diff --git a/.github/workflows/ci-pipeline.yml b/.github/workflows/ci-pipeline.yml
index 94ae54e034..ac588c2d80 100644
--- a/.github/workflows/ci-pipeline.yml
+++ b/.github/workflows/ci-pipeline.yml
@@ -1892,19 +1892,19 @@ jobs:
           path: release_notes_bins
 
       - name: Update CI Check Run (Cancelled)
-        if: needs.pages-build.result == 'cancelled' || needs.docker-build.result == 'cancelled' || needs.build-deb.result == 'cancelled' || needs.build-msi.result == 'cancelled' || needs.validate-openapi-spec.result == 'cancelled' || needs.upload-code-coverage.result == 'cancelled' || needs.check-winget-pr-template.result == 'cancelled' || needs.efcore-version-match.result == 'cancelled' || needs.pages-build.result == 'cancelled'
+        if: cancelled()
         run: dotnet release_notes_bins/Tgstation.Server.ReleaseNotes.dll --ci-check ${{ inputs.pull_request_head_sha || github.sha }} ${{ secrets.TGS_CI_GITHUB_APP_TOKEN_BASE64 }} Cancelled ${{ github.run_id }}
 
       - name: Update CI Check Run (Failure) # This is just !(cancelled || success) because failure can happen in non-needs and not trigger on any of them
-        if: (!((needs.pages-build.result == 'cancelled' || needs.docker-build.result == 'cancelled' || needs.build-deb.result == 'cancelled' || needs.build-msi.result == 'cancelled' || needs.validate-openapi-spec.result == 'cancelled' || needs.upload-code-coverage.result == 'cancelled' || needs.check-winget-pr-template.result == 'cancelled' || needs.efcore-version-match.result == 'cancelled' || needs.pages-build.result == 'cancelled') || (needs.pages-build.result == 'success' && needs.docker-build.result == 'success' && needs.build-deb.result == 'success' && needs.build-msi.result == 'success' && needs.validate-openapi-spec.result == 'success' && needs.upload-code-coverage.result == 'success' && needs.check-winget-pr-template.result == 'success' && needs.efcore-version-match.result == 'success' && needs.pages-build.result == 'success')))
+        if: (!(cancelled() || (needs.validate-openapi-spec.result == 'success' && needs.upload-code-coverage.result == 'success')))
         run: dotnet release_notes_bins/Tgstation.Server.ReleaseNotes.dll --ci-check ${{ inputs.pull_request_head_sha || github.sha }} ${{ secrets.TGS_CI_GITHUB_APP_TOKEN_BASE64 }} Failure ${{ github.run_id }}
 
-      - name: Update CI Check Run (Success)
-        if: needs.pages-build.result == 'success' && needs.docker-build.result == 'success' && needs.build-deb.result == 'success' && needs.build-msi.result == 'success' && needs.validate-openapi-spec.result == 'success' && needs.upload-code-coverage.result == 'success' && needs.check-winget-pr-template.result == 'success' && needs.efcore-version-match.result == 'success' && needs.pages-build.result == 'success'
+      - name: Update CI Check Run (Success) # Only need to check direct dependencies
+        if: needs.pages-build.result == 'success' && needs.docker-build.result == 'success' && needs.build-deb.result == 'success' && needs.build-msi.result == 'success' && needs.validate-openapi-spec.result == 'success' && needs.upload-code-coverage.result == 'success' && needs.check-winget-pr-template.result == 'success' && needs.efcore-version-match.result == 'success' && needs.ci-start-gate.result == 'success'
         run: dotnet release_notes_bins/Tgstation.Server.ReleaseNotes.dll --ci-check ${{ inputs.pull_request_head_sha || github.sha }} ${{ secrets.TGS_CI_GITHUB_APP_TOKEN_BASE64 }} Success ${{ github.run_id }}
 
       - name: Fail Job if Prerequisites Failed
-        if: (!((needs.pages-build.result == 'cancelled' || needs.docker-build.result == 'cancelled' || needs.build-deb.result == 'cancelled' || needs.build-msi.result == 'cancelled' || needs.validate-openapi-spec.result == 'cancelled' || needs.upload-code-coverage.result == 'cancelled' || needs.check-winget-pr-template.result == 'cancelled' || needs.efcore-version-match.result == 'cancelled' || needs.pages-build.result == 'cancelled') || (needs.pages-build.result == 'success' && needs.docker-build.result == 'success' && needs.build-deb.result == 'success' && needs.build-msi.result == 'success' && needs.validate-openapi-spec.result == 'success' && needs.upload-code-coverage.result == 'success' && needs.check-winget-pr-template.result == 'success' && needs.efcore-version-match.result == 'success' && needs.pages-build.result == 'success')))
+        if: (!(cancelled() || (needs.pages-build.result == 'success' && needs.docker-build.result == 'success' && needs.build-deb.result == 'success' && needs.build-msi.result == 'success' && needs.validate-openapi-spec.result == 'success' && needs.upload-code-coverage.result == 'success' && needs.check-winget-pr-template.result == 'success' && needs.efcore-version-match.result == 'success' && needs.ci-start-gate.result == 'success')))
         run: exit 1
 
   deployment-gate: