diff --git a/parse.y b/parse.y
index 07be7e9907..a0ed61f80b 100644
--- a/parse.y
+++ b/parse.y
@@ -9036,7 +9036,7 @@ here_document(struct parser_params *p, rb_strterm_heredoc_t *here)
         if (!has_delayed_token(p)) {
             dispatch_scan_event(p, tSTRING_CONTENT);
         }
-        else {
+        else if (p->delayed.end_line + 1 == p->ruby_sourceline) {
             if ((len = p->lex.pcur - p->lex.ptok) > 0) {
                 if (!(func & STR_FUNC_REGEXP)) {
                     int cr = ENC_CODERANGE_UNKNOWN;
@@ -9051,6 +9051,10 @@ here_document(struct parser_params *p, rb_strterm_heredoc_t *here)
             }
             dispatch_delayed_token(p, tSTRING_CONTENT);
         }
+        else {
+            dispatch_delayed_token(p, tSTRING_CONTENT);
+            dispatch_scan_event(p, tSTRING_CONTENT);
+        }
         lex_goto_eol(p);
 #endif
         heredoc_restore(p, &p->lex.strterm->u.heredoc);
diff --git a/test/ripper/test_lexer.rb b/test/ripper/test_lexer.rb
index a371e8c42d..7a2c22ff2d 100644
--- a/test/ripper/test_lexer.rb
+++ b/test/ripper/test_lexer.rb
@@ -344,6 +344,47 @@ world"
     ]
 
     assert_lexer(expected, code)
+
+    code = <<~'HEREDOC'
+      <<H1
+      #{<<H2}a
+      H2
+      b
+    HEREDOC
+
+    expected = [
+      [[1, 0], :on_heredoc_beg, "<<H1", state(:EXPR_BEG)],
+      [[1, 4], :on_nl, "\n", state(:EXPR_BEG)],
+      [[2, 0], :on_embexpr_beg, "\#{", state(:EXPR_BEG)],
+      [[2, 2], :on_heredoc_beg, "<<H2", state(:EXPR_BEG)],
+      [[2, 6], :on_embexpr_end, "}", state(:EXPR_END)],
+      [[2, 7], :on_tstring_content, "a\n", state(:EXPR_BEG)],
+      [[3, 0], :on_heredoc_end, "H2\n", state(:EXPR_BEG)],
+      [[4, 0], :on_tstring_content, "b\n", state(:EXPR_BEG)]
+    ]
+
+    assert_lexer(expected, code)
+
+    code = <<~'HEREDOC'
+      <<H1
+      #{<<H2}a
+      H2
+      b
+      c
+    HEREDOC
+
+    expected = [
+      [[1, 0], :on_heredoc_beg, "<<H1", state(:EXPR_BEG)],
+      [[1, 4], :on_nl, "\n", state(:EXPR_BEG)],
+      [[2, 0], :on_embexpr_beg, "\#{", state(:EXPR_BEG)],
+      [[2, 2], :on_heredoc_beg, "<<H2", state(:EXPR_BEG)],
+      [[2, 6], :on_embexpr_end, "}", state(:EXPR_END)],
+      [[2, 7], :on_tstring_content, "a\n", state(:EXPR_BEG)],
+      [[3, 0], :on_heredoc_end, "H2\n", state(:EXPR_BEG)],
+      [[4, 0], :on_tstring_content, "b\nc\n", state(:EXPR_BEG)]
+    ]
+
+    assert_lexer(expected, code)
   end
 
   def test_invalid_escape_ctrl_mbchar