The close relationship between clients and outside counsel has survived the invention of the letter, the proliferation of telephones and the heartbreak of an overflowing email inbox. But the sheer volume of new communication methods—from text messages to chat platforms to video conferencing tools—may push for a reexamination of this relationship's dynamic. For starters, while it's never wise to say "no" to the boss, law firms may have to take a firmer hand in guiding clients away from the convenience of a text message and toward more secure means of communication. In turn, corporate legal departments may have to adapt to a reality where outside counsel can be reached around the clock, but also begin putting up firmer boundaries to keep from burning out. The biggest turning point may not arrive until after the COVID-19 pandemic has been resolved. In-house teams who have grown used to working remotely might have to decide whether the comforts of working from home outweigh the intimacy that can be gained by working face-to-face. Above, we look at five challenges that communications tools pose to in-house relationships with outside counsel.