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If I go hybrid, will I need to request for two licenses (cloud and on-premise)?
If you are running a Lansweeper On-prem you will have the ability to link your On-prem to the Lansweeper Sites without having to purchase an additional license for the Cloud environment. The following article might be helpful for this process:
https://community.lansweeper.com/t5/sites/link-lansweeper-on-prem-with-lansweeper-sites/ta-p/64514