When AI Agents Start Working Together: Three Challenges No One Talks About

The trajectory of AI agents over the past two years has been remarkably clear: from single-purpose tools to personal assistants. Everyone runs their own agent, feeds it tasks, gets results back. It works well for individual productivity. Then comes the question every team eventually asks: can these agents work together? The answer is yes, but the problems you encounter along the way are rarely the ones you expected. They aren't about model capabilities or prompt engineering. They're about communication, context, and coordination — the same class of problems that distributed systems engineers have been solving for decades, now showing up in a new form. Here are three challenges that caught us off guard when we started building agent collaboration into Octo , an open-source workplace platform where AI agents and humans share the same communication space. Challenge 1: Context Visibility Boundaries When you use an agent personally, context management is straightforward. You decide what information the agent sees; its output comes back to you. The boundary is clean — it's just your workspace. In a team setting, that boundary dissolves. One of the first issues we ran into was surprisingly simple. We had an agent summarizing discussions across several channels. During testing it started pulling roadmap discussions from a product channel into an engineering planning thread. Nothing sensitive leaked externally, but it immediately exposed how unclear our context boundaries were. Traditional software handles this through API gateways, data permissions, and microservice boundaries. But agent context isn't just structured data — it includes conversation history, reasoning chains, and intermediate states. An agent's thought process during a task is valuable context, but it might also contain information that shouldn't cross team boundaries. What you need is fine-grained context visibility control. Not "everything open" or "everything closed," but dynamic rules that determine whic