There's no flagging system, at least not yet. It is all luck of the draw for now, though as I say a very large dollar value item like the pipe will almost always result in taxes being assessed. I try to keep the value of any orders down below about $400CAD to keep them from snooping, but as I say it still results in getting "caught" about 35% of the time.Yes that's the dispute I filed and I got it reduced to $900 with my explanation. Now I don't think that this is all entirely accurate or makes sense to me and I'll tell you why... For cigars, If I'm home when they try to deliver I have been able to get the goods and pay nothing, no Duty. But if I'm not home that's when it gets sent to the post office and they file the paperwork and I get hit with Duty. For pipes, never really had an issue until now with this Jess Chonowitsch, had to pay $1050 Duty. I don't know what will happen to the next ones, maybe I'm now flagged with red signals all over.. I'll find out soon enough. I work for the government too so I never want to break any laws but I sure wish Duty wasnt so crazy here...
Until tobacco is made illegal to import or own you're not breaking any laws. Its the CBSA's job to assess the taxes, if they miss your package its not your problem - its theirs!