I think that one particular point in which Benjamin would feel that Hegelian notions of history are inaccurate would be in its embrace of progressive identity. For Benjamin, the vision of history that is earnest to the teachings of Hegel and Marx is one where historical progress towards a directed end is automatically understood. Accordingly, historical progress involves directed evolution of thought and action to an end that is affirming of both the spirit of dialectics and the individual autonomy within it. Benjamin takes issue with these notions. In his "Theses on the Philosophy of History," this is evident. In Thesis XI, Benjamin makes a fairly strong rebuke of the notion of historical dialectics that stresses a particular group of individuals are on the "right" side of history:
The conformism which has dwelt within social democracy from the very beginning rests not merely on its political tactics, but also on its economic conceptions. It is a fundamental cause of the later collapse. There is nothing which has corrupted the German working-class so much as the opinion that they were swimming with the tide. Technical developments counted to them as the course of the stream, which they thought they were swimming in. From this, it was only a step to the illusion that the factory-labor set forth by the path of technological progress represented a political achievement.
Benjamin's critique of the Hegelian notion of historical consciousness is seen in this Thesis. It has helped to feed into a "conformism" that establishes an idea that there is a "swimming with the tide." For Benjamin, this is misinformed historicism. It feeds the illusion that there is a directed end towards historical consciousness and that individuals need to "get right" with this vision of the good.
Illuision is where Benjamin feels that Hegel's notion of history resides. For Benjamin, the Hegelian vision that became coopted by the Marxist social democrats was rooted in this misunderstanding. This was something that he feels is wrong in both its assertion and how it has been understood: "Social democratic theory, and still more the praxis, was determined by a concept of progress which did not hold to reality, but had a dogmatic claim." "Progress" as defined by Hegel "did not hold to reality," but rather in dialectical "dogma." In Benjamin's mind, the historicist claim that Hegel and Marx make in their thinking is flawed because it fails to understand a condition of being in which there is no progress, but actually regression. Benjamin's own historical context had to have played a role in this dark view of human consciousness. Benjamin had to have been impacted by the crumbling condition of political activity in the late 1930s, where alliances between Stalin and Hitler did much to corrupt anyone's notion of "historical progress." In this vein, Benjamin offers a critique of the progress and the sense of positivism that are intrinsic to the Hegelian notion of history.