During the winter of 1906, Door County's largest newspaper, the Door County Advocate, reported that negotiations were underway for the Oak Leaf's purchase by the Sturgeon Bay Stone Company. From the opening of navigation in spring 1906, the Advocate regularly reported the movements and activities of the barge and her escort, the steam barge I.N. Foster. At times the Oak Leaf was paired with the barge Ida Corning on its transport route, but the tow seldom if ever consisted of more than two barges in line. Tugs and barges from other quarries often escorted the Oak Leaf, demonstrating that the various quarries cooperated when their loads of stone had to be delivered to the same destination. During the early years of operation, the Sturgeon Bay Stone Company periodically contracted tugs from local quarries to do its towing.   

Barges and their escorts appear to have spent an inordinate amount of time dodging storms and inclement weather, a reflection of their poor seafaring qualities. On one occasion the Foster and Oak Leaf survived a three week odyssey, dodging storms, seeking harbors and island lees, and crisscrossing the same bodies of water more than once, all in an attempt to get a simple cargo to Petoskey, Mich., a day's sail away in good weather. On another occasion the Oak Leaf rolled so badly on a return trip from Ludington, Mich., that she unshipped her mast and her deck-boiler went over the rail. Indeed, most barges lost on the lakes were victims of shifting cargo that resulted in capsizing.   

Occasionally, however, fatalities occurred even when a barge was not in distress. The body of 30-year-old Francis C. Brown, deckhand on the Oak Leaf, was recovered in Sturgeon Bay on 27 August 1908, after apparently falling overboard during the barge's outbound journey to the Michigan shore. With only two or three men on board, it was unlikely that anybody would witness a sailor falling overboard. Moreover, should an accident be seen, it would take a great deal of time to signal the tug and more time still to turn around the consort--by which time it would be virtually impossible to spot a small head bobbing in a sea of waves.