It's not obvious indeed! The idea is to; 1. take out the ring (try it by releasing the back part first! easy does it. 2. put tape into the Dymo 1855 mk II by pressing the white lever down 3. then take the tape you pushed through and guide it through the ring. 4. Put the ring back into the Dymo.
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Dual cassette deck are often poorly built and full of problem with age. They are typically not worth repair. Get a good deck like the Tascam 122 Mk II as these can be repairs.
I have consulted with clients that have dual decks and the cost to repair will get you a Tascam 122 Mk II in restored condition and it works much much better. I should know as I have been repairing decks for 40 years so far.
I was having the same problem. When you load the tape make sure to push it through the slot just in line with the white lever that sticks out of the left side of the machine.
I have one of these and there is a white sliding button on one of the broad sides of the labelmaker. It slides from 3/8 inch to 1/4 inch. It is located toward the top right. It's NOT the side with the letter wheel but the opposite side. If yours doesn't have t his button, it probably won't take two sizes of tape. (But I'd be surprised if it didn't have the button.) Hope you find it.
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