"Break-in" refers to the initial carbonization of the bowl. Many new pipes now come with pre-carbonized bowls that don‘t require a break-in period. I‘d recommend such a pipe for a beginner. However, it‘s desirable to maintain a 1-2 millimeter layer of cake for a cool, even smoke.
If your pipe smokes sour or gurgles, if there‘s a lot of goo inside the stem, or if the cake is very thick, it‘s time for a cleaning. This usually will have to be done every 5-10 smokes. First, use the knife blade of the pipe tool to scrape the cake to the proper thickness. Then use the reamer to get any heavy goo out of the wood part of the air hole of the stummel (the wood part of the pipe). Dip a pipe cleaner in the pipe sweetner, and run it through the stem; repeat with fresh cleaners until they come out clean. Repeat with the stummel air hole; be careful not to get any cleaner on the outside of the pipe, as this harms the finish. After cleaning, let the pipe rest a few hours before smoking it again, to give the sweetner a chance to dry out.
Lastly, enjoy! Pipe smoking should be a pleasurable and relaxing pastime. Don‘t smoke if you don‘t feel like it.
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