diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 4ebbbab..bd9e541 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -38,6 +38,14 @@ jobs:
       - name: Check for PDF artifact
         run: file ${{ env.PDF_NAME }} || grep -q ' PDF '
 
+      - name: Delete old release assets
+        if: github.event_name == 'push' && github.ref == 'refs/heads/main'
+        uses: mknejp/delete-release-assets@v1
+        with:
+          token: ${{ secrets.RELEASE_TOKEN }}
+          tag: latest
+          assets: ${{ env.PDF_NAME }}
+
       - name: Release PDF artifact
         if: github.event_name == 'push' && github.ref == 'refs/heads/main'
         uses: softprops/action-gh-release@v2