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Most machines require that the bobbin in the case unspool in a certain direction its considered common knowledge I guess because it doesn't seem to be written in the text of manuals... but is indicated in the photos. make sure it's unspooling correctly.
Secondly. Please make sure you have the correct needle for your machine. Some machines do not use a 15x1 (most common needle) Let me show you. (see photo below) Clearly the 241x1 won't fit into your machine. BUT the 15x1 will go into the machine that requires the 20x1.... and the result is it won't pick up the bobbin thread.
The envelopes are standard in size hence do not use any odd sizes. And also do remember that you make the required alignment and also the feeding directions and positions. If you print in Landscape then the paper is too short for the printer to pick. Hence use Portrait so your printer can sense the presence of the envelope
The printer is expecting the label stock to be loaded into the manual feed tray, not the regular paper tray. If it does not sense anything in the manual feed tray it will not continue. If you are loading the stock in the tray, it may need to be pushed further into the try to trigger the sensor.
Most of our printers pull the paper down on one side slightly faster than the other. The printer hardware should even this out when printing. You should also ensure the paper meets the automatic feeder requirements of the printer.
If printing is skewed, feeding multiple pages or jamming, please follow these instructions (use a regular letter size paper to test after doing the steps given below):
Please check to ensure there is nothing obstructing the paper feed mechanism down inside the printer where it is not easily seen. If there is nothing obvious, unplug the printer and remove the paper. Open the front cover and look above the steel rod. You should see a conveyor belt with rubber teeth on it, like a fan belt. Take the bottom part of that belt and move it gently to the left. The cartridges should come out with it. Make sure the cartridges can move fully from one side of the printer to the other. Check also the output rollers on the bottom of the printer for any blockage. If it is jamming under the carrier assembly, you may be able to fix it using the manual feed slot. Turn the printer off. Next take a #10 envelope and feed it through the left side of the paper feed slot (The manual paper feed slot is preferred, but the automatic feed will do if there is no manual paper feed for this printer) until it comes completely through the printer to the back of the exit rollers. Move it up and down and slowly move it over to the right side. If something is stuck under the black guide plate this may work it loose or you may have to feed the envelope through the front rollers and push your way backward (please be careful here).
Next, take a damp warm cloth and clean the rubber rollers in the automatic sheet feeder. Dust may be coating the rollers there and as they become less tacky, they cannot feed paper correctly.