diff --git a/internal/datastore/postgres/common/bulk.go b/internal/datastore/postgres/common/bulk.go
index 9ba4ebea90..51de5a8073 100644
--- a/internal/datastore/postgres/common/bulk.go
+++ b/internal/datastore/postgres/common/bulk.go
@@ -2,7 +2,6 @@ package common
 
 import (
 	"context"
-	"database/sql"
 
 	"github.com/jackc/pgx/v5"
 
@@ -29,11 +28,10 @@ func (tg *tupleSourceAdapter) Next() bool {
 
 // Values returns the values for the current row.
 func (tg *tupleSourceAdapter) Values() ([]any, error) {
-	var caveatName sql.NullString
+	var caveatName string
 	var caveatContext map[string]any
 	if tg.current.Caveat != nil {
-		caveatName.String = tg.current.Caveat.CaveatName
-		caveatName.Valid = true
+		caveatName = tg.current.Caveat.CaveatName
 		caveatContext = tg.current.Caveat.Context.AsMap()
 	}
 
diff --git a/internal/datastore/postgres/readwrite.go b/internal/datastore/postgres/readwrite.go
index a8f689a921..dd34218c26 100644
--- a/internal/datastore/postgres/readwrite.go
+++ b/internal/datastore/postgres/readwrite.go
@@ -725,9 +725,7 @@ func exactRelationshipDifferentCaveatClause(r *core.RelationTuple) sq.And {
 			colUsersetRelation:  r.Subject.Relation,
 		},
 		sq.Or{
-			sq.NotEq{
-				colCaveatContextName: caveatName,
-			},
+			sq.Expr(fmt.Sprintf(`%s IS DISTINCT FROM ?`, colCaveatContextName), caveatName),
 			sq.NotEq{
 				colCaveatContext: caveatContext,
 			},
diff --git a/pkg/datastore/test/bulk.go b/pkg/datastore/test/bulk.go
index a5fa31c576..1e20e3eb19 100644
--- a/pkg/datastore/test/bulk.go
+++ b/pkg/datastore/test/bulk.go
@@ -119,6 +119,79 @@ func BulkUploadAlreadyExistsSameCallErrorTest(t *testing.T, tester DatastoreTest
 	grpcutil.RequireStatus(t, codes.AlreadyExists, err)
 }
 
+func BulkUploadEditCaveat(t *testing.T, tester DatastoreTester) {
+	tc := 10
+	require := require.New(t)
+	ctx := context.Background()
+
+	rawDS, err := tester.New(0, veryLargeGCInterval, veryLargeGCWindow, 1)
+	require.NoError(err)
+
+	ds, _ := testfixtures.StandardDatastoreWithSchema(rawDS, require)
+	bulkSource := testfixtures.NewBulkTupleGenerator(
+		testfixtures.DocumentNS.Name,
+		"caveated_viewer",
+		testfixtures.UserNS.Name,
+		tc,
+		t,
+	)
+
+	lastRevision, err := ds.ReadWriteTx(ctx, func(ctx context.Context, rwt datastore.ReadWriteTransaction) error {
+		loaded, err := rwt.BulkLoad(ctx, bulkSource)
+		require.NoError(err)
+		require.Equal(uint64(tc), loaded)
+		return err
+	})
+	require.NoError(err)
+
+	iter, err := ds.SnapshotReader(lastRevision).QueryRelationships(ctx, datastore.RelationshipsFilter{
+		OptionalResourceType: testfixtures.DocumentNS.Name,
+	})
+	require.NoError(err)
+	defer iter.Close()
+
+	updates := make([]*core.RelationTupleUpdate, 0, tc)
+
+	for found := iter.Next(); found != nil; found = iter.Next() {
+		updates = append(updates, &core.RelationTupleUpdate{
+			Operation: core.RelationTupleUpdate_TOUCH,
+			Tuple: &core.RelationTuple{
+				ResourceAndRelation: found.ResourceAndRelation,
+				Subject:             found.Subject,
+				Caveat: &core.ContextualizedCaveat{
+					CaveatName: testfixtures.CaveatDef.Name,
+					Context:    nil,
+				},
+			},
+		})
+	}
+
+	require.Equal(tc, len(updates))
+
+	lastRevision, err = ds.ReadWriteTx(ctx, func(ctx context.Context, rwt datastore.ReadWriteTransaction) error {
+		err := rwt.WriteRelationships(ctx, updates)
+		require.NoError(err)
+		return err
+	})
+	require.NoError(err)
+
+	iter, err = ds.SnapshotReader(lastRevision).QueryRelationships(ctx, datastore.RelationshipsFilter{
+		OptionalResourceType: testfixtures.DocumentNS.Name,
+	})
+	require.NoError(err)
+	defer iter.Close()
+
+	foundChanged := 0
+
+	for found := iter.Next(); found != nil; found = iter.Next() {
+		require.NotNil(found.Caveat)
+		require.NotEmpty(found.Caveat.CaveatName)
+		foundChanged++
+	}
+
+	require.Equal(tc, foundChanged)
+}
+
 func BulkUploadAlreadyExistsErrorTest(t *testing.T, tester DatastoreTester) {
 	require := require.New(t)
 	ctx := context.Background()
diff --git a/pkg/datastore/test/datastore.go b/pkg/datastore/test/datastore.go
index a38751cc33..4cc10ef019 100644
--- a/pkg/datastore/test/datastore.go
+++ b/pkg/datastore/test/datastore.go
@@ -140,6 +140,7 @@ func AllWithExceptions(t *testing.T, tester DatastoreTester, except Categories)
 	t.Run("TestBulkUploadErrors", func(t *testing.T) { BulkUploadErrorsTest(t, tester) })
 	t.Run("TestBulkUploadAlreadyExistsError", func(t *testing.T) { BulkUploadAlreadyExistsErrorTest(t, tester) })
 	t.Run("TestBulkUploadAlreadyExistsSameCallError", func(t *testing.T) { BulkUploadAlreadyExistsSameCallErrorTest(t, tester) })
+	t.Run("BulkUploadEditCaveat", func(t *testing.T) { BulkUploadEditCaveat(t, tester) })
 
 	if !except.Stats() {
 		t.Run("TestStats", func(t *testing.T) { StatsTest(t, tester) })