Trying to Fit the Ocean in a Cup has received mostly favorable reviews from the critics to judge the album.

Of the positive reviews, The Phantom Tollbooth gave the highest rating of a four and a half stars out of five, and the four star ratings came from Allmusic, Christianity Today and Jesus Freak Hideout, which it got one eight-star review from Indie Vision Music.

The Phantom Tollbooth's Shawn Dickinson proclaimed it as, "a memorable disc which showcases Josh's witty songwriting and capacity for highly infectious hooks," and noted "how the entire project fits together and is an enjoyable experience from beginning to end.

"[3] Jesus Freak Hideout's Adam Dawson called the release "enjoyable, catchy, and full of relevant Christian themes", which it "may not perfect, occasionally suffering from a bit of overproduction and lack of acoustics", yet vowed that it was a "promising debut.

"[5] Cross Rhythms' Niall Dunne said that "as with any good album, 'Trying To Fit The Ocean In A Cup' goes much deeper than the surface level radio hits that inevitably do well.