Went to CW today. The immigration lady confirmed that the online system only checks your last successful report date. If you travel abroad, she said you need to do your next reporting in person because the online system can’t detect the entry date.
However, some people on the forum have had luck by putting in the reporting due date prior to exiting the country and it worked for them, but might not work for everyone and not sure if it can be trusted.
Good luck guys…