From 2007 onwards she focused more on German and French road races. She is a two-time winner of the Hamburg Half Marathon and was the 2012 winner of the BIG 25 Berlin. She has a 10K best of 32:32, a half marathon best of 1:08:36 and a marathon best of 2:30:34.
Chepkwony missed the 2008 season but successfully returned in 2009 with a focus on road events, winning the Course de l'Escalade for a second time and taking the Hamburg Half Marathon title with a time of 1:15:22 for her debut over the distance.[6][9] She competed in smaller scale events in 2010 but was rewarded with numerous victories, including the Lotto Cross Cup Brussels,[10] the Kö-Lauf and Alsterlauf Hamburg10K runs, half marathons in Hamburg and Altötting, and the Zürcher Silvesterlauf. In 2011, she retained her titles in Brussels, Hamburg and Zürich, as well winning the Course du Noël for a second time.[8] In addition, she won the Murtenlauf and Kerzerslauf races for the first time.[11][12]
The 2012 saw Chepkwony begin to participate in higher standard road competitions. She ran a personal best of 68:36 minutes for third place at the Berlin Half Marathon,[13] then won the BIG 25 Berlin race.[14] This earned her a place in the elite selection for the 2012 Berlin Marathon and in her first attempt at the classic distance she managed to finish in 2:30:34 hours, coming in seventh place.[15] Aside from her exploits in Berlin she repeated her win at the Kerzerslauf (setting a course record), won the Grand Prix von Bern 10-miler,[16] and had another win at the Course du Noël.[8]