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There is no point at which it becomes OK if that is what you mean. If you don't file you are perpetually open to audit and assesment for that period. (The statute that regulates how long you can be questioned about your filing starts running from the time it is filed...don't file and it never starts or ends). You can get automatic extensions for filing (NOT FOR PAYING...you do that by estimate when askling for the extension on when to file), starting with the date they are due.

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Q: What is the cut off for not filing taxes?
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