A method for network-connected tool operation with user anonymity includes generating a first cryptographic key that is stored in a memory in the power tool, generating a first encrypted serial number for the power tool based on an output of an encryption function using the first cryptographic key applied to a non-encrypted serial number for the power tool stored in the memory, and generating usage data based on data received from at least one sensor in the power tool during operation of the power tool. The method further includes transmitting the usage data in association only with the first encrypted serial number from the power tool to a maintenance system to enable usage data collection that prevents identification of the power tool as being associated with the usage data.