A read-ahead mechanism is provided for a redirected Bulk-In endpoint of a USB device. When a USB device is redirected to a server, an agent running on the server can evaluate the USB device's descriptors to determine whether it has any Bulk-In endpoints and whether any Bulk-In endpoint is part of a mass storage interface. For any Bulk-In endpoint that is not part of a mass storage interface, the agent can create a circular buffer and commence originating bulk read requests on the server and then redirecting the bulk read requests to a client-side proxy for delivery to the Bulk-In endpoint. The agent can then store the data it obtains from these bulk read requests in the circular buffer. By repeatedly sending the bulk read requests to the Bulk-In endpoint, the agent ensures that data will be read from the Bulk-In endpoint in a timely manner.