diff --git a/common.mk b/common.mk
index 171c7dfd30cc6c..5a929fc937fbef 100644
--- a/common.mk
+++ b/common.mk
@@ -8495,6 +8495,7 @@ iseq.$(OBJEXT): $(top_srcdir)/internal/fixnum.h
 iseq.$(OBJEXT): $(top_srcdir)/internal/gc.h
 iseq.$(OBJEXT): $(top_srcdir)/internal/hash.h
 iseq.$(OBJEXT): $(top_srcdir)/internal/imemo.h
+iseq.$(OBJEXT): $(top_srcdir)/internal/io.h
 iseq.$(OBJEXT): $(top_srcdir)/internal/numeric.h
 iseq.$(OBJEXT): $(top_srcdir)/internal/parse.h
 iseq.$(OBJEXT): $(top_srcdir)/internal/rational.h
@@ -8702,6 +8703,7 @@ iseq.$(OBJEXT): {$(VPATH)}internal/value_type.h
 iseq.$(OBJEXT): {$(VPATH)}internal/variable.h
 iseq.$(OBJEXT): {$(VPATH)}internal/warning_push.h
 iseq.$(OBJEXT): {$(VPATH)}internal/xmalloc.h
+iseq.$(OBJEXT): {$(VPATH)}io.h
 iseq.$(OBJEXT): {$(VPATH)}iseq.c
 iseq.$(OBJEXT): {$(VPATH)}iseq.h
 iseq.$(OBJEXT): {$(VPATH)}method.h
diff --git a/iseq.c b/iseq.c
index 27c5bb5d82d907..f2911b43f26962 100644
--- a/iseq.c
+++ b/iseq.c
@@ -28,6 +28,7 @@
 #include "internal/file.h"
 #include "internal/gc.h"
 #include "internal/hash.h"
+#include "internal/io.h"
 #include "internal/ruby_parser.h"
 #include "internal/sanitizers.h"
 #include "internal/symbol.h"
@@ -1404,19 +1405,36 @@ static void
 iseqw_s_compile_prism_compile(pm_parser_t *parser, VALUE opt, rb_iseq_t *iseq, VALUE file, VALUE path, int first_lineno)
 {
     pm_node_t *node = pm_parse(parser);
-    rb_code_location_t code_location;
-    pm_code_location(&code_location, &parser->newline_list, &node->location);
 
-    rb_compile_option_t option;
-    make_compile_option(&option, opt);
-    prepare_iseq_build(iseq, rb_fstring_lit("<compiled>"), file, path, first_lineno, &code_location, -1, NULL, 0, ISEQ_TYPE_TOP, Qnil, &option);
+    if (parser->error_list.size > 0) {
+        pm_buffer_t buffer = { 0 };
+        pm_parser_errors_format(parser, &buffer, rb_stderr_tty_p());
 
-    pm_scope_node_t scope_node;
-    pm_scope_node_init(node, &scope_node, NULL, parser);
-    rb_iseq_compile_prism_node(iseq, &scope_node, parser);
+        pm_buffer_prepend_string(&buffer, "syntax errors found\n", 20);
+        VALUE error = rb_exc_new(rb_eSyntaxError, pm_buffer_value(&buffer), pm_buffer_length(&buffer));
 
-    finish_iseq_build(iseq);
-    pm_node_destroy(parser, node);
+        pm_buffer_free(&buffer);
+        pm_node_destroy(parser, node);
+
+        // TODO: We need to set the backtrace based on the ISEQ.
+        // VALUE path = pathobj_path(ISEQ_BODY(iseq)->location.pathobj);
+        // rb_funcallv(error, rb_intern("set_backtrace"), 1, &path);
+        rb_exc_raise(error);
+    } else {
+        rb_code_location_t code_location;
+        pm_code_location(&code_location, &parser->newline_list, &node->location);
+
+        rb_compile_option_t option;
+        make_compile_option(&option, opt);
+        prepare_iseq_build(iseq, rb_fstring_lit("<compiled>"), file, path, first_lineno, &code_location, -1, NULL, 0, ISEQ_TYPE_TOP, Qnil, &option);
+
+        pm_scope_node_t scope_node;
+        pm_scope_node_init(node, &scope_node, NULL, parser);
+        rb_iseq_compile_prism_node(iseq, &scope_node, parser);
+
+        finish_iseq_build(iseq);
+        pm_node_destroy(parser, node);
+    }
 }
 
 static VALUE
diff --git a/test/ruby/test_iseq.rb b/test/ruby/test_iseq.rb
index b0896511d8337f..f5c0b8205718dc 100644
--- a/test/ruby/test_iseq.rb
+++ b/test/ruby/test_iseq.rb
@@ -801,12 +801,15 @@ def test_ibf_bignum
 
   def test_compile_prism_with_file
     Tempfile.create(%w"test_iseq .rb") do |f|
-      f.puts "name = 'Prism'; puts 'hello"
+      f.puts "name = 'Prism'; puts 'hello'"
       f.close
 
-      assert_nothing_raised(SyntaxError) {
-        RubyVM::InstructionSequence.compile_prism(f.path)
-      }
+      assert_nothing_raised(TypeError) do
+        begin
+          RubyVM::InstructionSequence.compile_prism(f.path)
+        rescue SyntaxError
+        end
+      end
     end
   end
 end