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The low pressure port is the one that your A/C re-charge kit fits. The high side has a similar, though different, fitting. You can't guess wrong...it won't fit wrong.
Legally in most states the system must be checked for "detectable leaks" before servicing. If the system has been opened, airlines disconnected etc... the drier should be replaced as it quickly does its job of absorbing moisture in the air. The system then needs to be placed in a vacuum and all moisture removed from system, this is also how to check for leaks. If it passes to this point then you can properly insert the proper amount of refrigerant in the system. This is just a quick synopsis of servicing a typical a/c system that is in good, working condition. There is much more to it and you also need the proper gauges and tools, and knowledge to do it your self. These Walmart kits that you just go home and plug it in are just a joke. You have no idea od anything about your system.
Given the inherent dangers of accidently tapping into the high side, and knowing how refrigerant and oil can behave, the above statement is spot on. BTW, you should already have your safety glasses on.