[13] In that same year the sentinel gained seven sister newspapers as Tribune Co. announces its merger with Times Mirror, adding the Los Angeles Times, Newsday, the Baltimore Sun, the Hartford Courant and three others to the Tribune Publishing operation.

[16][17] In 2018, the Orlando Sentinel and its corporate siblings began blocking access to Internet users in the European Union because their websites lacked compliance with the EU's General Data Protection Regulation act.

[22] However, while many of Central Florida's surrounding communities remained ostensibly conservative, demographic and political shifts in the late 1990s/early 2000 in the central Orlando urban core and inn its immediately adjacent areas became increasingly liberal and/or progressive majority in their makeup.

Following that trend, the paper has endorsed Democratic candidates for president in four of the last five presidential elections: John Kerry in 2004, Barack Obama in 2008,[23] Hillary Clinton in 2016,[24] and Joe Biden in 2020.

[25] In June 2019, the day of President Donald Trump's re-election campaign launch rally in Orlando, the Sentinel made national news when the editorial board published a piece saying it would not endorse the president, among their reasons, "the chaos, the division, the schoolyard insults, the self-aggrandizement, the corruption, and especially the lies.