Harambee Stars suffered another setback in their 2027 Africa Cup of Nations qualifying campaign after falling to a 1-0 defeat against Guinea at Stade 28 Septembre in Conakry on Thursday evening.
Serhou Guirassy scored the only goal of the contest in the first half as the Syli National bounced back from their opening defeat to South Africa and secured their first three points in Group D.
Kenya travelled to Conakry looking for an improved result after being held to a 1-1 draw by Eritrea in Nairobi in their opening qualifier.
Instead, Benni McCarthy's side were left still searching for their first victory of the campaign, while their difficult away record against Guinea continued.
The match marked Kenya's fifth visit to Guinea, with Harambee Stars yet to record a victory on Guinean soil.
McCarthy made four changes to the team that started against Eritrea. Manzur Okwaro moved to left-back, while Mike Kibwage partnered Frank Odhiambo in central defence.
Duke Abuya captained the side and formed part of a midfield containing Crispine Erambo and Ben Stanley Omondi. Mohammed Bajaber was also handed a starting role in attack.
Guinea broke the deadlock shortly after the half-hour mark following a passage of play involving Aliou Balde and Guirassy.
Balde's clever involvement created the opening before Kenya briefly recovered possession through Erambo. The midfielder was unable to fully clear the danger, however, and the ball eventually fell back into Guirassy's path.
The Borussia Dortmund striker made no mistake, firing beyond goalkeeper Byrne Omondi to give the hosts the lead.
Kenya had an opportunity to respond just before half-time when Job Ochieng made his way into the penalty area, but a heavy touch during the move prevented Harambee Stars from producing a clean finish.
The visitors then almost conceded again moments later after losing possession.
A long pass from deep released Abdoul Karim Traore, who forced Byrne Omondi into an important save to keep Kenya within one goal heading into the interval.
McCarthy responded at half-time with a double substitution, introducing Ryan Ogam and Timothy Ouma for Micah Obiero and Job Ochieng as Kenya looked for greater attacking threat.
The changes nearly produced an equaliser around 10 minutes into the second half when Ogam struck powerfully towards goal, only for Guinea goalkeeper Mohamed Camara to make the save.
Kenya made another attacking adjustment around the hour mark as Shariff Musa replaced Bajaber on the left flank.
Harambee Stars increased the pressure as the second half progressed, but Guinea remained organised defensively and successfully protected their narrow advantage until the final whistle.
The victory moved Guinea onto three points after two matches, reviving their qualification hopes following their opening 2-1 defeat to South Africa.
South Africa remained top of Group D with six points after recording a commanding 5-0 victory over Eritrea.
Kenya, meanwhile, have collected one point from their opening two qualifiers and will need an improved return when their AFCON campaign resumes.
Before then, McCarthy's side are scheduled to travel to Rwanda for a friendly against Amavubi on Monday, October 6.