Hey!
So, I received this answer from Meris:
"The Model: Cycles is capable of sending MIDI out in the type A or type B spec. Pedal companies like us, Empress, Chase Bliss and others do MIDI over TRS differently than Type A or Type B. Type A and B are different and were defined after the pedal companies had started our way of doing MIDI over TRS. Ottobit Jr and any pedal from these companies requires a MIDI to TRS conversion box with opto-isolator electronics built into it for a MIDI Standard reliable connection. Each of the companies I mentioned have a compatible MIDI to TRS conversion box available, ours is the MIDI I/O and features MIDI in and out, while the others are compatible with our pedals but only have MIDI In and Thru. "
Hope it helps whoever has this issue in the future.
Thanks again!