diff --git a/vlib/v/parser/expr.v b/vlib/v/parser/expr.v
index 08503b01c7..d82130d227 100644
--- a/vlib/v/parser/expr.v
+++ b/vlib/v/parser/expr.v
@@ -666,7 +666,17 @@ fn (mut p Parser) infix_expr(left ast.Expr) ast.Expr {
 		p.inside_in_array = true
 	}
 
+	right_op_pos := p.tok.pos()
 	right = p.expr(precedence)
+	if op in [.plus, .minus, .mul, .div, .mod, .lt, .eq] && mut right is ast.PrefixExpr {
+		mut right_expr := right.right
+		for mut right_expr is ast.ParExpr {
+			right_expr = right_expr.expr
+		}
+		if right.op in [.plus, .minus, .mul, .div, .mod, .lt, .eq] && right_expr.is_pure_literal() {
+			p.error_with_pos('invalid expression: unexpected token `${op}`', right_op_pos)
+		}
+	}
 	if is_key_in {
 		p.inside_in_array = false
 	}
diff --git a/vlib/v/parser/tests/prefix_err_1.out b/vlib/v/parser/tests/prefix_err_1.out
new file mode 100644
index 0000000000..974bf684f1
--- /dev/null
+++ b/vlib/v/parser/tests/prefix_err_1.out
@@ -0,0 +1,3 @@
+vlib/v/parser/tests/prefix_err_1.vv:1:9: error: invalid expression: unexpected token `-`
+    1 | _ = 5 - - -5
+      |         ^
diff --git a/vlib/v/parser/tests/prefix_err_1.vv b/vlib/v/parser/tests/prefix_err_1.vv
new file mode 100644
index 0000000000..04f48354be
--- /dev/null
+++ b/vlib/v/parser/tests/prefix_err_1.vv
@@ -0,0 +1 @@
+_ = 5 - - -5
diff --git a/vlib/v/parser/tests/prefix_err_2.out b/vlib/v/parser/tests/prefix_err_2.out
new file mode 100644
index 0000000000..65d09ba0d7
--- /dev/null
+++ b/vlib/v/parser/tests/prefix_err_2.out
@@ -0,0 +1,3 @@
+vlib/v/parser/tests/prefix_err_2.vv:1:9: error: invalid expression: unexpected token `-`
+    1 | _ = 5 - - (((-5)))
+      |         ^
diff --git a/vlib/v/parser/tests/prefix_err_2.vv b/vlib/v/parser/tests/prefix_err_2.vv
new file mode 100644
index 0000000000..74edf5d7e0
--- /dev/null
+++ b/vlib/v/parser/tests/prefix_err_2.vv
@@ -0,0 +1 @@
+_ = 5 - - (((-5)))