When Japan assumed control of Taiwan in 1895, the first governor-general set up temporary quarters in a former Qing dynasty secretariat. Plans for a permanent headquarters began almost immediately. A two-stage architectural design competition was held in 1906 and 1910, and the winning entry by architect Uheiji Nagano blended Renaissance, Baroque, and neoclassical European elements with the colonial tradition of east-facing facades. Tokyo authorities revised Nagano's plans before construction began, increasing the central tower from six stories to eleven and adding defensive improvements to the corner towers. Construction started on June 1, 1912, and finished on March 31, 1919, at a cost of 2.8 million Japanese yen. The finished building became one of the most recognizable structures in colonial Taiwan.

On May 31, 1945, during the Allied Raid on Taihoku, bombs struck the front left side, main lobby, and northern sections of the Governor-General's Office. The resulting fire burned for three days, gutting large portions of the building. Forty-five days later, Japan surrendered. The ruin sat untouched until 1947, when the Taiwan Provincial Government launched a restoration funded entirely through private donations. Approximately 81,000 workers participated in the reconstruction, which was completed by the end of 1948. The restored building looked only slightly different from the original -- most notably, the ornate Baroque entrance hall was rebuilt with simpler interior features. Because the restoration coincided with Chiang Kai-shek's 60th birthday, the building was renamed Chieh Shou Hall, a name it carried until 2006.

In mid-1949, as the Chinese Civil War turned decisively against the Nationalists, the building began serving as a military affairs office. When the Republic of China government relocated its capital to Taipei, the structure became the Office of the President in 1950. The transition was more than administrative -- it transformed a colonial building designed to project Japanese imperial authority into the symbolic center of a Chinese government that no longer controlled the Chinese mainland. The Nationalists built a platform atop the central tower for martial flag-raising ceremonies, overlaying their own political rituals onto the Japanese architectural framework below. Former President Chen Shui-bian later revealed that a hidden tunnel connects the building to the Shilin Official Residence, adding a layer of Cold War intrigue to an already densely storied structure.

Today the Presidential Office Building occupies the city block between Chongqing South Road and Bo'ai Road, its 130-meter-wide facade commanding the full width of Ketagalan Boulevard. The west gate features a grand marble staircase lined with Ionic and Corinthian columns. The office wings contain balconies and long corridors overlooking the sunlit North and South Gardens. Within walking distance stand the Judicial Yuan Building, 228 Memorial Park, the National Taiwan Museum, the National Theater and Concert Hall, and the historic Ximending shopping district. In 2019, the building opened its doors to international overnight guests through a program called "Spend A Night at Taiwan's Presidential Office Building," selected participants from eleven countries sleeping inside a structure that has sheltered colonial governors, wartime commanders, and democratically elected presidents. The program ran again in 2023, a gesture of openness from a building long associated with guarded power.