Is the second shell in the mag on the carrier, or still in the mag when the bolt locks back?
Also, are you shooting a standard, field grade 11-87? If you are, and if you are using target grade shotshells, there may not be enough port pressure to completely cycle the action.
When the 11-87 was introduced, it was intended to cycle 3" and 2-3/4" FIELD loads - - NOT 2-3/4"
target loads.
Special target guns for the 11-87 Premier Trap and Premier Skeet were offered with NON PRESSURE
COMPENSATED barrels for target loads. In essence, those models came with barrels that were 2-3/4" chamber only and had the older, 1100 2-3/4" chamber gas ports.
This is why Remington went BACK to the old 2-3/4" chambered, older 1100 style gas ports for their target guns after a ten year run of making 12 ga. 11-87s
I'd bet it's the ammo used with that particular barrel? Try firing some heavy field loads (on a range where it's permitted) and see if the gun cycles. If it does - and the malfunctions were experienced with light target loads, then you have your answer. Read the barrel: if it says "FOR 2-3/4" OR 3" SHELLS" then, you have one of the field grade barrels meant for 12 ga. 2-3/4" 3-1/4 dram equvialent MINIMUM. These barrels will often not cycle 2-3/4 dram eq. adn 3-dr. eq. target loads used for trap and skeet.