Massa ended up 11th at the end of the session ahead of Fernando Alonso, who may have taken some pleasure from finishing 12th had it not been for a gearbox failure with 30 minutes remaining.
Once again, Red Bull did not appear to lose out on the long straight in sector three where the team had feared the power deficit of its Renault engine would be a burden. A few cars headed back out, but apart from Grosjean complaining about his brakes again, there was nothing much to phone home about.
Ricciardo had just joined him with 1m 44.880s when Perez got it wrong going into Turn 8.
Bottas, who had languished down the order after the run on softs, was the first driver to bolt on a set of super-softs half an hour in, but it was Raikkonen who disrupted Verstappen's dominance with his first proper effort on the compound.
Williams rookie Lance Stroll was an impressive sixth quickest, two weeks after scoring his first points at his home race in Canada. Sergio Perez, Jolyon Palmer and Verstappen all struck the barriers at various stages on Friday.
"We expected difficulties on this track, so we can be happy with the performance of the auto".
The first practice got underway under a clear sky with track temperatures at a blistering 54 degrees C (129 degrees F).More news: Puerto Rico gov upholds statehood in vote hit by boycott
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In the morning, Bottas, who set the maximum speed of 370 km / h in the inaugural race past year, was a little frightened at turn # 10 but managed to avoid contact with the low wall.
Vettel, by contrast, had a solid day.
"When you can do consistent laps without any mistakes, you can get the tyres to work as well".
"Most of the cars had problems today".
"Where do we start?" he said after being asked to explain why he did not consider fifth position a good performance.
To cap another frustrating weekend for the team's Dutch starlet Verstappen, the 19-year-old was forced to retire on lap 11 with major engine troubles forcing him into his fourth retirement in the last six races.