Simm was met at and accompanied out of the prison by his wife Heete, calling, "Merry Christmas, everyone!" to journalists waiting at the gate.

On February 25, 2009, Simm was convicted of treason and of transmitting internal intelligence to the Foreign Intelligence Service of the Russian Federation (SVR) and sentenced to 12 years and six months in prison. In a civil suit filed by the Ministry of Defence, the courts also ordered Simm to pay 20,155,000 Estonian kroons (nearly €1,380,000) in damages caused by his crimes.

With a December 5, 2019 ruling, Tartu County Court decided to release Simm early on probation. The court sentenced him to probation through March 18, 2021.

The court ordered him to submit to supervision of conduct, additional verification requirements and obligations as well as additional obligations aimed at reducing the risk of his committing new crimes and disciplining the convicted person.

In Simm's case, the court assessed his risk of recidivism to be very low. The court found that Simm's access to various classified information and documents that could be of interest to foreign states or their organizations is incredibly limited. Likewise considered to be factors reducing his risk of recidivism are his old age and the condition of his health.

Simm served 11 years and two months of his 12 year, six month sentence.

According to the investigation of the Internal Security Service, Simm transmitted thousands of classified documents to the SVR over a period lasting nearly 13 years.

Several Estonian politicians, including Minister of Foreign Affairs Urmas Reinsalu (Isamaa), have called Simm's early release from prison incomprehensible.

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