Automatic detection of intermediate network device capabilities includes analyzing requests received, at a particular device, from a remote device. The analyzing is performed to determine, based on the content of the requests, whether an intermediate device on the network situated between the device and the remote device does not support streaming of data from the device to the remote device using the pipelining feature of Hypertext Transport Protocol (HTTP) 1.1. In one implementation, a test is performed by sending two back to back requests from the remote device to the particular device. The test is determined to be a success if the requests are received within a threshold amount of time of one another, and a failure if the requests are not received within the threshold amount of time of one another.