Extension of period of stay only 5 days left

I have an existing residence status which allows me to stay in Japan until May 27, 2016. I want to extend or renew my resident status for another year but according to the immigration website I can only do so 3 months before my stay period expires (Feb 27).

The problem is I will go on vacation in the Philippines from March 7-May 22. I already have my tickets booked :(. If I will submit my application for extension of period of stay on Feb 27, I will be forced to cancel my vacation because processing takes around 2 weeks to 2 months. So I decided that I will just submit once I get back which is on May 23. My concern is that, will I still be allowed to enter Japan on May 22 given that I only have 5 days left before my period of stay expires?

I have no problems with the documents needed for the extension because I work for a company and they will hep me get the documents required. I am just a little bit afraid that I might not be allowed to enter Japan on May 22.

Any response would be greatly appreciated. Thank you

No problem to reenter and extend when you get back. Plus the rules allow you to stay in Japan while your application is processing.

Alternatively, you could theoretically apply before hand as most simple renewals are processed within a week or two. If it isn't processed in time you can halt the application and reapply when you return.

I extended my status once with an international trip looming once as well, and asked immigration specifically what to do if I didn't get the extension in time. They said it was no problem for me to leave the country and come back during the application period. I would suggest going to immigration when you can and just explain the situation. They will give the best advice and can tell you which is better to do.

The only issue arises if your application is approved while you are gone. In that case you have something like 2 weeks to update your passport, and if you miss the window you may have to reapply for the renewal from scratch. Not a major deal, but a likely situation if the OP is gone for a 2.5 month period.

If you apply at the end of February you'll still have a month before your trip, which should be plenty of time for your renewal to process.

True, but I've also missed that window before (the little postcard was delivered but got lost under my shoe cabinet, so it was almost a month later when I went in) and no questions were asked, they just did it. Not saying that is what will happen when you miss it, just saying that going to talk to immigrations your best bet IF you're that worried about it, just because they'll have the best advice for you. But just follow yllwsmrfs advice and you'll be fine!