diff --git a/src/prism.c b/src/prism.c
index 280dc5144c..bc516cbf4c 100644
--- a/src/prism.c
+++ b/src/prism.c
@@ -21407,6 +21407,33 @@ parse_expression_infix(pm_parser_t *parser, pm_node_t *node, pm_binding_power_t
         case PM_TOKEN_STAR:
         case PM_TOKEN_STAR_STAR: {
             parser_lex(parser);
+            pm_token_t operator = parser->previous;
+            switch (PM_NODE_TYPE(node)) {
+                case PM_RESCUE_MODIFIER_NODE: {
+                    pm_rescue_modifier_node_t *cast = (pm_rescue_modifier_node_t *) node;
+                    if (PM_NODE_TYPE_P(cast->rescue_expression, PM_MATCH_PREDICATE_NODE) || PM_NODE_TYPE_P(cast->rescue_expression, PM_MATCH_REQUIRED_NODE)) {
+                        PM_PARSER_ERR_TOKEN_FORMAT(parser, operator, PM_ERR_EXPECT_EOL_AFTER_STATEMENT, pm_token_type_human(operator.type));
+                    }
+                    break;
+                }
+                case PM_AND_NODE: {
+                    pm_and_node_t *cast = (pm_and_node_t *) node;
+                    if (PM_NODE_TYPE_P(cast->right, PM_MATCH_PREDICATE_NODE) || PM_NODE_TYPE_P(cast->right, PM_MATCH_REQUIRED_NODE)) {
+                        PM_PARSER_ERR_TOKEN_FORMAT(parser, operator, PM_ERR_EXPECT_EOL_AFTER_STATEMENT, pm_token_type_human(operator.type));
+                    }
+                    break;
+                }
+                case PM_OR_NODE: {
+                    pm_or_node_t *cast = (pm_or_node_t *) node;
+                    if (PM_NODE_TYPE_P(cast->right, PM_MATCH_PREDICATE_NODE) || PM_NODE_TYPE_P(cast->right, PM_MATCH_REQUIRED_NODE)) {
+                        PM_PARSER_ERR_TOKEN_FORMAT(parser, operator, PM_ERR_EXPECT_EOL_AFTER_STATEMENT, pm_token_type_human(operator.type));
+                    }
+                    break;
+                }
+                default:
+                    break;
+            }
+
             pm_node_t *argument = parse_expression(parser, binding_power, false, false, PM_ERR_EXPECT_EXPRESSION_AFTER_OPERATOR, (uint16_t) (depth + 1));
             return (pm_node_t *) pm_call_node_binary_create(parser, node, &token, argument, 0);
         }
diff --git a/test/prism/errors/match_predicate_after_and_with_opreator.txt b/test/prism/errors/match_predicate_after_and_with_opreator.txt
new file mode 100644
index 0000000000..5a0c5925ea
--- /dev/null
+++ b/test/prism/errors/match_predicate_after_and_with_opreator.txt
@@ -0,0 +1,3 @@
+1 and 2 in 3 % 4
+             ^ unexpected '%', expecting end-of-input
+
diff --git a/test/prism/errors/match_predicate_after_or_with_opreator.txt b/test/prism/errors/match_predicate_after_or_with_opreator.txt
new file mode 100644
index 0000000000..8ea69e4787
--- /dev/null
+++ b/test/prism/errors/match_predicate_after_or_with_opreator.txt
@@ -0,0 +1,3 @@
+1 or 2 in 3 + 4
+            ^ unexpected '+', expecting end-of-input
+
diff --git a/test/prism/errors/match_predicate_after_rescue_with_opreator.txt b/test/prism/errors/match_predicate_after_rescue_with_opreator.txt
new file mode 100644
index 0000000000..b2363a544d
--- /dev/null
+++ b/test/prism/errors/match_predicate_after_rescue_with_opreator.txt
@@ -0,0 +1,3 @@
+1 rescue 2 in 3 << 4
+                ^~ unexpected <<, expecting end-of-input
+
diff --git a/test/prism/errors/match_required_after_and_with_opreator.txt b/test/prism/errors/match_required_after_and_with_opreator.txt
new file mode 100644
index 0000000000..eafbc1f12a
--- /dev/null
+++ b/test/prism/errors/match_required_after_and_with_opreator.txt
@@ -0,0 +1,3 @@
+1 and 2 => 3 - 4
+             ^ unexpected '-', expecting end-of-input
+
diff --git a/test/prism/errors/match_required_after_or_with_opreator.txt b/test/prism/errors/match_required_after_or_with_opreator.txt
new file mode 100644
index 0000000000..c35f3b66e4
--- /dev/null
+++ b/test/prism/errors/match_required_after_or_with_opreator.txt
@@ -0,0 +1,3 @@
+1 or 2 => 3 ^ 4
+            ^ unexpected '^', expecting end-of-input
+
diff --git a/test/prism/errors/match_required_after_rescue_with_opreator.txt b/test/prism/errors/match_required_after_rescue_with_opreator.txt
new file mode 100644
index 0000000000..903e2ccc8e
--- /dev/null
+++ b/test/prism/errors/match_required_after_rescue_with_opreator.txt
@@ -0,0 +1,3 @@
+1 rescue 2 => 3 ** 4
+                ^~ unexpected '**', expecting end-of-input
+