To navigate the increasing sustainability pressures from regulatory bodies and various stakeholders, this research explores organizations’ strategic responses and communication strategies within the transport logistics sector, particularly focusing on Deutsche Post DHL Group. Grounded in institutional theory, this paper examines how these organizations adapt their strategies to be perceived as legitimate while balancing economic objectives with environmental obligations. The study employs a qualitative longitudinal analysis combined with a thematic analysis of secondary data from various reports, websites, and social media to comprehensively understand the evolution of strategic responses and communication practices within the transport logistics industry.  The findings reveal that DHL Group has progressively enhanced its transparency and specificity in sustainability reporting, driven by stricter regulations and rising stakeholder expectations. The organizations’ strategic responses, including strategies such as acquiescence, compromise, manipulation, justification, and decoupling, have evolved from initial resistance and superficial compliance to a more integrated and proactive approach, highlighting the balance between financial stability and sustainability initiatives. Furthermore, the research underscores the crucial role of strategic communication in influencing stakeholder perceptions and managing expectations to secure organizational legitimacy.