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Short answer to your question is yes, part of an Invisalign button aka attachment can break off, in which case it should be repaired. However, many attachments in use today do not fill the aligner form fully, to allow for concentrated force delivery, and room for movement. Your doctor can tell you what the situation is in your case.
It’s possible for an attachment to wear out or partially break of over time. Depending how far along you are in treatment your doctor might choose to not replace it. If the tray is not sitting in all the way that might also cause the attachment not fully fill in the mold.
It is indeed possible for a button to partially break. If you are midway or partway through your treatment and need a button replaced, your doctor may have to order an attachment template from invisalign that correspondes to the tray number you are now using. This can take a couple of weeks.
If your overbite is that extensive Invisalign might not be the best option. It would only be able to decrease the overbite slightly so it really depends on what your end goal is. They would also have to evaluate if tooth extraction is an option to fully correct the overbite.
You can certainly get your cavities filled while you are in aligners. Given this situation, I normally fill one or two cavities at a time to make sure aligners still fit properly afterwards rather than filling them all at once.
If they weren't included in your treatment then you can expect to pay $500-$750 in most areas. $1100 does seem a little high. You can go to any Invisalign dentist to get Vivera retainers.