The container pouring assist system is a covering for a container that makes the container easier to pour by adding a handle to the bottom rear of the container and a spout to the top of the container. As non-limiting examples, the container may be a heavier container such as a 1 or 2 gallon milk and water container. Using the container pouring assist system the container may be lifted using the container's handle and then tilted using the handle provided by container pouring assist system. The spout may result in a more controlled, more predictable pour. The container pouring assist system may slip onto the container by placing a collar over the neck of the container and passing the base of container pouring assist system under the container until the container seats into the base.