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Memory Alpha
File:San Francisco attacked2.jpg

Starfleet Headquarters in ruins following the Breen attack.

File:Sanfranciscoraid.jpg

Breen ships over San Francisco.

The Raid on San Francisco was a surprise attack against Earth launched by the forces of the Breen Confederacy in late 2375. Although most of the attacking Breen warships were destroyed by Starfleet defenses, the raid caused massive damage to its intended target of Starfleet Headquarters, the city of San Francisco and the Golden Gate Bridge.

The attack was a major blow to Federation morale and an equally major boost to the power of the Dominion. This bold military stroke marked the Breen's entry into the Dominion War. Klingon General Martok remarked on the daring of the act, saying "even my people never attempted that." (DS9: "The Changing Face of Evil")

This attack may be the first successful one to occur in nearly two centuries at that point. Dialogue in "Homefront" and "Paradise Lost" suggests that the last such occasion was during the Earth-Romulan War.

Several days later, Chief Miles O'Brien cited the attack as being responsible for Commander Hilliard's odd behavior towards Doctor Julian Bashir. (DS9: "When It Rains...")

The damage caused by this attack was repaired by 2376. (VOY: "Pathfinder")

It should be noted that, considering the massive planetary damage done by the Romulan-Cardassian fleet at the Battle of the Omarion Nebula and the damage it was said that a Constitution class starship was capable of even in the 23rd century, it seems likely that the largest Breen warships were stopped by Starfleet before they reached Earth, or much more massive damage would probably have occurred.
The relatively limited damage shown suggests that smaller Breen fighters or atmosphere-capable spacecraft were the actual attackers of the city. It is also likely that, given Earth's vital importance to the Federation, the planet would have significant orbital defenses.
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