The baristas at three corporate-owned Starbucks stores, to date, have voted for union representation, and workers at more than 100 more stores in 19 states have filed for Labor Board elections. To slow the pace of new elections, Starbucks has enlisted a massive legal team. But the coffee chain suffered a tough legal setback in February, thanks to some late emails.

Through its lawyers from the firm Littler Mendelson, Starbucks asked the National Labor Relations Board not to move ahead with some of the votes, arguing that elections for individual stores aren’t appropriate. The company wants all the stores within the region grouped into one big vote. Sadly, that argument has slowed down the legal process and bought Starbucks more time to run its campaign against the union. But the strategy ran aground in New York when Microsoft Outlook apparently crashed on Starbucks’ lawyers.

In order to make its case for the bigger union election, Starbucks had to submit what’s known as a Statement of Position to the labor board and the union by noon on Feb. 11. The company’s lawyers apparently didn’t get all the paperwork to the union’s lawyers until 12:08 p.m.

The lawyer from Littler Mendelson explained the mishap in a filing to the labor board, saying the files attached to the emails were apparently too large and crashed. Ian Hayes, a Buffalo-based labor lawyer working for Starbucks Workers United, argued that the company shouldn’t be allowed to make its case because of the blown deadline.

The labor board sided with the union, saying that “the employer’s failure to timely serve its Statement of Position precludes it from litigating any of the issues raised in its untimely submission.” Starbucks is expected to appeal the ruling because delaying elections allows them more time to persuade workers to vote against the union.

The legal tussle is the latest indication of how the gloves have come off between Starbucks and Workers United. The union says the company’s legal case against single-store elections is a redundant waste of time. Starbucks has made essentially the same argument against each new election effort, but so far, labor board officials have knocked it down at each turn.

None of Starbucks’ roughly 9,000 corporate- owned stores had union representation until late last year when the union won two out of its first three elections in New York. A third election, in Arizona, was also recently won.

By Dave Jamieson, Huff Post