Will the upcoming tournament herald yet another early exit, coupled with a summer of disappointment?
Gareth Southgate is keen to ensure England's past doesn't repeat itself by dropping a majority of the squad's 'old guard' in favour of a new generation of talent. Names such as Jack Wilshere, Joe Hart and Chris Smalling were left out in favour of Jordan Pickford, Ruben Loftus-Cheek and Harry Maguire.
It's an encouraging sign that Southgate's squad represents his philosophy of form over reputation, but it does run the risk of a fairly inexperienced and untested squad finding themselves out of their depth in Russia.
Route to the finals
England found themselves with a fairly straightforward qualifying group against Slovakia, Slovenia, Lithuania, Malta and the Auld Enemy, Scotland.
As expected, the Three Lions qualified with ease, finishing eight points above next best Slovakia and remaining unbeaten across the campaign.
They conceded the least amount of goals (3) of any nation in the European qualifying groups, but they, too, had struggles in front of goal, scoring the second-lowest number of goals (18) of any nation to top their group. Only Iceland (16) scored fewer and topped their group.
Moreover, the Three Lions weren't without problematic results. For instance, they drew to Slovenia away and only beat them 1-0 at Wembley, courtesy of a 94th minute Harry Kane winner. Despite finishing top comfortably, their qualifying campaign wasn't particularly inspiring.
Southgate opted for a somewhat experimental squad, with key omissions including Joe Hart and Jack Wilshere.
The issue with Wilshere's exclusion is that the midfield, therefore, lacks a creative element. If Southgate deploys a 5-3-2 formation, the focus will centre on who starts in midfield. The more cautious option is Dele Alli playing just ahead of Eric Dier and Jordan Henderson, though dropping one of Henderson or Dier for Jesse Lingard is more adventurous.
Furthermore, there are question marks over who is best suited to partner Harry Kane up front - Marcus Rashford or Raheem Sterling - and who starts in the back five as centre-back.
On that note, if Kyle Walker is picked as the right centre-back, this, too, raises debate over the starting right back; Kieran Trippier or Trent Alexander-Arnold.
Whilst the obvious choice is Harry Kane, a lot of expectation will fall on the young Raheem Sterling, who captured his first Premier League title with Manchester City last season.
Tottenham striker Kane scored 30 goals in the Premier League, second only to Liverpool's Egyptian forward Mo Salah, but Kane was poor at the 2016 European Championships and hasn't looked at his best since returning from injury in April, clearly lacking both form and fitness.
This is why Sterling will be England's key player. The forward flourished under Mikel Arteta and Pep Guardiola's guidance, having his best-ever season and contributing to 29 goals overall (scored 18, assisted 11).
Southgate will look to the City winger to help ease the goal-scoring burden on Kane and compensate for the lack of midfield creativity.
Partnering Kane up front will require Sterling to not only act as a second striker to run on to knockdowns and get in behind the defence, but also drop deep to receive the ball in between the lines.
Drawn against Belgium, Tunisia and Panama, the Three Lions should qualify for the first knockout round without struggling.
Such is often the case for England, however, they could well find themselves tested by the unknown quantities of Tunisia and Panama.
Their biggest test, though, will be the might of Belgium, a dark horse for the tournament itself. The Red Devils are a nation studded with star quality, which could prove too much for England to handle.
Phil Jones' performance dealing with Eden Hazard, Belgium's key player, in the FA Cup final could yet be a sign of what's to ensue at Russia. The England centre back failed to contain Hazard's threat and ended up giving away a game-winning penalty in the first half.
A deep run in the tournament is, perhaps, too much to expect for England's young squad this summer. Likely to finish second in Group G, the Three Lions' opponent could be one of Poland, Senegal, Colombia or Japan, all teams that would test the strength of Southgate's squad.
If England were to progress to the quarter-finals, they'll face either the winner of Group F or the runner-up of Group E, likely to be Germany.
This will be where the dream ends, barring a miracle.