A few months have passed since organizations have adopted remote work at scale. And although many people have highlighted the benefits (e.g., reduced commute time) of this work arrangement, many have also underscored the downside. This article highlights how the challenges of remote working are becoming more apparent as the coronavirus pandemic persists. These pitfalls range from 1) projects taking longer to complete, 2) workers appearing less connected, 3) diminished quality of work 4) concerns that younger professionals aren’t developing at the same rate as they would in offices, 5) challenges to collaborating, 6) obstacles to hiring and onboarding new workers. While technological innovation will help to overcome these challenges, it is essential to recognize that the pro vs. con debate of remote working is heavily influenced by a) a matter of preference – some people simply desire to be in the office, and others don’t b) personal home situation – work from home environments may not be conducive to productivity c) culture – some organizational cultures operate in ways that make remote working easier d) work – some jobs are more conducive to this arrangement. These factors should be considered as organizations continue to develop solutions that enable effective remote working.