Job Overlap Prohibition (Japan -> Overseas)

I will be leaving my current job for a job overseas. I made the mistake of oversharing my start date to my new job. I have more than a month’s worth of leaves that I planned to use, which would result in an overlap of 1 month with my now job. Current manager says they don’t allow double employment even if I am just using terminal leave, and even if the next company is not in Japan.

Also, they want me to set my last day on the end of months only and not any other day of the month. If I don’t overlap my leaves with my new job start date, then I would be looking at 1-2 weeks without health insurance until my new one overseas kicks in, unless I do a lot of leg work just to be covered for those 1-2 weeks.

My questions are:

1. Do I just do a wink wink oh my new start date is aaachutallly later than I thought? Or are there things I need to do by being physically present in Japan/my company on my actual last day? i.e. returning insurance card etc.
2. Is this end of the month requirement for last day of work typical?
3. What’s the best way to stay insured within the 1-2 weeks gap between my employment?

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I have PR if that makes a difference.

by espadrillies

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