diff --git a/internal/literals/literals.go b/internal/literals/literals.go
index c5ebae1..07dee56 100644
--- a/internal/literals/literals.go
+++ b/internal/literals/literals.go
@@ -113,7 +113,7 @@ func Obfuscate(file *ast.File, info *types.Info, fset *token.FileSet, ignoreObj
 
 					data[i] = byte(value)
 				}
-				cursor.Replace(obfuscateByteArray(data, y.Len()))
+				cursor.Replace(withPos(obfuscateByteArray(data, y.Len()), x.Pos()))
 
 			case *types.Slice:
 				if y.Elem() != byteType {
@@ -138,7 +138,7 @@ func Obfuscate(file *ast.File, info *types.Info, fset *token.FileSet, ignoreObj
 
 					data = append(data, byte(value))
 				}
-				cursor.Replace(obfuscateByteSlice(data))
+				cursor.Replace(withPos(obfuscateByteSlice(data), x.Pos()))
 
 			}
 
@@ -168,7 +168,7 @@ func Obfuscate(file *ast.File, info *types.Info, fset *token.FileSet, ignoreObj
 				return true
 			}
 
-			cursor.Replace(obfuscateString(value))
+			cursor.Replace(withPos(obfuscateString(value), x.Pos()))
 		}
 
 		return true
@@ -177,6 +177,44 @@ func Obfuscate(file *ast.File, info *types.Info, fset *token.FileSet, ignoreObj
 	return astutil.Apply(file, pre, post).(*ast.File)
 }
 
+// withPos sets any token.Pos fields under node which affect printing to pos.
+// Note that we can't set all token.Pos fields, since some affect the semantics.
+//
+// This function is useful so that go/printer doesn't try to estimate position
+// offsets, which can end up in printing comment directives too early.
+//
+// We don't set any "end" or middle positions, because they seem irrelevant.
+func withPos(node ast.Node, pos token.Pos) ast.Node {
+	ast.Inspect(node, func(node ast.Node) bool {
+		switch node := node.(type) {
+		case *ast.BasicLit:
+			node.ValuePos = pos
+		case *ast.Ident:
+			node.NamePos = pos
+		case *ast.StarExpr:
+			node.Star = pos
+		case *ast.CompositeLit:
+			node.Lbrace = pos
+		case *ast.ArrayType:
+			node.Lbrack = pos
+		case *ast.FuncType:
+			node.Func = pos
+		case *ast.GenDecl:
+			node.TokPos = pos
+		case *ast.ReturnStmt:
+			node.Return = pos
+		case *ast.ForStmt:
+			node.For = pos
+		case *ast.RangeStmt:
+			node.For = pos
+		case *ast.CallExpr:
+			node.Lparen = pos
+		}
+		return true
+	})
+	return node
+}
+
 func obfuscateString(data string) *ast.CallExpr {
 	obfuscator := randObfuscator()
 	block := obfuscator.obfuscate([]byte(data))
diff --git a/position.go b/position.go
index e255236..a045b22 100644
--- a/position.go
+++ b/position.go
@@ -51,7 +51,7 @@ func printFile(file1 *ast.File) ([]byte, error) {
 	// The only way we can get the final ones is to parse again.
 	file2, err := parser.ParseFile(fset, absFilename, src, parser.ParseComments)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("re-parse error: %w", err)
 	}
 
 	// Keep the compiler directives, and change position info.
diff --git a/testdata/scripts/literals.txt b/testdata/scripts/literals.txt
index 25d8b1a..d097b24 100644
--- a/testdata/scripts/literals.txt
+++ b/testdata/scripts/literals.txt
@@ -242,6 +242,55 @@ const (
 	iota0 uint8 = iota
 	iota1
 )
+-- directives.go --
+// If we misplace any of the directives below,
+// cmd/compile will complain with "misplaced compiler directive".
+//
+// We use many literals and functions, mixing different types,
+// so that it's more likely that bugs will be caught.
+package main
+
+//go:noinline
+func str0() { println("foo") }
+
+//go:noinline
+func str1() { println("foo") }
+
+//go:noinline
+func str2() { println("foo") }
+
+//go:noinline
+func str3() { println("foo") }
+
+//go:noinline
+func str4() { println("foo") }
+
+//go:noinline
+func arr0() { println(len([...]byte{0, 1, 2})) }
+
+//go:noinline
+func arr1() { println(len([...]byte{0, 1, 2})) }
+
+//go:noinline
+func slc0() { println([]byte{0, 1, 2}) }
+
+//go:noinline
+func slc1() { println([]byte{0, 1, 2}) }
+
+//go:noinline
+func str5() { println("foo") }
+
+//go:noinline
+func str6() { println("foo") }
+
+//go:noinline
+func str7() { println("foo") }
+
+//go:noinline
+func str8() { println("foo") }
+
+//go:noinline
+func str9() { println("foo") }
 
 -- main.stderr --
 Lorem true