It's a question that fans of the franchise pondered for 17 straight seasons, before head coach Sean McDermott and an upstart bunch of players were able to vanquish the hated playoff question in 2017. But even McDermott would tell you that the success that Bills team enjoyed that season was not sustainable.
A debilitating cap situation that had to be corrected combined with a quarterback position that was in need of an upgrade left the Bills in a transition year type situation in 2018 despite the best efforts of the players and coaches.
Now with their salary cap issues in the rearview mirror and the roster overhauled, Buffalo could be in position to make another run at the postseason.
Here are four factors that could facilitate a return to the playoffs.
1. Top 5 defense
Buffalo finished second in the league in total defense last season. With 10 of 11 starters returning and a host of additions in free agency and the draft, one could argue that the unit is even deeper than it was last season.
With that kind of continuity, league history has shown that such defensive units can stay in the top five for two or three seasons straight.
Last season, only two of the five top defenses reached the postseason (Baltimore, Chicago). The main reason the others did not was because their offenses finished 20th, 27th and 30th.
Though there is no guarantee that a top five finish on defense will get you to the postseason, it is certainly an asset that can help get you there if there's a balance of productivity on the other side of the ball.
2. Revamped offensive line
The Bills inability to win consistently at the line of scrimmage on offense played a major role in Buffalo's struggles last season. It compromised their run game, their pass protection and their ability to stay on the field and finish drives.
Now equipped with an arsenal of options for all three interior positions and right tackle, Buffalo should be able to craft a front five capable of winning battles on the line each week.
That should translate into a more balanced offense, more time for Josh Allen to make plays from the pocket in the passing game and more drives finishing in the end zone rather than with a punt.
By no means are there any guarantees that Buffalo's new offensive line will come together and be demonstrably better than last year's unit, but with new line coach Bobby Johnson pulling the strings the odds are very good that happens.
Click through to see the best black and white photos from the team's offseason practices.
3. More weapons
A bulk of the offseason work focused on the offensive side of the ball and understandably so. One of the bigger considerations was adding skill position weapons to diversify the team's attack and present opposing defenses with more difficult decisions when it came to their play calling and matchups.
The additions of Cole Beasley, John Brown, Frank Gore, Tyler Kroft and Andre Roberts should all aid in that effort.
No longer can defenses simply focus all their attention on LeSean McCoy or Josh Allen. In the passing game, rolling coverage to Robert Foster's side of the field is no longer an easy choice to make because Brown can stretch the field just as well on the other side of the formation.
Can you afford to sit in cover two with two safeties deep if Beasley and Zay Jones are picking up eight to 12-yard gains underneath every single pass play?
And those are just some of the veteran options at Brian Daboll's disposal. If rookies like Dawson Knox and Devin Singletary contribute sooner rather than later this season, there will be even more matchup issues for opposing defenses to address.
4. Schedule of opponents
While it's hard to predict just how tough a schedule the Bills will face in 2019 based on the 2018 record of their opponents, it does provide some insight into what Buffalo will be up against this fall.
On the surface the prospects are certainly encouraging when it comes to Buffalo's 2019 opponents, as they'll face only four playoff teams from the previous season (Baltimore, Dallas, New England, Philadelphia).
In fact, the Bills will have more games against teams with sub-.500 records (7) in 2019 than playoff teams (5).
Buffalo also has seven games against teams with new head coaches, including three in the first seven weeks of the season. League history has shown us that most new coaches struggle to get off to fast starts, much less have successful years in their first season on the job.
The Bills top flight defense will also square off against opponents in five games who will have a new quarterback at the helm this season. No matter how prepared any of these new signal callers might be it pales in comparison to the experience of Buffalo's defense, now largely in their third season together.
There is an additional advantage in Buffalo's 2019 schedule that goes beyond the opponents. From Week 3 to Week 9, the Bills have five home games and a bye. If they can stack some victories during this front half of the schedule, they could position themselves very well for the stretch run.
Obviously, there are other factors besides those listed that could come into play and impact the Bills playoff aspirations.
To what degree can Buffalo's special teams improve under new coordinator Heath Farwell? Can the team stay as injury free as they did last season? And can that ingrained team culture that appears so strong carry them through a rough patch or two during the season?
Entering year three under McDermott, the Bills are certainly reaching a stage where they should experience success, and believe they're more than capable, but making it happen in a league this competitive and with so many other variables is no easy task.
They will have to earn every win they can get, but there is a strong likelihood that Buffalo can contend for their second postseason berth in three years.