Transdniestr’s documented history goes back two millennia, when the territory was on the eastern fringes of the Roman Empire. Through the centuries, the territory saw frequent raids by Mongol and Tatar tribes, among others. It was also hotly disputed by Moldavian princes and Ottoman Turks, and later tsarist Russia.

Russia annexed the territory in the 18th century, and Russian influence has been felt ever since. Following WWI, when most of Moldova fell under Romanian control, Transdniestr remained part of the Soviet Union. The territory was only briefly ruled by Bucharest during WWII, when it was overrun by allied Nazi and Romanian troops. Transdniestr played an infamous role during the Holocaust, when Romania’s wartime fascist government transported many tens of thousands of Romanian Jews to death camps here.

After WWII, Transdniestr reverted to Soviet control as part of the Moldovan Soviet Socialist Republic. With the weakening of the Soviet Union in the late '80s and early '90s, and increasing calls by some in Chişinău for closer ties to Romania, officials in Transdniestr became increasingly uneasy. Hostilities broke out between Moldova and Transdniestr in 1992. The fighting lasted only a few months after Russian troops got involved, though hundreds died and the violence shocked citizens across the former Soviet Union.

Since those days, a tenuous peace has reigned. In 2011, long-time Transdniestran leader Igor Smirnov was defeated at the ballot box by Yevgeny Shevchuk. Shevchuk was a reformer who railed against endemic corruption under Smirnov, who was tied to the influential Sheriff conglomerate, which controls most business in Tiraspol. Shevchuk advocated better relations with Moldova, but a true thaw never materialised as pro-Russia sentiment among the public remained strong amid a faltering economy. In 2016, Shevchuk signed a decree confirming Transdniestr's ambitions to join Russia, in line with a 2006 general referendum. Nonetheless, he was soundly defeated at the ballot box in December 2016 by pro-Sheriff, pro-Russian candidate Vadim Krasnoselski of the Obnovlenie party.

Moldova also elected a pro-Russian president, Igor Dodon, in December 2016. Would this lead to a rapprochement between Moldova and Transdniestr? Well, not exactly. Most power in Moldova rests with the parliament, which up until the February 2019 parliamentary elections remained firmly pro-Europe. During 2017–2018 steps were taken to increase integration between the two sides in a few areas – education and transport, for instance. During this time registration rules for foreigners entering Transdniestr also eased.

While these are key steps, true integration rests on the resolution of thornier issues – specifically, the 2006 general resolution calling for independence from Moldova, and the continued presence of more than 1000 Russian 'peacekeeping' troops in Transdniestr. Every year on 29 July, the breakaway republic 'celebrates' another year of the Russian troop presence; 2019 marks 27 long years and counting.