can i apply for second extension while first one is still pending ?

[kishireasv]

Need your help friends. My Parents current I94 expired on July 21 2020 and I have applied I539 to extend their stay until August 25th 2020, the application is still pending. Due to their elderly age, I don't want to risk their travel and need to further extend their stay till december 2020. Please help with the below , Thank you very much !

1. Can I file an another I539 application in august while the first application is still pending ?
2. If the second extension request is rejected , will their stay from August until december be considered out of status ?

[newacct]

1. yes
2. They are already "out of status" since July 21. But "out of status" doesn't matter -- they can stay for as long as their I-539 is pending. They will not accrue "unlawful presence" while the first I-539 is pending (or, if the first one is approved, while the second one is pending), even if it is denied or abandoned. If it is denied, "unlawful presence" will only start to accrue from the date of the denial.