Hey @rickkas7 and @derthere, I have the SH1107 128x64 variant of the OLED Featherwing and I was able to re-create the issue. Adding the 3V3_AUX configuration in the setup routine solved it.
SystemPowerConfiguration powerConfig = System.getPowerConfiguration();
powerConfig.auxiliaryPowerControlPin(D23).interruptPin(A6);
System.setPowerConfiguration(powerConfig);