H1-B extension solely for recapturing vacation time

[VivekG]

My H1-B visa, I-797 and I-94 ends on Aug 23, 2018. I recently went on a vacation for 5 weeks and hence my 6 year maxout is on Sep 28, 2018. I don't have any plans to stay even a day longer. Can I apply for extension (normal processing) and stay here for those 5 weeks? 

If USCIS takes my extension (normal processing) a little later, say by Oct 2018, will they reject the extension because maxout is over? In that case, will they consider my stay from Aug 23 - Sep 28 as illegal? Or will they just abandon my extension processing request?

If my extension is put in RFE between 8/23 and 9/28, I will not have sufficient time for re-submission. In this scenario, what will I have to do? Will they consider my stay from Aug 23 - Sep 28 as illegal?

If my extension is put in RFE after my maxout and departure on 9/28, what should I do? What are the consequences? Will my stay be considered as illegal?

[satya2k1]

When your employer requests for extension, they should submit the basis for their request.  If it is purely recapturing time that you were not present in the USA, then you have to provide evidence that you were not in country for those 5 weeks. 

Most probably, the USCIS will deny your H1B if they adjudicate your petition.  Because, if your employer submit your H1 application now, it takes atleast 3 to 4 months to get adjudicated, which means around October 15th, by that time your 5 weeks recapture is also done.

If USCIS takes my extension (normal processing) a little later, say by Oct 2018, will they reject the extension because maxout is over? In that case, will they consider my stay from Aug 23 - Sep 28 as illegal? Or will they just abandon my extension processing request?  You have to leave the country immediately even before you get a Notice to Appear.  As per new policy, USCIS will issue a NTA when petitions are denied.

If my extension is put in RFE between 8/23 and 9/28, I will not have sufficient time for re-submission. In this scenario, what will I have to do? Will they consider my stay from Aug 23 - Sep 28 as illegal?   Less chances of getting RFE between 8/23 and 9/28, if you do, and you don't have enough time, then you have to leave the country immediately.  Regarding illegal stay, it depends on how you convince the office at the time of re-entry, you need to have solid proof that you did not stay illegally.

If you do not have any intention of staying after H1B, then why would you risk the future entry? If you leave on time, then you will save money and also no risk when you come back next time.