This article shows that for two years prior to the June 1967 Six-Day Mideast War, Soviet-Egyptian relations had begun to fray because the Soviet Union wanted to loosen its ties with radical regimes in the Third World, including Gamal Abdel Nasser's Egypt. Soviet leaders urged Nasser to reform the Egyptian economy, decrease Egypt's military involvement in Yemen, and allow the Soviet Navy unfettered access to Egyptian ports. But like numerous other small powers during the Cold War, Egypt was able to fend off the pressure of its superpower ally. In May 1967, when Egypt unilaterally decided to bring its forces into the Sinai, Soviet leaders were divided over how to respond to the crisis that engulfed the Middle East. In the end, the more cautious faction in Moscow prevailed, and the Soviet government continued to be wary of becoming embroiled in conflicts initiated by radical Third World regimes.