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The resource landscape for high energy physics experiments in the HL-LHC era is expected to be more dominated by Cloud and HPC rather than traditional Grid sites, reaching scales much higher than current capacity. HPC and Cloud resources are much more diverse and heterogeneous than traditional Grid resources, each with special capabilities or limitations that must be handled by the submission infrastructure. The CMS experiment at the LHC at CERN is actively focusing on the functionality necessary to adapt the HTCondor infrastructure to fulfil these needs and requirements, with enhanced customization and control over resource allocation and usage while maintaining global flexibility. The stability and scalability of HTCondor pools to HL-LHC scales is thought to be tractable, with the increasing complexity of the pool architecture driving limitations.