Americans who were unable to enroll in federal Obamacare insurance plans over the weekend because of computer glitches or long waits will have until Sunday, Feb. 22 to sign up, federal officials announced. Feds extend Obamacare enrollment period for some Americans who were unable to enroll in federal Obamacare insurance plans over the weekend because of computer glitches or long waits will have until Sunday, Feb. 22 to sign up, federal officials announced.