Eddie's postings are not quite spot on.
He is completely correct about the “absolute” nature of the offence of No Insurance and you will be very hard pushed to achieve an acquittal should you or your boyfriend decide to plead not guilty. The circumstances you describe amount to mitigation only.
However, there are a couple of points that Eddie has made which are incorrect:
The “New Drivers” regulations state that a driver who attains 6 or more points within 2 years (not six months) of passing his first driving test reverts to provisional status. The court has no discretion over this as it is actioned by the DVLA. An ordinary test (not and extended test) is then required (both parts) to regain a full licence.
Finally there is no possibility of being sent to prison for the offence of No Insurance, regardless of how many times it is committed. The maximum penalty is a fine of £5,000 and an unlimited period of disqualification. The likely penalty for a first time offender is six points (the minimum available for the offence), a fine of about one and a half week’s net income (reduced by a third for an early guilty plea) plus a £15 Victim Surcharge and about £60 prosecution costs.