How can East Africa compete with the rest of the continent?
While East Africa's nations have enjoyed great success in other sporting disciplines, the region's national football teams have largely failed to make a mark on the continent's soccer scene.
Kenya and Ethiopia have a plethora of elite long and middle-distance runners, Rwanda has its cycling sensations., Uganda boasts of a thriving motosports scene, while even South Sudan's roster of basketball stars grows every year.
East Africa is as sports mad and trophy-hungry as the rest of the continent, but international football success eludes the region's sporting fraternity.
Heartbreak, near misses, and underwhelming performances have been the prevailing story for CECAFA's national teams over the years.
According to the coach of Proline FC, of the Uganda Super League, Mujib Kasule, the problems that have hamstrung the Ugandan national side over the last 40 years run deep.
"Qualifying for the World Cup is no mean feat," he told KweséESPN. "You need to have the right players, a deliberate plan, investment, and a bit of luck.
"Uganda has never had that."
It hasn't all been doom and gloom, with evidence in recent years that the region's fortunes are set to improve.
Uganda ended their near 40-decade wait for a spot in the Africa Cup of Nations when they qualified for the 2017 African Cup of Nations, but weren't able to follow that up with World Cup qualification despite a valiant effort in qualifying.
"We need a deliberate and well coordinated ten-year strategic plan," Kasule continued.
"The Federation of Uganda Football Associations must come up with a technical plan, the government and corporate sector [must] invest in it, and the clubs must fully professionalize it in order to produce players that can standout anywhere in the world and also feed into the Uganda Cranes."
The Kenyan national side have periodically produced dazzling football, and have boasted fine players over the years, with the likes of Dennis Oliech, Joe Kadenge, McDonald Mariga and Victor Wanyama all turning out for the Harambee Stars.
However, Kenya have never qualified for the World Cup and haven't made the AFCON since 2004.
Former Harambee Stars coach Francis Kimanzi told KweséESPN that progress must start with progress in regional competitions, and specifically, CECAFA-organised tournaments.
"First of all we must compete regionally," he began. "It is not about selecting players and holding them in the training camp and assuming that just because you have been in the camp, you can get a World Cup slot.
"No. It is a real journey, a journey that requires joint effort."
Unlike West Africa's footballing giants, whose benches are littered with stars plying their trade in European top leagues, most East African nations are far more reliant on players in their respective local leagues.
While the quality of East African football is improving - as evidenced by the region improved representation in the CAF Champions League and Confederation Cup - the leagues still lack the competitiveness and quality of Europe.
Regularly, however, local tournaments and teams must contend with insufficient sponsorship, a lack of regulatory support and poor administration from national governing bodies.
These limitations affect the quality of competition, and consequently keep fans away.
"When we have CECAFA [international tournaments] here, it is not attractive anymore and you can see that teams don't want to bring their senior players to the tournament but they only bring development teams," Kimanzi added.
"If there is that competitiveness and motivating aspect the tournament will be a more valuable event to European-based players."
Despite Rwanda's reputation as one of Africa's top cycling countries, the 'Land of a Thousand Hills' is also yet to replicate their success on the tarmac in the pitch.
They've qualified for AFCON just once, in 2004, and have never even come close to qualifying for soccer's biggest showpiece.
"One of the things that has made it difficult for us to qualify for the AFCON and the World Cup is preparation," former Police FC coach Innocent Seninga told KweséESPN. "We need to prepare the players early and get ready for the qualifiers.
"We need to go back and prepare the players from a young age and bring them up properly and develop a new generation of Rwandan footballers."
Seninga also believes that bolstering the profile of regional tournaments will give East Africa the competitive edge it seeks.
"We have to be organised," he added. "You see West Africa have done it and now it will be difficult to reach them.
"We have to make tournaments like CECAFA regular at club and national level and we have to make sure [there's an] incentive that can attract players."
While East Africa certainly boasts the passion and the fervour to fuel the region's national sides, it appears that progress will be slow unless organisation, financing and long-term strategic planning is put in place.
Could a greater presence of CECAFA-organised competitions among club sides and international teams be the first step in ensuring East Africa can compete with the rest of the continent?