Time flies when you are having fun, but it's less clear what velocity the years move when you're in the shadow of a colossal bummer. Legal tech isn't all sunshine and daffodils, and over the course of the last decade, the industry and its players have faced some tremendous challenges. The gamut runs from internal strife all the way down to some truly troublesome ransomware. But perhaps the biggest hurdle providers have faced is technology itself, which occasionally seems to present as many problems as it solves. Here's a look at some of the more pressing issues that legal tech companies have faced over the past decade.