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The Benn Act (European Union (Withdrawal) (No. 2) Act 2019) makes it a legal requirement for the PM to ask for an extension from the EU if no Withdrawal Agreement is ratified.

If the PM simply ignores this, say on October 31st, he is in breach of the law.

Or if he resigned immediately before the October 31st deadline, perhaps he would not ever actually breach the law.

What would then happen? There would be no time to do anything before the deadline of the European Union (Withdrawal) Act 2018.

Would that mean the passing of the deadline for that Act would have to be undone retrospectively?

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Text of the Act. Under section 1(3):

If neither of the conditions in subsection (1) or subsection (2) is satisfied, subsection (4) must be complied with no later than 19 October 2019

The Act is quite well drafted and they expected stalling. It even includes a draft form of the letter. It does not specify a remedy, so I'm not sure what happens if it's not complied with, but the deadline for the Benn act is two weeks before the Withdrawal Act.

That provides enough time for the appointment of a new PM by confidence vote...

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    Commentators suggest [citation needed] that if the PM refused to send the letter, opponents would go to court to seek a court order to require him to do so. Failure to comply would result in contempt of court, which can result in a penalty, including incarceration and/or a fine. – Steve Melnikoff Sep 24 '19 at 15:22
  • @SteveMelnikoff: Do you know about the duration of incarceration and amount of fine possible? I imagine most brexiters would consider it the honorable thing for him to (not) do, even if it costs him personally. – user000001 Sep 24 '19 at 15:43
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    @user000001: In the most extreme case: 2 years and/or unlimited fine. – Steve Melnikoff Sep 24 '19 at 15:50
  • @user000001 A custodial sentence of a year or longer would also automatically cost him his seat at Westminster. – origimbo Sep 24 '19 at 16:21
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    @divibisan No, there is no actual rule in the UK that the PM must be an MP. However, due to its political unacceptability, his or her party would probably run an emergency leadership contest to find a replacement. – origimbo Sep 25 '19 at 15:21
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If the PM does not obey the law he could be taken to court over the matter. In that case the court could send the letter on his behalf, requesting the extension.

However, I think Boris will likely send the letter now. He has lost all control and the only way out is a General Election, which he can't get until the letter is sent. Delaying only hurts him and the Tory party more.

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