			ctx := context.Background()
+			b, err := OpenBucket(t.TempDir(), nil)
+			if err != nil {
+				t.Fatal(err)
+			}
+			defer closeWithErrorCheck(t, b)
+			for _, key := range test.keys {
+				if err := b.WriteAll(ctx, key, []byte("hello"), nil); err != nil {
+					t.Fatal(err)
+				}
+			}
+			opts := &blob.ListOptions{Delimiter: "/"}
+
+			// An unpaged list gives the keys in the order they should appear.
+			var want []string
+			iter := b.List(opts)
+			for {
+				obj, err := iter.Next(ctx)
+				if err == io.EOF {
+					break
+				}
+				if err != nil {
+					t.Fatal(err)
+				}
+				want = append(want, obj.Key)
+			}
+
+			// Paging must not change the set of keys, or their order.
+			for pageSize := 1; pageSize <= len(test.keys); pageSize++ {
+				var got []string
+				for token := blob.FirstPageToken; token != nil; {
+					objs, next, err := b.ListPage(ctx, token, pageSize, opts)
+					if err != nil {
+						t.Fatal(err)
+					}
+					for _, obj := range objs {
+						got = append(got, obj.Key)
+					}
+					token = next
+				}
+				if !slices.Equal(got, want) {
+					t.Errorf("pageSize %d: got %v, want %v", pageSize, got, want)
+				}
+			}
+		})
+	}
+}