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In what circumstances can you go to jail for not paying taxes in the US/UK?

For instance the company doesn't pay taxes for very long time and government can't take any money from the company. Is it different whether it's sole-trader or sole-member LTD/LLC company?

4

A special case is not paying the income tax that the company is supposed to be paying on behalf of its employees. If an employee makes £4,000 a month, and the employer is supposed to pay £1,000 tax and doesn't, that's not the employer's money, that's the employee's money. Not paying the employee's money is a much more serious matter than not paying your own taxes.

A google search found this article http://www.gaebler.com/Not-Paying-Payroll-Taxes.htm which says that a person not paying taxes for employees is personally liable, that this liability does not go away with bankruptcy, and that jail is possible.

So their advice is: Whatever other debt you have, paying taxes for your employees' payroll is the absolutely highest priority (higher priority than paying wages, paying the rent, paying company taxes and so on).

3

First, in both the US and the UK there are criminal sanctions including prison terms for breaching tax laws; Al Capone being the most famous example.

This is not the same as legitimately following the tax laws and then being unable to pay when required.

A person (including a corporation) who is unable to pay their debts (which includes taxes) as and when they fall due is bankrupt. There are laws that deal with bankruptcy and they also have criminal sanctions including prison if you don't follow them. However, if you do follow the law then you cannot be sent to jail for being bankrupt.

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