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Kent were left to rue their decision to insert Gloucestershire on day one of their LV= Insurance County Championship Division 1 clash at Canterbury.
Having reduced the visitors to 46-3 in the first hour, Kent were made to toil for most of the day as Gloucestershire closed on 388-7.
New Zealander Glenn Phillips made 125 with support from Miles Hammond (66) and Oli Price’s career-best unbeaten 48, compiled on his 21st birthday.
Matt Milnes had taken three early wickets to halt a rapid Gloucestershire start as Kent's New Zealand seamer Jacob Duffy proved particularly expensive early on.
George Scott set the tone with a clip off his hips to the rope from Duffy's first ball, and there were already 35 runs on the board from 34 balls when Milnes had Scott trapped leg before for 27.
Milnes looked a constant threat from the Nackington Road End and five deliveries later he had James Bracey (1) caught behind by Sam Billings. Milnes (3-76) claimed his third scalp when trapping Chris Dent lbw for 11.
Gloucestershire recovered to 114-3 at lunch. Hammond, who averaged less than 26 in his 11 County Championship innings this season, brought up his half-century from 90 deliveries while Phillips followed suit from just 71 balls soon after.
Kent got the breakthrough when Grant Stewart removed Hammond to break a stand of 138 with Phillips and make it 184-4.
Phillips reached his century from 124 deliveries, which featured 13 fours and a straight six off South African spinner George Linde. Phillips and skipper Ryan Higgins added a breezy 69 for the fifth wicket to steer their side past 250 before Duffy - switching to the Nackington Road end where he tightened up significantly - claimed his first Kent scalp, getting Higgins (24) to edge to Billings, who had missed the chance to stump him moments earlier.
Price helped the score on to 288-5 before Phillips holed-out to Duffy off the bowling of Stewart (2-74) for 125.
Tom Price mis-timed a pull to Jack Leaning in the deep for 39 to give Duffy (2-91) his second scalp.
Zafar Gohar advanced to 24 not out after sharing an unbroken stand of 38 for the eighth wicket with Oli Price.
Kent's Ollie Robinson said: "I felt like we started the day well. It was a bit of deja vu from our home games this season, we got three early wickets and then weren't able to break that middle partnership.
"They got away from us a little bit but we clawed it back a little bit towards the end. It's a simple one. We need to knock them over early in the morning and try and put a big one on the board and then hopefully bowl them out again. That's the plan.
"The blueprint for the game has been dictated to us. We have to get 500-600 to stand a chance of winning.
"I thought the boys stuck at it well to get the wickets we did.
"It's a big game, we need a positive result and we need to pick up our points but if the pitch doesn't allow us to get a positive result then so be it. We're going to give ourselves the best possible chance."