A system for scheduling transmission times to avoid connection timeouts includes a memory configured to store data in a buffer for upload to a storage system. The system also includes one or more computing devices configured to implement a connection manager. The connection manager is configured to establish a connection to a storage system. The connection manager is configured to iteratively repeat, until the data transfer operation is completed, begin transmitting the data from the buffer via the connection to the storage system, stop transmitting the data from the buffer via the connection to the storage system, where at least a portion of the data is retained in the buffer, determine a time to resume transmitting the data from the buffer via the connection to the storage system to avoid a connection timeout for the connection to the storage system, and wait until the time to resume.