
Hollingworth had been working as a Telegraph journalist for less than a week when she was sent to Poland to report on worsening tensions in Europe. She persuaded the British Consul-General in Katowice, John Anthony Thwaites, to lend her his chauffeured car for a fact-finding mission into Germany. While driving along the German–Polish border on 28 August, Hollingworth observed a massive build-up of German troops, tanks and armoured cars facing Poland, after the hessian screens concealing them were disturbed by wind. Her report was the main story on the Daily Telegraph's front page on the following day.

Her telephoned reports ignored censorship rules and she is reported to have once avoided arrest by stripping naked. In 1941 she went to Egypt, and subsequently reported from Turkey, Greece and Cairo. Her efforts were hampered by the fact that women war correspondents did not receive formal accreditation.[4] After Field Marshal Bernard Montgomery took Tripoli in 1943, she was ordered to return to Cairo. Wishing to remain at the front lines, she went on to cover General Dwight D. Eisenhower's forces in Algiers, writing for the Chicago Daily News. She subsequently reported from Palestine, Iraq and Persia.[5] During this time she became the first to interview the Shah of Iran.