diff --git a/compiler/gengo/gengo.go b/compiler/gengo/gengo.go
index f492124..3d9b977 100644
--- a/compiler/gengo/gengo.go
+++ b/compiler/gengo/gengo.go
@@ -482,8 +482,11 @@ func (g *Generator) emitStmt(stmt ast.Stmt, locals localMap) {
 		if s.ForCond != nil {
 			forExpr = fmt.Sprintf("%q", exprToString(s.ForCond))
 		}
+		// Set VM callback for UDF evaluation during index build
+		g.writeln("dbf.KeyEvalFunc = func(expr string) hbrt.Value { return t.MacroEval(expr) }")
 		g.writeln(fmt.Sprintf("idx.OrderCreate(hbrdd.OrderCreateParams{KeyExpr: _keyExpr, FilePath: _file, ForExpr: %s, Unique: %v, Descending: %v})",
 			forExpr, s.Unique, s.Descending))
+		g.writeln("dbf.KeyEvalFunc = nil")
 		g.indent--
 		g.writeln("}")
 		g.indent--
diff --git a/examples/test_index_udf.prg b/examples/test_index_udf.prg
new file mode 100644
index 0000000..5ec5007
--- /dev/null
+++ b/examples/test_index_udf.prg
@@ -0,0 +1,55 @@
+// Test INDEX ON with User Defined Functions
+PROCEDURE Main()
+   LOCAL i, aStruct, aCit, nCidx
+
+   aStruct := {{"ID","N",6,0}, {"NAME","C",20,0}, {"CITY","C",15,0}}
+   dbCreate("udf_test", aStruct)
+   USE "udf_test" NEW
+
+   aCit := {"Seoul","Tokyo","Beijing"}
+   FOR i := 1 TO 10
+      APPEND BLANK
+      REPLACE ID   WITH i
+      REPLACE NAME WITH PadR("Name_" + PadL(LTrim(Str(i)), 3, "0"), 20)
+      nCidx := Int((i-1) % 3) + 1
+      REPLACE CITY WITH PadR(aCit[nCidx], 15)
+   NEXT
+   ? "Records:", RecCount()
+
+   // Test 1: INDEX ON with built-in function (baseline)
+   INDEX ON UPPER(NAME) TO udf_idx1
+   GO TOP
+   ? "T1 UPPER top:", RTrim(FieldGet(2)), RecNo()
+   SEEK PadR("NAME_005", 20)
+   ? "T2 UPPER seek:", Found(), RecNo()
+
+   // Test 2: INDEX ON with UDF
+   INDEX ON MyKey(FIELD->NAME) TO udf_idx2
+   GO TOP
+   ? "T3 UDF top:", RTrim(FieldGet(2)), RecNo()
+   SEEK PadR("KEY:Name_001", 20)
+   ? "T4 UDF seek:", Found(), RecNo()
+
+   // Test 3: INDEX ON with two-param UDF
+   INDEX ON CityKey(FIELD->CITY, FIELD->NAME) TO udf_idx3
+   GO TOP
+   ? "T5 UDF2 top:", RTrim(FieldGet(3)), RTrim(FieldGet(2)), RecNo()
+
+   // Test 4: Nested: built-in wrapping UDF
+   INDEX ON Left(MyKey(FIELD->NAME), 15) TO udf_idx4
+   GO TOP
+   ? "T6 Nested top:", RTrim(FieldGet(2)), RecNo()
+
+   CLOSE ALL
+   ? "DONE"
+RETURN
+
+FUNCTION MyKey(cName)
+   LOCAL cResult
+   cResult := "KEY:" + RTrim(cName)
+RETURN PadR(cResult, 20)
+
+FUNCTION CityKey(cCity, cName)
+   LOCAL cResult
+   cResult := RTrim(cCity) + ":" + RTrim(cName)
+RETURN PadR(cResult, 30)
diff --git a/hbrdd/dbf/indexer.go b/hbrdd/dbf/indexer.go
index b4df5d2..fa272a8 100644
--- a/hbrdd/dbf/indexer.go
+++ b/hbrdd/dbf/indexer.go
@@ -46,6 +46,12 @@ type indexState struct {
 	scopeBottom []byte       // bottom scope key (nil = no scope)
 }
 
+// KeyEvalFunc is a callback for evaluating index key expressions via the VM.
+// Set by the generated code (via SetKeyEval) before calling OrderCreate.
+// This allows evalKeyExprInner to call UDFs and evaluate complex expressions.
+// Signature: func(exprString) → Value (called on the current Thread)
+var KeyEvalFunc func(expr string) hbrt.Value
+
 // ensureIndexState initializes the index state if nil.
 func (a *DBFArea) ensureIndexState() {
 	if a.idxState == nil {
@@ -848,9 +854,16 @@ func (a *DBFArea) evalKeyExprInner(expr string) []byte {
 				}
 				return []byte(inner[:width])
 			}
+		default:
+			// Unknown function — use VM MacroEval for UDF calls
+			if KeyEvalFunc != nil {
+				fullExpr := expr[:parenOpen] + "(" + argsStr + ")"
+				val := KeyEvalFunc(fullExpr)
+				return valueToKeyBytes(val)
+			}
+			// Fallback: evaluate inner as field
+			return a.evalKeyExprInner(argsStr)
 		}
-		// Unknown function — try to evaluate inner as field
-		return a.evalKeyExprInner(argsStr)
 	}
 
 	// Concatenation: expr1 + expr2 (find + not inside parens)
@@ -866,6 +879,12 @@ func (a *DBFArea) evalKeyExprInner(expr string) []byte {
 		return []byte(s)
 	}
 
+	// Final fallback: use VM MacroEval for any unresolvable expression
+	if KeyEvalFunc != nil {
+		val := KeyEvalFunc(expr)
+		return valueToKeyBytes(val)
+	}
+
 	return []byte(expr)
 }
 
@@ -937,6 +956,26 @@ func (a *DBFArea) evalForInner(expr string) bool {
 	return true // default: include record
 }
 
+// valueToKeyBytes converts a hbrt.Value to index key bytes.
+func valueToKeyBytes(v hbrt.Value) []byte {
+	switch {
+	case v.IsString():
+		return []byte(v.AsString())
+	case v.IsNumeric():
+		return []byte(fmt.Sprintf("%20.10f", v.AsNumDouble()))
+	case v.IsDate(), v.IsTimestamp():
+		y, m, d := julianToDate(v.AsJulian())
+		return []byte(fmt.Sprintf("%04d%02d%02d", y, m, d))
+	case v.IsLogical():
+		if v.AsBool() {
+			return []byte("T")
+		}
+		return []byte("F")
+	default:
+		return []byte("")
+	}
+}
+
 // Helper: find matching close parenthesis
 func findMatchingParen(s string, openPos int) int {
 	depth := 1