It was also the second such strike against U.S. and Afghan targets in and around Kabul since American commanders officially handed over security operations in the country to local forces last Tuesday.
Seven people were killed in the unsuccessful attack, but not before Taliban fighters disguised as ANSF soldiers were able to detonate a massive car bomb inside the presidential compound, recent reports states.
The daytime assault on the Afghan presidential palace underscores the terror group's willingness to take the fight into the Afghan capitol in recent months.
In May, Taliban fighters kicked off this year's fighting season in the country by blowing up an American convoy traveling through through the capitol, killing 16 people including six American military advisers.
The bombing was the first major strike against U.S. and coalition targets inside Kabul since last February.
Earlier this month, Afghan military and police repelled a coordinated Taliban attack against the main airport in Kabul, ending with the deaths of seven insurgents.
Waves of Taliban gunmen and suicide bombers assaulted the airport, looking to breach the military side of the facility that serves as headquarters to International Security Assistance Force (ISAF) Joint Command.
At no time was the ISAF side of the airport breached, and no American or NATO troops were killed in the ensuing gun battle, a command official said at the time.
Days after the airport attack, Taliban insurgents detonated a massive car bomb in downtown Kabul in an apparent attempt to kill members of the country's supreme court.
Roughly 17 civilians were killed and 40 were critically wounded when the explosive-laden sport utility vehicle blew up on a busy intersection near the court's offices.
The U.S. Embassy was also in the blast zone, but Afghan officials claim the diplomatic outpost was not the target of the attack.
Earlier this year, U.S. and coalition commanders warned that singular strikes on high-profile targets in Kabul would be the hallmark of this year's fighting season in Afghanistan.
These types of strikes at the power base of Afghan president Hamid Karzai's government will likely increase as the White House's 2014 withdrawal deadline for U.S. troops in country nears.
Gen. Joseph Dunford, head of all U.S. forces in Afghanistan, expressed concern over Afghan forces' ability to keep the Taliban at bay after the U.S. withdrawal.
"At this point, [U.S. and NATO] have made significant progress, but we are not yet at the point where it is completely sustainable," Dunford said in an interview with the BBC in June.
"That really is the focus of effort over the next 18 months. That's why we need to start now — especially with the Afghan security forces — to talk about 2018, not 2014," the four-star general said at the time.