When Your Heartstrings Break is the second album by San Francisco indie rock band Beulah. It was released on March 9, 1999 on the Sugar Free Records label. The album went out of print several years afterwards and did not see a reprinting until 2003. When Your Heartstrings Break is one of the two records that Beulah personally owns the rights to, along with Handsome Western States. The album was released in Japan, Europe and Australia, with each release bearing album art different from the US release.

All songs written by Miles Kurosky, except where noted.

The songs "Sunday Under Glass", "Score from Augusta" and "Emma Blowgun's Last Stand" were released as singles in the United Kingdom on the Shifty Disco label. The song "Emma Blowgun's Last Stand" was released as an EP in Australia on the Elastic Records label. "If We Can Land a Man on the Moon, Surely I Can Win Your Heart" was featured in the 2009 soundtrack to the graphic novel Scott Pilgrim vs. the Universe.

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