diff --git a/lib/prism/lex_compat.rb b/lib/prism/lex_compat.rb
index e8d2ce1b19..3d5cbfcddc 100644
--- a/lib/prism/lex_compat.rb
+++ b/lib/prism/lex_compat.rb
@@ -768,21 +768,24 @@ def result
         source.byte_offset(line, column)
       end
 
-      # Add :on_sp tokens
-      tokens = insert_on_sp(tokens, source, result.data_loc, bom, eof_token)
+      tokens = post_process_tokens(tokens, source, result.data_loc, bom, eof_token)
 
       Result.new(tokens, result.comments, result.magic_comments, result.data_loc, result.errors, result.warnings, source)
     end
 
     private
 
-    def insert_on_sp(tokens, source, data_loc, bom, eof_token)
+    def post_process_tokens(tokens, source, data_loc, bom, eof_token)
       new_tokens = []
 
       prev_token_state = Translation::Ripper::Lexer::State[Translation::Ripper::EXPR_BEG]
       prev_token_end = bom ? 3 : 0
 
       tokens.each do |token|
+        # Skip missing heredoc ends.
+        next if token[1] == :on_heredoc_end && token[2] == ""
+
+        # Add :on_sp tokens.
         line, column = token[0]
         start_offset = source.byte_offset(line, column)
 
diff --git a/src/prism.c b/src/prism.c
index 34e5d38b0a..097b4c7305 100644
--- a/src/prism.c
+++ b/src/prism.c
@@ -9856,6 +9856,15 @@ parser_lex(pm_parser_t *parser) {
             // We'll check if we're at the end of the file. If we are, then we
             // need to return the EOF token.
             if (parser->current.end >= parser->end) {
+                // We may be missing closing tokens. We should pop modes one by one
+                // to do the appropriate cleanup like moving next_start for heredocs.
+                // Only when no mode is remaining will we actually emit the EOF token.
+                if (parser->lex_modes.current->mode != PM_LEX_DEFAULT) {
+                    lex_mode_pop(parser);
+                    parser_lex(parser);
+                    return;
+                }
+
                 // If we hit EOF, but the EOF came immediately after a newline,
                 // set the start of the token to the newline.  This way any EOF
                 // errors will be reported as happening on that line rather than
diff --git a/test/prism/errors/unterminated_heredoc_and_embexpr.txt b/test/prism/errors/unterminated_heredoc_and_embexpr.txt
new file mode 100644
index 0000000000..bed7fcd24e
--- /dev/null
+++ b/test/prism/errors/unterminated_heredoc_and_embexpr.txt
@@ -0,0 +1,11 @@
+<<A+B
+  ^ unterminated heredoc; can't find string "A" anywhere before EOF
+   ^ unexpected '+', ignoring it
+  ^ unterminated heredoc; can't find string "A" anywhere before EOF
+#{C
+   ^ unexpected heredoc ending; expected an argument
+   ^ unexpected heredoc ending, expecting end-of-input
+   ^ unexpected heredoc ending, ignoring it
+   ^ unexpected end-of-input, assuming it is closing the parent top level context
+^ expected a `}` to close the embedded expression
+
diff --git a/test/prism/errors/unterminated_heredoc_and_embexpr_2.txt b/test/prism/errors/unterminated_heredoc_and_embexpr_2.txt
new file mode 100644
index 0000000000..a03ff1d212
--- /dev/null
+++ b/test/prism/errors/unterminated_heredoc_and_embexpr_2.txt
@@ -0,0 +1,9 @@
+<<A+B
+  ^ unterminated heredoc; can't find string "A" anywhere before EOF
+#{C + "#{"}
+           ^ unterminated string meets end of file
+           ^ unexpected end-of-input, assuming it is closing the parent top level context
+           ^ expected a `}` to close the embedded expression
+      ^ unterminated string; expected a closing delimiter for the interpolated string
+           ^ expected a `}` to close the embedded expression
+
diff --git a/test/prism/lex_test.rb b/test/prism/lex_test.rb
index 9a9f203c28..8ea7ce7e9b 100644
--- a/test/prism/lex_test.rb
+++ b/test/prism/lex_test.rb
@@ -48,11 +48,58 @@ def test_parse_lex_file
     end
 
     if RUBY_VERSION >= "3.3"
-      def test_lex_compare
-        prism = Prism.lex_compat(File.read(__FILE__), version: "current").value
-        ripper = Ripper.lex(File.read(__FILE__))
+      def test_lex_compat
+        source = "foo bar"
+        prism = Prism.lex_compat(source, version: "current").value
+        ripper = Ripper.lex(source)
         assert_equal(ripper, prism)
       end
     end
+
+    def test_lex_interpolation_unterminated
+      assert_equal(
+        %i[STRING_BEGIN EMBEXPR_BEGIN EOF],
+        token_types('"#{')
+      )
+
+      assert_equal(
+        %i[STRING_BEGIN EMBEXPR_BEGIN IGNORED_NEWLINE EOF],
+        token_types('"#{' + "\n")
+      )
+    end
+
+    def test_lex_interpolation_unterminated_with_content
+      # FIXME: Emits EOL twice.
+      assert_equal(
+        %i[STRING_BEGIN EMBEXPR_BEGIN CONSTANT EOF EOF],
+        token_types('"#{C')
+      )
+
+      assert_equal(
+        %i[STRING_BEGIN EMBEXPR_BEGIN CONSTANT NEWLINE EOF],
+        token_types('"#{C' + "\n")
+      )
+    end
+
+    def test_lex_heredoc_unterminated
+      code = <<~'RUBY'.strip
+        <<A+B
+        #{C
+      RUBY
+
+      assert_equal(
+        %i[HEREDOC_START EMBEXPR_BEGIN CONSTANT HEREDOC_END PLUS CONSTANT NEWLINE EOF],
+        token_types(code)
+      )
+
+      assert_equal(
+        %i[HEREDOC_START EMBEXPR_BEGIN CONSTANT NEWLINE HEREDOC_END PLUS CONSTANT NEWLINE EOF],
+        token_types(code + "\n")
+      )
+    end
+
+    def token_types(code)
+      Prism.lex(code).value.map { |token, _state| token.type }
+    end
   end
 end
diff --git a/test/prism/ruby/ripper_test.rb b/test/prism/ruby/ripper_test.rb
index 15f535f3d6..39cb9395ab 100644
--- a/test/prism/ruby/ripper_test.rb
+++ b/test/prism/ruby/ripper_test.rb
@@ -81,6 +81,16 @@ class RipperTest < TestCase
       define_method("#{fixture.test_name}_lex") { assert_ripper_lex(fixture.read) }
     end
 
+    def test_lex_ignored_missing_heredoc_end
+      ["", "-", "~"].each do |type|
+        source = "<<#{type}FOO\n"
+        assert_ripper_lex(source)
+
+        source = "<<#{type}'FOO'\n"
+        assert_ripper_lex(source)
+      end
+    end
+
     module Events
       attr_reader :events