The Sydney Gazette reported the arrival of the Ruby in Port Jackson from Bengal in September 1811.....
On Saturday evening last 28th September 1811, arrived the ship Ruby, Captain Cripps from Calcutta. She left the Pilot the 28th June and was necessitated to cut out of the Eastern Channel in a heavy gale, with the loss of an anchor; went in to water at Bencoolen the 4th August and sailed again the 8th August 1811 
Three male prisoners arrived in Port Jackson on the Ruby....
William Samuel Windsor Harris Baker. - Born 6 June 1790 at Westminster, London, son of John and Sarah Baker. He was an officer of the East India Company and was tried 13th April 1811 in Bombay and sentenced to transportation for life for sodomy.  He received an absolute pardon in November 1817. It may have been Baker who was on a list of bankrupts published in the Edinburgh Gazette in 1825. He resided at No. 1 Kennington Lane, Newington, Surry and was a silk hat manufacturer. His will was dated 1852 (National Archives).
William Highland. - Tried at Fort William Bengal on 21st December 1810 and sentenced to 7 years transportation for grand larceny. Certificate of Freedom issued 5th June 1818.
John Cullan - Tried at Fort William, Bengal on 21st December 110 and sentenced to 7 years transportation for grand larceny. Certificate of Freedom issued 5th June 1818
Departure for Hobart
The Ruby was chartered by Government to take troops of the 73rd regiment, convicts, provisions and stores to Hobart and Major Andrew Geils (arrived per Providence) of the 73rd regt., who had been appointed Commandant at Hobart was given orders dated 31st January 1812 to hold himself in readiness to sail on the Ruby for Van Diemen's Land. 
On 8th February 1812, Ensigns Greenshields and Holme with the detachment of the 73rd and 80 male convicts were ordered to embark on the Ruby on 10th February 1812 
Thomas Cripps lost command of the Ruby (as explained below) and when the ship departed Sydney in February 1812, Captain Ambrose was at the helm........On Tuesday the Ruby commanded by Captain Ambrose sailed for Calcutta via Hobart whither she conveys the Detachment of the 73rd regiment and 80 male prisoners. Major Geils and family also embarked in the Ruby for Hobart at nine in the morning on which occasion a Lieutenant Colonel's Salute of nine guns was fired from Dawes's Battery - His Excellency the Governor and Mrs. Macquarie accompanied Major Geils and family down the Harbour and returned about midday. 
Departure from Van Diemen's Land
The Ruby sailed from VDL for Bengal on 26th March 1812, suffering the loss of her top mast during severe weather on the voyage. 
Captain Thomas Cripps
Government Public Notice Sydney 12th September 1812
Whereas Thomas Cripps who arrived in this colony in the year 1811, in Command of the ship Ruby, of and from Calcutta, has in a most daring and piratical manner effected his escape on the 10th instant on board the Brig Cyclops, bound for Calcutta, attended with circumstances of a felonious nature, and in direct violation of the Port Regulations and Orders, and to the serious Prejudice of several persons to whom he at this time stands indebted for large sums of money, it becomes necessary that the utmost vigilance should be exerted to prevent the recurrence of such perfidious conduct in future and that such Regulations as may appear best calculated to prevent the evil complained of should be speedily adopted.
His Excellency the Governor therefore orders and directs that the Naval Officer shall board each ship or vessel about the leave the harbor at the Time of her unmooring or weighing anchor in Sydney Cove and remain on board until she shall have got clear of the heads at Port Jackson at which time he is to deliver over the Port Clearance to the Master or Commander of the Vessel and to return having duly enforced the Port Regulations. etc 
 Colonial Secretary's Papers. Copies of letters sent: local and overseas, 1809-1813 Item: 4/3491 Page: 205
 Musters and other papers relating to convict ships. Series CGS 1155, Reels 2417-2428. State Records Authority of New South Wales. Kingswood, New South Wales, Australia
 Ancestry.com. New South Wales, Australia, Convict Registers of Conditional and Absolute Pardons, 1788-1870