While it is commonly accepted that maintaining common ground plays a role in conversational success, little prior research exists connecting conversational grounding to success in task-oriented conversations. We study failures of grounding in the Ubuntu IRC dataset, where participants use text-only communication to resolve technical issues. We find that disruptions in conversational flow often stem from a misalignment in common ground, driven by a divergence in beliefs and assumptions held by participants. These disruptions, which we call conversational friction, significantly correlate with task success. We find that although LLMs can identify overt cases of conversational friction, they struggle with subtler and more context-dependent instances requiring pragmatic or domain-specific reasoning.