diff --git a/prism_compile.c b/prism_compile.c
index 26d94e979d..dd5f920fb4 100644
--- a/prism_compile.c
+++ b/prism_compile.c
@@ -8785,7 +8785,7 @@ pm_parse_file_script_lines(const pm_scope_node_t *scope_node, const pm_parser_t
  * be read.
  */
 VALUE
-pm_load_file(pm_parse_result_t *result, VALUE filepath)
+pm_load_file(pm_parse_result_t *result, VALUE filepath, bool load_error)
 {
     if (!pm_string_mapped_init(&result->input, RSTRING_PTR(filepath))) {
 #ifdef _WIN32
@@ -8794,9 +8794,21 @@ pm_load_file(pm_parse_result_t *result, VALUE filepath)
         int e = errno;
 #endif
 
-        VALUE err = rb_syserr_new(e, RSTRING_PTR(filepath));
-        RB_GC_GUARD(filepath);
-        return err;
+        VALUE error;
+
+        if (load_error) {
+            VALUE message = rb_str_buf_new_cstr(strerror(e));
+            rb_str_cat2(message, " -- ");
+            rb_str_append(message, filepath);
+
+            error = rb_exc_new3(rb_eLoadError, message);
+            rb_ivar_set(error, rb_intern_const("@path"), filepath);
+        } else {
+            error = rb_syserr_new(e, RSTRING_PTR(filepath));
+            RB_GC_GUARD(filepath);
+        }
+
+        return error;
     }
 
     pm_options_frozen_string_literal_init(&result->options);
@@ -8843,7 +8855,7 @@ pm_parse_file(pm_parse_result_t *result, VALUE filepath)
 VALUE
 pm_load_parse_file(pm_parse_result_t *result, VALUE filepath)
 {
-    VALUE error = pm_load_file(result, filepath);
+    VALUE error = pm_load_file(result, filepath, false);
     if (NIL_P(error)) {
         error = pm_parse_file(result, filepath);
     }
diff --git a/prism_compile.h b/prism_compile.h
index e58bed271f..0f82782ec0 100644
--- a/prism_compile.h
+++ b/prism_compile.h
@@ -72,7 +72,7 @@ typedef struct {
     bool parsed;
 } pm_parse_result_t;
 
-VALUE pm_load_file(pm_parse_result_t *result, VALUE filepath);
+VALUE pm_load_file(pm_parse_result_t *result, VALUE filepath, bool load_error);
 VALUE pm_parse_file(pm_parse_result_t *result, VALUE filepath);
 VALUE pm_load_parse_file(pm_parse_result_t *result, VALUE filepath);
 VALUE pm_parse_string(pm_parse_result_t *result, VALUE source, VALUE filepath);
diff --git a/ruby.c b/ruby.c
index e939320f1f..d86549066d 100644
--- a/ruby.c
+++ b/ruby.c
@@ -2157,7 +2157,7 @@ prism_script(ruby_cmdline_options_t *opt, pm_parse_result_t *result)
     }
     else {
         pm_options_command_line_set(options, command_line);
-        error = pm_load_file(result, opt->script_name);
+        error = pm_load_file(result, opt->script_name, true);
 
         // If reading the file did not error, at that point we load the command
         // line options. We do it in this order so that if the main script fails
diff --git a/spec/prism.mspec b/spec/prism.mspec
index 190ee6fb36..ff84fb053d 100644
--- a/spec/prism.mspec
+++ b/spec/prism.mspec
@@ -19,8 +19,6 @@ MSpec.register(:exclude, "Regexps with encoding modifiers preserves UTF-8 as /u
 MSpec.register(:exclude, "A Symbol literal raises an SyntaxError at parse time when Symbol with invalid bytes")
 
 ## Core
-MSpec.register(:exclude, "IO.popen with a leading Array argument accepts a trailing Hash of Process.exec options")
-MSpec.register(:exclude, "IO.popen with a leading Array argument accepts an IO mode argument following the Array")
 MSpec.register(:exclude, "TracePoint#inspect returns a String showing the event, method, path and line for a :return event")
 MSpec.register(:exclude, "TracePoint.new includes multiple events when multiple event names are passed as params")
 MSpec.register(:exclude, "TracePoint#path equals \"(eval at __FILE__:__LINE__)\" inside an eval for :end event")