diff --git a/internal/compiler/output_columns.go b/internal/compiler/output_columns.go
index dbdbe252b3..f123fe8fe7 100644
--- a/internal/compiler/output_columns.go
+++ b/internal/compiler/output_columns.go
@@ -132,33 +132,18 @@ func (c *Compiler) outputColumns(qc *QueryCatalog, node ast.Node) ([]*Column, er
 			if res.Name != nil {
 				name = *res.Name
 			}
-			switch n.Val.(type) {
-			case *ast.String:
-				cols = append(cols, &Column{Name: name, DataType: "text", NotNull: true})
-			case *ast.Integer:
-				cols = append(cols, &Column{Name: name, DataType: "int", NotNull: true})
-			case *ast.Float:
-				cols = append(cols, &Column{Name: name, DataType: "float", NotNull: true})
-			case *ast.Boolean:
-				cols = append(cols, &Column{Name: name, DataType: "bool", NotNull: true})
-			default:
-				cols = append(cols, &Column{Name: name, DataType: "any", NotNull: false})
+			col := convertAConstToColumn(n, name)
+			if col.DataType == "null" {
+				col.DataType = "any"
 			}
+			cols = append(cols, col)
 
 		case *ast.A_Expr:
 			name := ""
 			if res.Name != nil {
 				name = *res.Name
 			}
-			switch op := astutils.Join(n.Name, ""); {
-			case lang.IsComparisonOperator(op):
-				// TODO: Generate a name for these operations
-				cols = append(cols, &Column{Name: name, DataType: "bool", NotNull: true})
-			case lang.IsMathematicalOperator(op):
-				cols = append(cols, &Column{Name: name, DataType: "int", NotNull: true})
-			default:
-				cols = append(cols, &Column{Name: name, DataType: "any", NotNull: false})
-			}
+			cols = append(cols, convertAExprToColumn(n, name))
 
 		case *ast.BoolExpr:
 			name := ""
@@ -183,44 +168,70 @@ func (c *Compiler) outputColumns(qc *QueryCatalog, node ast.Node) ([]*Column, er
 			cols = append(cols, &Column{Name: name, DataType: "bool", NotNull: notNull})
 
 		case *ast.CaseExpr:
-			name := ""
+			var name string
 			if res.Name != nil {
 				name = *res.Name
 			}
-			// TODO: The TypeCase and A_Const code has been copied from below. Instead, we
-			// need a recurse function to get the type of a node.
-			if tc, ok := n.Defresult.(*ast.TypeCast); ok {
-				if tc.TypeName == nil {
-					return nil, errors.New("no type name type cast")
+
+			chosenType := ""
+			chosenNullable := false
+
+			for _, i := range n.Args.Items {
+				cw := i.(*ast.CaseWhen)
+				col, err := convertCaseExprCondToColumn(cw.Result, &name)
+				if err != nil {
+					return nil, err
+				}
+				if col.DataType == "null" {
+					// we don't choose type from this column if its value is null, only choose nullability
+					chosenNullable = true
+					continue
 				}
-				name := ""
-				if ref, ok := tc.Arg.(*ast.ColumnRef); ok {
-					name = astutils.Join(ref.Fields, "_")
+				if col.DataType != chosenType {
+					if chosenType == "" {
+						chosenType = col.DataType
+					} else {
+						chosenType = "any"
+					}
 				}
-				if res.Name != nil {
-					name = *res.Name
+				if !col.NotNull {
+					chosenNullable = true
 				}
-				// TODO Validate column names
-				col := toColumn(tc.TypeName)
-				col.Name = name
-				cols = append(cols, col)
-			} else if aconst, ok := n.Defresult.(*ast.A_Const); ok {
-				switch aconst.Val.(type) {
-				case *ast.String:
-					cols = append(cols, &Column{Name: name, DataType: "text", NotNull: true})
-				case *ast.Integer:
-					cols = append(cols, &Column{Name: name, DataType: "int", NotNull: true})
-				case *ast.Float:
-					cols = append(cols, &Column{Name: name, DataType: "float", NotNull: true})
-				case *ast.Boolean:
-					cols = append(cols, &Column{Name: name, DataType: "bool", NotNull: true})
-				default:
-					cols = append(cols, &Column{Name: name, DataType: "any", NotNull: false})
+			}
+
+			var defaultCol *Column
+			if n.Defresult.Pos() != 0 {
+				defaultCol, err = convertCaseExprCondToColumn(n.Defresult, &name)
+				if err != nil {
+					return nil, err
 				}
 			} else {
-				cols = append(cols, &Column{Name: name, DataType: "any", NotNull: false})
+				defaultCol = &Column{Name: name, DataType: "null", NotNull: false}
+			}
+
+			if defaultCol.DataType == "null" {
+				// we don't choose type from this column if its value is null, only choose nullability
+				chosenNullable = true
+			} else {
+				if defaultCol.DataType != chosenType {
+					if chosenType == "" {
+						chosenType = defaultCol.DataType
+					} else {
+						chosenType = "any"
+					}
+				}
+				if !defaultCol.NotNull {
+					chosenNullable = true
+				}
+			}
+
+			if chosenType == "" {
+				chosenType = "any"
 			}
 
+			chosenColumn := &Column{Name: name, DataType: chosenType, NotNull: !chosenNullable}
+			cols = append(cols, chosenColumn)
+
 		case *ast.CoalesceExpr:
 			name := "coalesce"
 			if res.Name != nil {
@@ -256,7 +267,6 @@ func (c *Compiler) outputColumns(qc *QueryCatalog, node ast.Node) ([]*Column, er
 
 		case *ast.ColumnRef:
 			if hasStarRef(n) {
-
 				// add a column with a reference to an embedded table
 				if embed, ok := qc.embeds.Find(n); ok {
 					cols = append(cols, &Column{
@@ -366,6 +376,11 @@ func (c *Compiler) outputColumns(qc *QueryCatalog, node ast.Node) ([]*Column, er
 					col.NotNull = false
 				}
 			}
+			if expr, ok := n.Arg.(*ast.A_Expr); ok {
+				if op := astutils.Join(expr.Name, ""); lang.IsJSONOperator(op) {
+					col.NotNull = false
+				}
+			}
 			cols = append(cols, col)
 
 		case *ast.SelectStmt:
@@ -764,3 +779,74 @@ func findColumnForRef(ref *ast.ColumnRef, tables []*Table, targetList *ast.List)
 
 	return nil
 }
+
+func convertCaseExprCondToColumn(n ast.Node, resTargetName *string) (*Column, error) {
+	var col *Column
+	name := ""
+	if resTargetName != nil {
+		name = *resTargetName
+	}
+
+	if tc, ok := n.(*ast.TypeCast); ok {
+		if tc.TypeName == nil {
+			return nil, errors.New("no type name type cast")
+		}
+		if ref, ok := tc.Arg.(*ast.ColumnRef); ok {
+			name = astutils.Join(ref.Fields, "_")
+		}
+		// TODO Validate column names
+		col = toColumn(tc.TypeName)
+
+		if x, ok := tc.Arg.(*ast.A_Const); ok {
+			if _, ok := x.Val.(*ast.Null); ok {
+				col.NotNull = false
+			}
+		}
+		col.Name = name
+
+	} else if aconst, ok := n.(*ast.A_Const); ok {
+		col = convertAConstToColumn(aconst, name)
+	} else if aexpr, ok := n.(*ast.A_Expr); ok {
+		col = convertAExprToColumn(aexpr, name)
+	} else {
+		col = &Column{Name: name, DataType: "any", NotNull: false}
+	}
+
+	return col, nil
+}
+
+func convertAExprToColumn(aexpr *ast.A_Expr, name string) *Column {
+	var col *Column
+	switch op := astutils.Join(aexpr.Name, ""); {
+	case lang.IsComparisonOperator(op):
+		// TODO: Generate a name for these operations
+		col = &Column{Name: name, DataType: "bool", NotNull: true}
+	case lang.IsMathematicalOperator(op):
+		col = &Column{Name: name, DataType: "int", NotNull: true}
+	case lang.IsJSONOperator(op) && lang.IsJSONResultAsText(op):
+		col = &Column{Name: name, DataType: "text", NotNull: false}
+	default:
+		col = &Column{Name: name, DataType: "any", NotNull: false}
+	}
+
+	return col
+}
+
+func convertAConstToColumn(aconst *ast.A_Const, name string) (*Column) {
+	var col *Column
+	switch aconst.Val.(type) {
+	case *ast.String:
+		col = &Column{Name: name, DataType: "text", NotNull: true}
+	case *ast.Integer:
+		col = &Column{Name: name, DataType: "int", NotNull: true}
+	case *ast.Float:
+		col = &Column{Name: name, DataType: "float", NotNull: true}
+	case *ast.Boolean:
+		col = &Column{Name: name, DataType: "bool", NotNull: true}
+	case *ast.Null:
+		col = &Column{Name: name, DataType: "null", NotNull: false}
+	default:
+		col = &Column{Name: name, DataType: "any", NotNull: false}
+	}
+	return col
+}
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/issue.md b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/issue.md
new file mode 100644
index 0000000000..eb8c6145f3
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/issue.md
@@ -0,0 +1 @@
+https://github.com/sqlc-dev/sqlc/issues/3710
\ No newline at end of file
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/exec.json b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/exec.json
new file mode 100644
index 0000000000..2e996ca79d
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/exec.json
@@ -0,0 +1,3 @@
+{
+  "contexts": ["base"]
+}
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/db.go b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/db.go
new file mode 100644
index 0000000000..69ef001548
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/db.go
@@ -0,0 +1,32 @@
+// Code generated by sqlc. DO NOT EDIT.
+// versions:
+//   sqlc v1.27.0
+
+package querytest
+
+import (
+	"context"
+
+	"github.com/jackc/pgx/v5"
+	"github.com/jackc/pgx/v5/pgconn"
+)
+
+type DBTX interface {
+	Exec(context.Context, string, ...interface{}) (pgconn.CommandTag, error)
+	Query(context.Context, string, ...interface{}) (pgx.Rows, error)
+	QueryRow(context.Context, string, ...interface{}) pgx.Row
+}
+
+func New(db DBTX) *Queries {
+	return &Queries{db: db}
+}
+
+type Queries struct {
+	db DBTX
+}
+
+func (q *Queries) WithTx(tx pgx.Tx) *Queries {
+	return &Queries{
+		db: tx,
+	}
+}
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/models.go b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/models.go
new file mode 100644
index 0000000000..c0841a0eb9
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/models.go
@@ -0,0 +1,10 @@
+// Code generated by sqlc. DO NOT EDIT.
+// versions:
+//   sqlc v1.27.0
+
+package querytest
+
+type Mytable struct {
+	ID     int64  `json:"id"`
+	Myjson []byte `json:"myjson"`
+}
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/query.sql.go b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/query.sql.go
new file mode 100644
index 0000000000..be9edd4c42
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/go/query.sql.go
@@ -0,0 +1,418 @@
+// Code generated by sqlc. DO NOT EDIT.
+// versions:
+//   sqlc v1.27.0
+// source: query.sql
+
+package querytest
+
+import (
+	"context"
+
+	"github.com/jackc/pgx/v5/pgtype"
+)
+
+const getNullable1 = `-- name: GetNullable1 :many
+SELECT null::text
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable1(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable1)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2 = `-- name: GetNullable2 :many
+SELECT CASE
+    WHEN id = 1 THEN id::int
+    WHEN id = 2 THEN null
+    WHEN id = 3 THEN 8.5
+    WHEN id = 4 THEN 7
+    ELSE '2'
+END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable2(ctx context.Context) ([]interface{}, error) {
+	rows, err := q.db.Query(ctx, getNullable2)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []interface{}
+	for rows.Next() {
+		var column_1 interface{}
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2A = `-- name: GetNullable2A :many
+SELECT CASE
+    WHEN id = 1 THEN id::int
+    WHEN id = 2 THEN null
+    WHEN id = 3 THEN 8.5
+    ELSE 7
+END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable2A(ctx context.Context) ([]interface{}, error) {
+	rows, err := q.db.Query(ctx, getNullable2A)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []interface{}
+	for rows.Next() {
+		var column_1 interface{}
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2B = `-- name: GetNullable2B :many
+SELECT CASE
+    WHEN id = 1 THEN id::float
+    WHEN id = 2 THEN null
+    ELSE 7
+END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable2B(ctx context.Context) ([]interface{}, error) {
+	rows, err := q.db.Query(ctx, getNullable2B)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []interface{}
+	for rows.Next() {
+		var column_1 interface{}
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2C = `-- name: GetNullable2C :many
+SELECT CASE
+    WHEN id = 1 THEN true
+    ELSE null
+    END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable2C(ctx context.Context) ([]pgtype.Bool, error) {
+	rows, err := q.db.Query(ctx, getNullable2C)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Bool
+	for rows.Next() {
+		var column_1 pgtype.Bool
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2D = `-- name: GetNullable2D :many
+SELECT CASE
+    WHEN id = 2 THEN mt.myjson->'thing1'->>'thing2'
+    ELSE null
+    END
+FROM "mytable" mt
+`
+
+func (q *Queries) GetNullable2D(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable2D)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2E = `-- name: GetNullable2E :many
+SELECT CASE
+    WHEN id = 2 THEN mt.myjson->'thing1'->'thing2'
+    WHEN id = 3 THEN mt.myjson->'thing1'
+    ELSE null
+    END
+FROM "mytable" mt
+`
+
+func (q *Queries) GetNullable2E(ctx context.Context) ([]interface{}, error) {
+	rows, err := q.db.Query(ctx, getNullable2E)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []interface{}
+	for rows.Next() {
+		var column_1 interface{}
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2F = `-- name: GetNullable2F :many
+SELECT CASE
+    WHEN id = 2 THEN null
+    ELSE 7 - id
+END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable2F(ctx context.Context) ([]pgtype.Int4, error) {
+	rows, err := q.db.Query(ctx, getNullable2F)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Int4
+	for rows.Next() {
+		var column_1 pgtype.Int4
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable2G = `-- name: GetNullable2G :many
+SELECT CASE
+    WHEN id = 2 THEN null
+    ELSE null
+END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable2G(ctx context.Context) ([]interface{}, error) {
+	rows, err := q.db.Query(ctx, getNullable2G)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []interface{}
+	for rows.Next() {
+		var column_1 interface{}
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable3 = `-- name: GetNullable3 :many
+SELECT CASE WHEN true THEN 'hello'::text ELSE null END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable3(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable3)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable3B = `-- name: GetNullable3B :many
+SELECT CASE WHEN true THEN 'hello'::text ELSE null::text END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable3B(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable3B)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable4 = `-- name: GetNullable4 :many
+SELECT CASE WHEN true THEN 'hello'::text END
+FROM "mytable"
+`
+
+func (q *Queries) GetNullable4(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable4)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable5 = `-- name: GetNullable5 :many
+SELECT (mt.myjson->'thing1'->'thing2')::text
+FROM "mytable" mt
+`
+
+func (q *Queries) GetNullable5(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable5)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable6 = `-- name: GetNullable6 :many
+SELECT mt.myjson->'thing1'->>'thing2'
+FROM "mytable" mt
+`
+
+func (q *Queries) GetNullable6(ctx context.Context) ([]pgtype.Text, error) {
+	rows, err := q.db.Query(ctx, getNullable6)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []pgtype.Text
+	for rows.Next() {
+		var column_1 pgtype.Text
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getNullable7 = `-- name: GetNullable7 :many
+SELECT mt.myjson->'thing1'->'thing2'
+FROM "mytable" mt
+`
+
+func (q *Queries) GetNullable7(ctx context.Context) ([]interface{}, error) {
+	rows, err := q.db.Query(ctx, getNullable7)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []interface{}
+	for rows.Next() {
+		var column_1 interface{}
+		if err := rows.Scan(&column_1); err != nil {
+			return nil, err
+		}
+		items = append(items, column_1)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/query.sql b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/query.sql
new file mode 100644
index 0000000000..c5dccf6312
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/query.sql
@@ -0,0 +1,90 @@
+-- name: GetNullable1 :many
+SELECT null::text
+FROM "mytable";
+
+-- name: GetNullable2 :many
+SELECT CASE
+    WHEN id = 1 THEN id::int
+    WHEN id = 2 THEN null
+    WHEN id = 3 THEN 8.5
+    WHEN id = 4 THEN 7
+    ELSE '2'
+END
+FROM "mytable";
+
+-- name: GetNullable3 :many
+SELECT CASE WHEN true THEN 'hello'::text ELSE null END
+FROM "mytable";
+
+-- name: GetNullable3B :many
+SELECT CASE WHEN true THEN 'hello'::text ELSE null::text END
+FROM "mytable";
+
+-- name: GetNullable4 :many
+SELECT CASE WHEN true THEN 'hello'::text END
+FROM "mytable";
+
+-- name: GetNullable5 :many
+SELECT (mt.myjson->'thing1'->'thing2')::text
+FROM "mytable" mt;
+
+-- name: GetNullable6 :many
+SELECT mt.myjson->'thing1'->>'thing2'
+FROM "mytable" mt;
+
+-- name: GetNullable7 :many
+SELECT mt.myjson->'thing1'->'thing2'
+FROM "mytable" mt;
+
+-- name: GetNullable2A :many
+SELECT CASE
+    WHEN id = 1 THEN id::int
+    WHEN id = 2 THEN null
+    WHEN id = 3 THEN 8.5
+    ELSE 7
+END
+FROM "mytable";
+
+-- name: GetNullable2B :many
+SELECT CASE
+    WHEN id = 1 THEN id::float
+    WHEN id = 2 THEN null
+    ELSE 7
+END
+FROM "mytable";
+
+-- name: GetNullable2C :many
+SELECT CASE
+    WHEN id = 1 THEN true
+    ELSE null
+    END
+FROM "mytable";
+
+-- name: GetNullable2D :many
+SELECT CASE
+    WHEN id = 2 THEN mt.myjson->'thing1'->>'thing2'
+    ELSE null
+    END
+FROM "mytable" mt;
+
+-- name: GetNullable2E :many
+SELECT CASE
+    WHEN id = 2 THEN mt.myjson->'thing1'->'thing2'
+    WHEN id = 3 THEN mt.myjson->'thing1'
+    ELSE null
+    END
+FROM "mytable" mt;
+
+-- name: GetNullable2F :many
+SELECT CASE
+    WHEN id = 2 THEN null
+    ELSE 7 - id
+END
+FROM "mytable";
+
+-- name: GetNullable2G :many
+SELECT CASE
+    WHEN id = 2 THEN null
+    ELSE null
+END
+FROM "mytable";
\ No newline at end of file
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/schema.sql b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/schema.sql
new file mode 100644
index 0000000000..81cad60b92
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/schema.sql
@@ -0,0 +1,8 @@
+CREATE TABLE "mytable" (
+    id                BIGSERIAL   NOT NULL PRIMARY KEY,
+    myjson             JSONB       NOT NULL
+);
+
+insert into mytable (myjson) values
+    ('{}'),
+    ('{"thing1": {"thing2": "thing3"}}');
\ No newline at end of file
diff --git a/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/sqlc.yaml b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/sqlc.yaml
new file mode 100644
index 0000000000..3065f606c0
--- /dev/null
+++ b/internal/endtoend/testdata/json_traversal_as_select_expr_with_type_cast/postgresql/pgx/sqlc.yaml
@@ -0,0 +1,11 @@
+version: "2"
+sql:
+  - engine: "postgresql"
+    queries: "query.sql"
+    schema: "schema.sql"
+    gen:
+      go:
+        package: "querytest"
+        out: "go"
+        sql_package: "pgx/v5"
+        emit_json_tags: true
\ No newline at end of file
diff --git a/internal/sql/lang/operator.go b/internal/sql/lang/operator.go
index cd5ef50e38..12cc661c31 100644
--- a/internal/sql/lang/operator.go
+++ b/internal/sql/lang/operator.go
@@ -41,3 +41,25 @@ func IsMathematicalOperator(s string) bool {
 	}
 	return true
 }
+
+func IsJSONOperator(s string) bool {
+	switch s {
+	case "->":
+	case "->>":
+	case "#>":
+	case "#>>":
+	default:
+		return false
+	}
+	return true
+}
+
+func IsJSONResultAsText(s string) bool {
+	switch s {
+	case "->>":
+	case "#>>":
+	default:
+		return false
+	}
+	return true
+}