"I was drawn to 'I Wish I Was A Mole In The Ground' at the time in Dublin when traditional music was centred round this pub The Cobblestone, and it was under threat.

[7] Siobhán Long of Irish Times scored this release 4 out of 5 stars, calling this album and stating that "the nocturnal, muzzy soundscape builds on what he conjured on his solo debut" and "Flynn's reach is both wide and deep, embracing this time around two songs from Ewan MacColl's catalogue and layering fresh meaning on both".

[8] In a feature interview for Loud and Quiet, Ollie Rankine describes Flynn as "being one of the genre's most recent offshoots and contending with hordes of different song variations before him, Flynn still succeeds in finding his niche" with his focus on a Dublin-specific sound and stated that this album "offers an abstract fantasy, a fleeting glimpse of what could exist when all that is truly Irish remains".

[9] Neil Spencer of The Observer rated this album 4 out of 5 stars, calling it a "blast from the past" with "songs emerge from walls of growling guitars and doomy drones and disappear into distorted electronica".

[11][12] Editors at Stereogum also chose Look Over the Wall, See the Sky as the Album of the Week, with critic Ryan Leas remarking that the music is "wracked with sadness, but makes it vivid, immersive, and strikingly beautiful".