Town could have been 3-1 up at the turn, but ended up losing by that score after a shocking slump during the second 45.
Both sides needed to win for different reasons, but unfortunately it was relegation-threatened Hartlepool who looked the hungrier.
And Town will have to find a big improvement if they are to rekindle their challenge for automatic promotion by beating Rotherham, another side fighting for League I survival, at the Galpharm a week today.
At least their showing between the 10th minute, when the home side went ahead through Adam Boyd, and half-time gives boss Peter Jackson something to work on.
During that period, the visitors looked like a team with genuine promotion aspirations, and while David Graham grabbed one goal, his sixth in eight Town appearances, he could have had up to half a dozen.
Having shot wide from a Danny Schofield corner before Boyd fired Pool in front from a low Ritchie Humphreys cross, Graham will have been disappointed at scuffing a 17th-minute effort straight at Greek goalkeeper Dimitrios Konstantopoulos after lovely interplay between Andy Booth and the lively Chris Brandon.
That poor finish was forgiven when the Scotsman drew Town level with a 22nd-minute beauty after good play by Brandon and Mark Hudson.
Receiving the ball with his back to goal, Graham's trickery bemused two home defenders, and the on-loan Sheffield Wednesday man finished with a left-foot curler into the keeper's right-hand corner.
Town had a let-off when Boyd's shot hit Phil Senior's left-hand upright and bounced back into play on 27 minutes.
But Peter Jackson's men still had the upper hand, and Booth's 30th-minute header skimmed the top of the bar before Konstantopoulos saved well from Graham's well-struck free-kick two minutes later.
When Ben Clark sold his keeper short with a back header after 36 minutes, Graham looked odds-on to score, but his shot was smothered.
Then, on 39 minutes, the Town man was unable to get enough power into a header from a cross by Brandon, who around the same time, had one shot held, then drove another just wide.
But Town were unable to pick up where they had left off after the break, when Hartlepool took a firm hold.
Senior made fine saves in quick succession from Boyd and Michael Nelson during a 51st-minute home attack which also featured a goalline clearance by Nathan Clarke from Humphreys.
But he couldn't prevent Michael Maidens netting with a swerving long-ranger two minutes later.
The home side were scenting blood, and the busy Humphreys brought another fine save from Senior with a stinging shot.
Town had a 63rd-minute penalty appeal, when Graham tumbled in a clash with the keeper, refused.
Then they had a huge let-off when substitute Matty Robson somehow missed an open goal after being set up by Boyd.
Graham drove a shot just wide during a rare Town attack on 80 minutes, but any hopes of a comeback among the 936 away fans in a 5,468 crowd were dashed after 82 minutes.
This time Aussie striker Joel Porter, making his first appearance of the season from the bench after a knee injury, was the home hero, sweeping home after Boyd stepped over a Chris Llewellyn cross.
Now Hartlepool were flying, and Senior had to make two more saves, first from Humphreys, then substitute David Foley, to prevent even more misery for Jackson.
* Elsewhere in League I last night, Southend stretched their lead to nine points with a 3-0 win over Scunthorpe at Roots Hall.
The goals came from Freddy Eastwood, with his 18th of the season, Lee Bradbury, with his first since moving from Oxford, and Shaun Goater.
Bristol City won 1-0 at MK Don through Steve Brooker.
Next page: Man of the Match >>>
Man of the Match: Phil Senior
Might have been beaten three times, but this defeat could have been even worse had it not been for the work of the homegrown goalkeeper.
How they rated:
Phil Senior Unable to mark his 50th League appearance with a clean sheet, but did produce some fine saves all the same. Rating: 7/10
David Mirfin Continues to keep Andy Holdsworth out of his recognised position, but this wasn't one of his better performances. Rating: 5/10
Danny Adams Back in place of Dan Smith after a five-match absence, but looked like he needed to shake off some rust. Rating: 5/10
Martin McIntosh Not as commanding as he can be, and like teammate Nathan Clarke, never got to grips with Adam Boyd. Rating: 5/10
Nathan Clarke Fell below his normal high standards as the goals concession tally reached seven in three games. Rating: 5/10
Chris Brandon After a couple of average displays, he was Town's liveliest performer, particularly in the first half. Rating: 6/10
Jon Worthington Unable to inspire a victory after winning the League I Player of the Month award for February. Rating: 5/10
Mark Hudson Back from a knee injury for his first start in eight games. Worked hard but still needs to get up to speed. Rating: 5/10
Danny Schofield Unable to inspire a victory after agreeing a new two-year contract and making his first start in seven games. Rating: 5/10
David Graham Scored a cracking sixth goal in eight games, but will have been disappointed by the ones that got away. Rating: 6/10
Andy Booth No shortage of effort and commitment, and helped in defence, but struggled to make his presence felt up front. Rating: 5/10
Turning Point:
David Graham's failure to put the ball past keeper Konstantopoulos in the 36th minute. He had previously scored a more difficult chance, and at that stage of the game, Hartlepool were looking more than a little shaky.
Town taking the lead would have tested them.
Spotlight on the ref:
Cheshire whistler Mike Jones upset Town players and fans alike by turning down a 63rd-minute penalty appeal, but overall, did a decent job of keeping the game flowing. Booked Town's Schofield and Pool's Llewellyn.
Hartlepool United: Konstantopoulos, Williams (D), Nelson, Clark, Humphreys, Turnbull, Maidens (Robson, 69mins), Bullock, Llewellyn, Boyd (Foley, 87mins), Williams (E) (Porter, 74mins). Subs not used: Tinkler, Provett.
