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People are strongly advised to pay taxes due, regardless of how old they may be.

But wouldn't it seem obvious that paying taxes due years back would be somewhat of an admission of guilt? You are technically required to pay taxes when due -- so anything after that is already bad.

How is one supposed to go about, say, paying years of past due taxes without in some way clearly spelling out that they've been skipping out? Would that itself raise any red flags/point out legal issues?

I know of late fees and such, but to what end is it a "late fee" vs. "imprisonment for tax evasion?"

It could been seen as ill-advised to come forward & pay dues if you know you'll get imprisoned for it when attempting to rectify the issue, rendering the whole subject to that of a land mine approach. If forgiveness is guaranteed then it makes sense, but otherwise some folks might prefer to be outlaws.

Of course I'm looking at this both legally to the core; and of motives that one might most benefit from.

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Would that itself raise any red flags/point out legal issues? to what end is it a "late fee" vs. "imprisonment for tax evasion?"

A taxpayer's voluntary payment/filing of overdue taxes is very unlikely to lead to imprisonment or prosecution. Here voluntary means that the tax department (example: IRS in the US) did not even have to allocate resources for auditing and taking the taxpayer to court.

Furthermore, going after the voluntary taxpayer would discourage others from trying to mend their evasion. That will contravene the interest of any tax agency, which ultimately is to collect revenue efficiently.

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