Winterstale were you able to make your travel connections okay on this trip? Wife and I are planning the same route (SJU to EIS) from Southwest to Intercaribbean, using TSA Precheck with about the same time window (90min.). Have been sweating over this one for months—especially after I heard about a recent spate of Intercaribbean flight cancellations due to pilot shortages. Last time I tried to fly SJU to EIS in 2015 on another island carrier they cancelled the return trip with no explanation. Hoping to avoid a similar scenario this time but didn’t want to do the STT to Tortola ferry thing again. Taking my chances and hoping it pans out.