Pompey were presented with a thankless task at Wetherby Road, a match they truly couldn’t win.
Yet challenged to accomplish the feat on a 3G surface alien to Football League players somewhat levelled the playing field.
It was always going to be Harrogate Town’s night, certainly they emerged with considerably more credit than the side which won the FA Cup tie.
The tag of gallant losers would do Simon Weaver’s team a disservice, they were more than worthy adversaries, reducing their League One opponents to a role of scruffy route-one merchants.
Not that Pompey should receive too much criticism for their adopted playing style in pursuit of victory, the necessity to overcome the artificial surface dictated win at all costs.
Jackett’s troops were uncomfortable throughout, painfully struggling to come to terms with the 3G pitch for periods, reduced to quickly pumping the ball forwards. Tough to handle – and also tough to watch.
They even found themselves behind after seven minutes through the ever-dangerous Mark Beck, prompting thoughts of an upset.
Suddenly there would have been those of Pompey persuasion longing for the lights to have remained off during several pre-match power cuts which threatened the game’s participation.
As it was, the first-round fixture kicked off 55 minutes late, although the fitful preparation influenced injuries for Tom Naylor and Sean Raggett before 31 minutes were up.
Still, two stunning first-half goals decided the encounter 2-1 in Pompey’s favour, both arriving in the first-half, and completely out of context with the gritty display.
Then Ronan Curtis, four minutes before half time, crashed in a stunning 30-yarder to maintain his recent improved form.
That was enough to settle a tie played in front of 3,408 and now hands the Blues a second-round home clash with Altrincham, more non-league opposition.
Among three changes to the side which beat Southend, Craig MacGillivray was declared fit to return to his former club – in the town which once served as his home.
Recovering from a quad problem, he replaced Alex Bass in goal, before he heads off for a third stint of Scotland duty.
With Ross McCrorie sidelined through a hamstring injury, the right-back slot went to Brandon Haunstrup following his impressive cameo against Southend which produced two assists.
It marked the Waterlooville youngster’s 50th Pompey outing, albeit in an unfamiliar role considering his left-footed tendencies.
That team selection represented a massive slight on both James Bolton and Anton Walkes, who have both served periods at right-back this season and were named on the bench.
The third alteration was a recall for Gareth Evans at number 10 role, with John Marquis pushed up into his natural central striking role.
Evans returned to the team with Ellis Harrison missing from the squad and remaining on the south coast.
Following the pre-match drama centring on floodlight failure, the match finally got underway at 8.40pm – and within seven minutes the hosts had taken the lead.
Christian Burgess was fortunate to escape a booking when he pulled Beck down on the halfway line after miscuing a clearance.
From George Smith’s resulting free-kick aimed towards the far post, the ball was eventually headed back across goal by Jack Muldoon and there was Beck to nod it home to make it 1-0.
It was wretched defending from the Blues - and now they had succumbed to an early goal.
Pompey levelled on 17 minutes through a wonderful maiden goal for Haunstrup.
He initially exchanged passes with Close to venture up the pitch, before receiving a pass from Ryan Williams, cutting inside and curling a delightful left-footed shot into the far corner.
A first goal on his 50th outing had swiftly drawn Jackett’s men level, one for the youngster to treasure in so many ways.
Harrogate sniffed regaining the lead moments later when Josh Falkingham ran onto a pass to unleash a ferocious right-footed effort from 25 yards.
However, it struck his own team-mate in Beck, much to the Blues’ good fortune, with the attempt firmly on target.
Pompey were forced into a substitution on 24 minutes, when Tom Naylor forced off with injury and Walkes replacing him in a holding-midfield role, the captaincy passed onto Lee Brown.
Harrogate continued to look capable of scoring and, when Beck flicked on the ball once more, Burgess missed his clearance and Muldoon crashed a shot from the left narrowly wide.
At the other end, on 30 minutes, Close’s drive from outside the box was pushed out low down by keeper James Belshaw.
Pompey had to make another substitution through injury on 31 minutes, with Sean Raggett coming off for Paul Downing. In the same minute, Jack Emmett replaced Warren Burrell for Town.
Jackett’s side took the lead on 41 minutes through another excellent finish, this time from Curtis.
The bright Williams laid the ball inside to the Irishman, who crashed an unstoppable 30-yard right-footed shot which comprehensively beat the keeper.
Despite an indifferent first half, the Blues headed in at the interval with a 2-1 lead and in pole position to reach the next round.
The second half began with little of the excitement of the opening 45 minutes as both sides struggled for fluency.
On the hour mark, Evans did flight a ball in from the left which Marquis attempted to bundle past Belshaw at the far post, but twice the keeper thwarted him.
Substitute Thomson, on for Jack Diamond, then fired a shot just past the wide with MacGillivray rooted in a glorious chance for the hosts - and didn’t they know it.
Then Thomson’s corner from the right was met with a towering Beck header, yet he headed it straight into the arms of MacGillivray.
Pompey’s lead was narrow and Brown lashed a left-footed shot agonisingly across the face of goal with 10 minutes to spare.
Yet it remained enough to see out a victory highly effective in its execution, yet not sufficient to eclipse the hardy hosts.