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Law firm technology directors, it would seem, just aren’t destined to get a good night’s sleep. First there was the recession, which slowed the pace of upgrades and new projects. Then there were lawyers using their personal smartphones and tablets for work, raising questions about how firms should safeguard data on those devices. Now, a new challenge is keeping restful slumbers at bay: Protecting against cyberattacks—and convincing clients that the firm is doing this job well.