During the putting down of the Pazhassi Rajah's uprising and the associated outbreaks of resistance by the Moplahs to the presence of the East India Company in the Malabar, large numbers of Indian's were thrown into gaols in Calicut, Tellicherry and Canannore.
These gaols were run both directly by the East India Company and also by private gaolers would contracted with the EIC to run prisons.
The gaols were almost certainly highly over crowded and insanitary. The prisoners inside the gaols were actively in planning their escape and attempting to make prison break outs.
The following two accounts from Calicut in 1802 and 1808 describe events during these breakouts. It is not entirely clear exactly when these events took place.
Communications were often slow in those days. The first breakout probably took place in the months immediately before March 1803. The second event probably took place a year to 18 months before the news of the event appeared in the British papers.
The first breakout was yet another worry for the future Duke of Wellington as he was planning the concentration of his forces in the South of India for the campaign he was to fight later that year with the Mahrattas, and which would be capped with his victory at Assaye on the 23rd of September 1803.
'Camp at Tuddus, 17th March, 1803
'I have received a letter from Colonel Montresor, from Calicut,of the 6th, from which I learn that the rebellion has spread much in Malabar, and that the rebels were in force not far from that place. The criminals confined in the gaol at Calicut had also got loose; sixty had made their escape, many were killed and some wounded in attempting it. The guard over the gaol had been surprised. Those people were chiefly rebels confirmed by Colonel Stevenson. 'I mislaid Colonel Montresor's letter yesterday evening, otherwise I should send it to you, but I have above stated the outlines of the information which it gives. I now enclose a letter which I have written to Colonel Montresor upon this subject, and if you should approve the directions it contains, I beg you will allow it to be forwarded to him. In fact, no more can be done in this season than I have there stated. It will be useless to leave more posts, or to have more men in Wynaad than the post at Manuntwaddy and those on the tops of the ghauts. If there were two battalions in that district they would be obliged to remain shut up in their posts, where they would be useless; at the same time, the greater the number of troops to be left in Wynaad, the greater will be the difficulty of providing for them. 'I received yesterday your letter of the 15th instant. I have sent Govind Rao with a message to Bappojee Scindiah of the same kind with that which I formerly sent, of which you approved. 'I shall march to-morrow to Misserycotta, where I shall halt next day to allow Major Malcolm to join me, and to give time to Govind Rao to arrange every thing with Bappojee Scindiah'
Lieut. General Arthur Wellesley. 
The second report is taken from the Morning Chronicle, one of Britain's leading papers at the time published in London, and reports a desperate act of resistance on the part of a band of Moplah's or Mappilas who knew that they otherwise had no hope of surviving beyond the following morning, when they were going to be executed by the EIC authorities.
They went down fighting, successfully killing and wounding several of the EIC forces.
"The following very extraordinary circumstance lately took place at Calicut: -Seven desperate Mallays who had been the terror of the adjacent country, having carried away the cattle, set fire to the cottages, and murdered several of the natives who opposed their depredations, were apprehended and lodged in the public gaol, when, during the period of their confinement, they behaved in the most refractory and resolute manner. On being brought to trial, several charges were brought home to them,. and they-all received sentence of death; but the evening previous to their execution, they rose on their guards, whom they murdered ; and possessing themselves of their muskets, 'bade defiance to the keeper of the prison and his assistants. The Officer commanding in the district, with a small detachment of seapoys, attempted to scale the walls of the prison; the doors and windows being blockaded. within; but he was repulsed with the lost of several men ; the assailants however being reinforced from an adjacent station, and the desperadoes finding themselves overpowered, set fire to that part of the prison in which they were confined, and refusing all assistance, perished in the flames. Fortunately the rest of the prisoners were rescued, and a part of the building was saved from destruction. 
The dispatches of ... the duke of Wellington, compiled by Lieut. colonel John Gurwood, 1837... page 422.
 Morning Chronicle. Monday 08 August 1808. From the British Newspaper Archive Site.
Prison photo courtesy of Epoch Times.