At the onset of the revolution, and in response to reports of "successive triumphs" in Cavite, some

3,000 revolutionary forces marched to seize the town of Paombong, Bulacan, forming a military
government. Del Pilar was among those who marched towards Paombong, although there are also
rumors of him being present during the Cry of Balintawak.[3]
Del Pilar was eventually assigned to the forces of Eusébio Roque (also known as Maestrong Sébio)
in Kakarong de Sili, a fort near the town of Pandi. On New Year's day, 1897, del Pilar participated in
the defense of Kakarong de Sili, managing to escape with only nine others before the Spanish
overran the fort. He recounts in his diary:[3]
"As for me, I need not say how I fought. Those who saw me in peril can tell. A Mauser bullet grazed
my forehead. Thank God I was spared that danger. Finally, I had to leave the fort because, when I
looked for our valiant brothers, none was any longer at his post. This should not cause shame. Self-
preservation is the law of God. I passed the night in the barrio of Manatal."

— Gregorio del Pilar, Recounting his 'baptism of fire' and escape during the Battle of Kakarong de
Sili.
His courage and bravery in that action won him recognition and a promotion to the rank of lieutenant.
[6]
 He eventually left Roque's unit - Roque was sold out to the Spanish by his own soldiers and
executed in February 1897, and del Pilar began to make his way to Imus, Cavite, reaching as far
as Montalban in February. He eventually returned to Bulacan and joined Adriano Gatmaitán's army,
being promoted to captain in the process.[3]
As captain, del Pilar managed feats of bravery. He once managed to single-handedly ambush a
priest and his escort of cazadores from Mambog on their way to Malolos. He shot one of the
cazadores which prompted the rest to flee.
The event is termed as "pinagtambangan," according to the marker that can be found on Malolos
Bridge.
This act netted him several Mauser rifles and four sacks of coins, which he distributed to his troops.
He decreed that married men be given 50 pesos each, unmarried ones 25 pesos, and the remaining
money be sent to Manila to buy a blanket and a cloak for each soldier. [5]

Flag of Gregorio del Pilar

On September 3, 1897, del Pilar executed an attack on the Spanish garrison in the town
of Paombong. He and ten other men slipped into town in the night and fell upon the cazadores in the
basement of the convent during Sunday mass. Del Pilar himself was stationed in the plaza, firing at
the second story of the convent to prevent any men from approaching from the windows. They were
eventually able to capture 14 Mauser rifles. Other versions of the raid vary, however. Some tellings
talk about how del Pilar and his men slipped into town dressed as women, while other versions have
them disguised as cazadores.[3] Del Pilar's success in Paombong caught the attention of Emilio
Aguinaldo, who promoted the captain to a lieutenant colonel, eventually earning his trust and being
let into his inner circle of confidants. Artemio Ricarte noted that Del Pilar's feat in Paombong “exalted
him to the horns of the moon."[7]
Del Pilar celebrated his promotion to lieutenant colonel by creating a distinctive flag for himself and
his battalion: a tricolor with a blue triangle at the hoist, red stripe on top and black at the bottom,
taking cues from the Cuban flag. He first unfurled this flag during his participation in the Battle of
Pasong Balite (modern-day Polo, Bulacan) in 1897.
Due to his closeness to Aguinaldo, del Pilar became one of the signatories of the provisional
constitution of the Republic of Biak-na-Bato in November 1897. When negotiations with the Spanish
took place in the which concluded with the signing of the Pact of Biak-na-Bato, Aguinaldo took del
Pilar with him to exile in Hong Kong