Emerging cloud services, including mobile offices, Web-based storage services, and content delivery services, run diverse workloads under various device platforms, networks, and cloud service providers. They have been realized on top of SSL/TLS, which is the de facto protocol for end-to-end secure communication over the Internet. In an attempt to achieve a cognitive SSL/TLS with heterogeneous environments ( device, network, and cloud) and workload awareness, we thoroughly analyze SSL/TLS-based data communication and identify three critical mismatches in a conventional SSL/TLS-based data transmission. The first mismatch is the performance of loosely coupled encryption-compression and communication routines that lead to under-utilized computation and communication resources. The second mismatch is that the conventional SSL/TLS only provides a static compression mode, irrespective of the dynamically changing status of each SSL/TLS connection and the computing power gap between the cloud service provider and diverse device platforms. The third is the memory allocation overhead due to frequent compression switching in the SSL/TLS. As a remedy to these rudimentary operations, we present a system called an Adaptive Cryptography Plugged Compression Network ( ACCENT) for SSL/TLS-based cloud services. It is comprised of the following three novel mechanisms, each of which aims to provide an optimal SSL/TLS communication and maximize the network transfer performance of an SSL/TLS protocol stack: tightly-coupled threaded SSL/TLS coding, floating scale-based adaptive compression negotiation, and unified memory allocation for seamless compression switching. We implemented and tested the mechanisms in OpenSSL-1.0.0. ACCENT is integrated into the Web-interface layer and SSL/TLS-based secure storage service within a real cloud computing service, called iCubeCloud, as the key primitive for SSL/TLS-based data delivery over the Internet.