This thesis seeks to offer a systematic theological reflection upon the nature of preaching as both dialectical and heraldic, through a specifically Scriptural and pneumatological lens. The thesis begins, in chapter I, by mapping preaching's inseparable connection to Scriptural content, outlining the fundamental importance of the overarching 'clarity' and 'unity' of Scripture as vital entry-points to interpreting Scriptural tension. Scriptural 'unity' will be mapped with a variety of modern biblical and theological approaches to canonicity, and Scriptural 'clarity' will be mapped via the thought of the key Reformers, Luther, Zwingli, and Calvin. Having outlined these important foundational parameters for approaching Scriptural dialectics, it will be argued – leaning upon Barth's construal of biblical tension – that the concept of theological dialectic must be embraced within a theology of preaching, but without allowing it to override the preaching task. Upon this basis, it is then explored, in chapter II, what kinds of biblical tension may exist, since various terminology for 'dialectic' and 'paradox' within the theological and philosophical tradition have rendered their meanings increasingly obscure. Drawing upon a wide range of different thinkers for both clarification and construction – including Eckhart, Hegel, Kierkegaard, Chesterton, Barth, Tillich, Milbank and Žižek – it is argued that four primary dialectical modes exist within theological discourse, connoting 'incompatible' polarities, 'harmonised' polarities, 'hierarchical' polarities, and 'antagonistic' polarities. Having articulated a more specified account of dialectics, then, these dialectical modes are applied, in chapter III, to a theology of 'heraldic' proclamation. The notion of the heraldic motif for preaching will be explicated alongside its twentieth-century homil Following this, a more complex, dialectically-aware conception of heraldic preaching is offered. It will be argued – again, using Barth – that a theology of homiletical 'confidence' alongside dialectics is possible within this revised understanding of the preaching task. It will also be established that part of the heraldic role of preaching is to engage dialectically in different ways. This will be highlighted – with specific applications to various dialectical sermonic possibilities – by re-conceiving preaching as an act of contingent dialectical correctivity. This special license for preaching to articulate truths 'dogmatically' in the midst of dialectics is then buttressed pneumatologically, in chapter IV, where the notion of preaching as both Scripturally expository and pneumatologically prophetic will be established and conjoined. This will include an account of prophetic illumination and prophetic discernment in preacher and congregation, as well as a distinct focus upon the nature of preaching as pneumatological 'encounter', 'manifestation', and 'moment'. It will be seen that understanding preaching as 'pneumatological moment' offers a theological key to interpreting the relationship of dialectics to preacherly decisiveness. This will serve to present a robust account of the paradoxically heraldic and dialectical dimensions of Christian proclamation.