diff --git a/config.yml b/config.yml
index 876008311f..cc07b386a1 100644
--- a/config.yml
+++ b/config.yml
@@ -187,6 +187,7 @@ errors:
   - MULTI_ASSIGN_UNEXPECTED_REST
   - NESTING_TOO_DEEP
   - NO_LOCAL_VARIABLE
+  - NON_ASSOCIATIVE_OPERATOR
   - NOT_EXPRESSION
   - NUMBER_LITERAL_UNDERSCORE
   - NUMBERED_PARAMETER_INNER_BLOCK
diff --git a/gemfiles/jruby/Gemfile.lock b/gemfiles/jruby/Gemfile.lock
index 404e48332d..c38dc3cea5 100644
--- a/gemfiles/jruby/Gemfile.lock
+++ b/gemfiles/jruby/Gemfile.lock
@@ -20,8 +20,10 @@ GEM
 
 PLATFORMS
   universal-java-11
+  universal-java-17
   universal-java-20
   universal-java-21
+  universal-java-22
 
 DEPENDENCIES
   parser
diff --git a/src/prism.c b/src/prism.c
index 6e3f9bce59..808915858a 100644
--- a/src/prism.c
+++ b/src/prism.c
@@ -21643,16 +21643,26 @@ parse_expression(pm_parser_t *parser, pm_binding_power_t binding_power, bool acc
                 break;
         }
 
+        // If the operator is nonassoc and we should not be able to parse the
+        // upcoming infix operator, break.
         if (current_binding_powers.nonassoc) {
-            bool endless_range_p = PM_NODE_TYPE_P(node, PM_RANGE_NODE) && ((pm_range_node_t *) node)->right == NULL;
-            pm_binding_power_t left = endless_range_p ? PM_BINDING_POWER_TERM : current_binding_powers.left;
-            if (
-                left <= pm_binding_powers[parser->current.type].left ||
-                // Exceptionally to operator precedences, '1.. & 2' is rejected.
-                // '1.. || 2' is also an exception, but it is handled by the lexer.
-                // (Here, parser->current is PM_TOKEN_PIPE, not PM_TOKEN_PIPE_PIPE).
-                (endless_range_p && match1(parser, PM_TOKEN_AMPERSAND))
-            ) {
+            // If this is an endless range, then we need to reject a couple of
+            // additional operators because it violates the normal operator
+            // precedence rules. Those patterns are:
+            //
+            //     1.. & 2
+            //     1.. * 2
+            //
+            if (PM_NODE_TYPE_P(node, PM_RANGE_NODE) && ((pm_range_node_t *) node)->right == NULL) {
+                if (match3(parser, PM_TOKEN_UAMPERSAND, PM_TOKEN_USTAR, PM_TOKEN_DOT)) {
+                    PM_PARSER_ERR_TOKEN_FORMAT(parser, parser->current, PM_ERR_NON_ASSOCIATIVE_OPERATOR, pm_token_type_human(parser->current.type), pm_token_type_human(parser->previous.type));
+                    break;
+                }
+
+                if (PM_BINDING_POWER_TERM <= pm_binding_powers[parser->current.type].left) {
+                    break;
+                }
+            } else if (current_binding_powers.left <= pm_binding_powers[parser->current.type].left) {
                 break;
             }
         }
diff --git a/templates/src/diagnostic.c.erb b/templates/src/diagnostic.c.erb
index d3b9cd516d..7768c7f5ed 100644
--- a/templates/src/diagnostic.c.erb
+++ b/templates/src/diagnostic.c.erb
@@ -269,6 +269,7 @@ static const pm_diagnostic_data_t diagnostic_messages[PM_DIAGNOSTIC_ID_MAX] = {
     [PM_ERR_MULTI_ASSIGN_UNEXPECTED_REST]       = { "unexpected '%.*s' resulting in multiple splats in multiple assignment", PM_ERROR_LEVEL_SYNTAX },
     [PM_ERR_NESTING_TOO_DEEP]                   = { "nesting too deep", PM_ERROR_LEVEL_SYNTAX },
     [PM_ERR_NO_LOCAL_VARIABLE]                  = { "%.*s: no such local variable", PM_ERROR_LEVEL_SYNTAX },
+    [PM_ERR_NON_ASSOCIATIVE_OPERATOR]           = { "unexpected %s; %s is a non-associative operator", PM_ERROR_LEVEL_SYNTAX },
     [PM_ERR_NOT_EXPRESSION]                     = { "expected an expression after `not`", PM_ERROR_LEVEL_SYNTAX },
     [PM_ERR_NUMBER_LITERAL_UNDERSCORE]          = { "number literal ending with a `_`", PM_ERROR_LEVEL_SYNTAX },
     [PM_ERR_NUMBERED_PARAMETER_INNER_BLOCK]     = { "numbered parameter is already used in inner block", PM_ERROR_LEVEL_SYNTAX },
diff --git a/test/prism/errors/non_assoc_range.txt b/test/prism/errors/non_assoc_range.txt
index 072cf6d3c6..12eec10594 100644
--- a/test/prism/errors/non_assoc_range.txt
+++ b/test/prism/errors/non_assoc_range.txt
@@ -1,4 +1,5 @@
 1....2
+    ^ unexpected '.'; ... is a non-associative operator
     ^ unexpected '.', expecting end-of-input
     ^ unexpected '.', ignoring it
 
diff --git a/test/prism/errors/range_and_bin_op_4.txt b/test/prism/errors/range_and_bin_op_4.txt
index 56226480cf..ce6e79e5ff 100644
--- a/test/prism/errors/range_and_bin_op_4.txt
+++ b/test/prism/errors/range_and_bin_op_4.txt
@@ -1,4 +1,5 @@
 1.. & 2
+    ^ unexpected '&'; .. is a non-associative operator
     ^ unexpected '&', expecting end-of-input
     ^ unexpected '&', ignoring it
 
diff --git a/test/prism/errors/range_and_bin_op_5.txt b/test/prism/errors/range_and_bin_op_5.txt
index bc8b467914..4ed91e1052 100644
--- a/test/prism/errors/range_and_bin_op_5.txt
+++ b/test/prism/errors/range_and_bin_op_5.txt
@@ -1,4 +1,5 @@
 1.. * 2
+    ^ unexpected *; .. is a non-associative operator
     ^ unexpected *, expecting end-of-input
       ^ unexpected write target
     ^~~ unexpected write target