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A /27 range of IP Addresses inside my /24 Subnet in Azure vNet isn't working

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If I assign to a VM... It works without issue, but if I try using .96 thru .127 (aka CIDR) then I can no longer access the VM directly (only via a jump box on the same subnet as the VM) and the VM cannot reach anything outside the subnet (including DNS servers, or other VMs in peered vNets).

Has anyone seen this happen in Azure before? I checked all the NSG/UDR settings I could find, and already filled a support ticket, but this is driving me crazy!

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