The situation in Backhill Village had essentially solidified after a few days, with Rocky using Sirius City as a shield. Although Howling Sky was in an awkward position, he acquiesced due to his sense of responsibility and relationship with Rocky. Although he didn't actively help, he placed the fleet outside the city as a form of deterrence, effectively thwarting the advances of City of Fury.
However, this exact outcome played right into the hands of Rick and his comrades, as they had anticipated this development!
To target Rocky, not only had they thoroughly investigated him personally, but also everyone related to him was scrutinized, including Howling Sky's reactions. Therefore, everything Howling Sky was doing not only failed to surprise Rick and his group, but in fact, it was exactly what they had hoped to witness.