According to residents of Butenga Estate in Kira, where Kalyegira lives, he has not been seen since Friday last week - the same day a colleague said he last spoke to him. His mobile phones have remained switched off, prompting concern among family members and fellow journalists.
While Kalyegira had the knack of a nosy dog typical of a journalist, he lived a rather quiet life, almost like a recluse, with even those close to him never knowing much about his family.
But on Sunday, a message circulated on Butenga Estate's WhatsApp group alerting residents to his disappearance.
"His phones are switched off," the message stated, adding that Kalyegira's immediate family had been informed.
"We remain hopeful for his safe return," it added.
Journalist Charles Mwanguhya, a longtime colleague and friend, said he last spoke to Kalyegira on Friday, which was also his birthday.
Several journalists at Daily Monitor, whose parent company Nation Media Group Uganda has itself come under pressure following the closure of its media outlets by security operatives over the weekend, also said they had been unable to reach him.
Police spokesperson Rusoke Kituuma had not responded to media inquiries by the time of publication regarding Kalyegira's reported disappearance or whether he could be in the custody of any security agency.
Kalyegira, a columnist with the Daily Monitor and a digital data researcher, is widely known for his independent political analysis and criticism of government policies.
His last known post on X was published five days ago but before then, on June 18, he commented on an online exchange between Chief of Defence Forces Gen Muhoozi Kainerugaba and opposition leader Robert Kyagulanyi, popularly known as Bobi Wine.
Sharing a screenshot of the exchange, he wrote: "Bobi Wine and MK exchanged jabs. Finally, MK snapped."
"For the first time, MK took on Bobi Wine on a level playing field, without SFC troops to arrest Bobi Wine. Lacking debating skills and unable to arrest BW, he threw in the towel in frustration. Bobi Wine 4, MK 0."
His reported disappearance comes at a tense moment for Uganda's media landscape, following the closure of Nation Media Group Uganda's television, radio and newspaper operations by security personnel over the weekend.
It also follows reports of the detention of former Ethics and Integrity Minister Miria Matembe, now a government critic.
Police spokesperson ACP Kituuma Rusoke had not responded to media inquiries by press time regarding reports that Kalyegira is missing or whether he could be in security custody.
Kalyegira has, over nearly three decades, established a reputation as one of Uganda's most widely read political commentators and researchers.
His criticism of government has earned him the wrath of the state in the past. He has been accused of sedition and criminal libel and detained in Luzira Prison in the past.
Many on social media who follow Kalyegira are hoping he has travelled upcountry on one of his regular photography and documentary activities and is maybe out of network range.
But his current silence is eerily unusual.