From bf71d6474605d3e94cbc3cb773c5220c0ae5e3a0 Mon Sep 17 00:00:00 2001
From: Neil <4138956+nwparker@users.noreply.github.com>
Date: Thu, 15 Oct 2026 12:29:59 -0700
Subject: [PATCH] [CI] Group skill update checks by operating system (#29021)

---
 .github/workflows/skill-update-roundtrip.yml | 60 +++++++++++++++++---
 1 file changed, 51 insertions(+), 9 deletions(-)

diff --git a/.github/workflows/skill-update-roundtrip.yml b/.github/workflows/skill-update-roundtrip.yml
index 490b45483b5..7115ea38e28 100644
--- a/.github/workflows/skill-update-roundtrip.yml
+++ b/.github/workflows/skill-update-roundtrip.yml
@@ -32,32 +32,74 @@ jobs:
       fail-fast: false
       matrix:
         os: [macos-latest, ubuntu-latest, windows-latest]
-        shape: [symlink, copy]
-        autocrlf: ['false', 'true']
         # Why: `pinned` runs the skills CLI version Orca ships (SKILLS_CLI_VERSION).
         skills-cli: [pinned]
         include:
           - os: ubuntu-latest
-            shape: symlink
-            autocrlf: 'false'
             skills-cli: latest
     continue-on-error: ${{ matrix.skills-cli == 'latest' }}
     runs-on: ${{ matrix.os }}
     steps:
       - uses: actions/checkout@v6
+        id: checkout
         with:
           persist-credentials: false
       - uses: actions/setup-node@v6
+        id: node
         with:
           node-version-file: package.json
-      - name: Verify the pinned add replaces stale copies
+      - name: Verify pinned symlink placement with autocrlf false
+        if: ${{ !cancelled() && matrix.skills-cli == 'pinned' && steps.checkout.outcome == 'success' && steps.node.outcome == 'success' }}
         env:
           GITHUB_TOKEN: ${{ github.token }}
           SKILL_UPDATE_SOURCE: ${{ github.event.pull_request.head.repo.full_name || github.repository }}
-          # A commit, the same kind of ref Orca pins official skills to.
           SKILL_UPDATE_REF: ${{ github.event.pull_request.head.sha || github.sha }}
         run: >-
           node config/scripts/verify-skill-update-roundtrip.mjs
-          ${{ matrix.skills-cli == 'latest' && '--cli=latest' || '' }}
-          --autocrlf=${{ matrix.autocrlf }}
-          --shape=${{ matrix.shape }}
+          --autocrlf=false
+          --shape=symlink
+
+      - name: Verify pinned symlink placement with autocrlf true
+        if: ${{ !cancelled() && matrix.skills-cli == 'pinned' && steps.checkout.outcome == 'success' && steps.node.outcome == 'success' }}
+        env:
+          GITHUB_TOKEN: ${{ github.token }}
+          SKILL_UPDATE_SOURCE: ${{ github.event.pull_request.head.repo.full_name || github.repository }}
+          SKILL_UPDATE_REF: ${{ github.event.pull_request.head.sha || github.sha }}
+        run: >-
+          node config/scripts/verify-skill-update-roundtrip.mjs
+          --autocrlf=true
+          --shape=symlink
+
+      - name: Verify pinned copy placement with autocrlf false
+        if: ${{ !cancelled() && matrix.skills-cli == 'pinned' && steps.checkout.outcome == 'success' && steps.node.outcome == 'success' }}
+        env:
+          GITHUB_TOKEN: ${{ github.token }}
+          SKILL_UPDATE_SOURCE: ${{ github.event.pull_request.head.repo.full_name || github.repository }}
+          SKILL_UPDATE_REF: ${{ github.event.pull_request.head.sha || github.sha }}
+        run: >-
+          node config/scripts/verify-skill-update-roundtrip.mjs
+          --autocrlf=false
+          --shape=copy
+
+      - name: Verify pinned copy placement with autocrlf true
+        if: ${{ !cancelled() && matrix.skills-cli == 'pinned' && steps.checkout.outcome == 'success' && steps.node.outcome == 'success' }}
+        env:
+          GITHUB_TOKEN: ${{ github.token }}
+          SKILL_UPDATE_SOURCE: ${{ github.event.pull_request.head.repo.full_name || github.repository }}
+          SKILL_UPDATE_REF: ${{ github.event.pull_request.head.sha || github.sha }}
+        run: >-
+          node config/scripts/verify-skill-update-roundtrip.mjs
+          --autocrlf=true
+          --shape=copy
+
+      - name: Preview latest CLI with symlink placement and autocrlf false
+        if: matrix.skills-cli == 'latest'
+        env:
+          GITHUB_TOKEN: ${{ github.token }}
+          SKILL_UPDATE_SOURCE: ${{ github.event.pull_request.head.repo.full_name || github.repository }}
+          SKILL_UPDATE_REF: ${{ github.event.pull_request.head.sha || github.sha }}
+        run: >-
+          node config/scripts/verify-skill-update-roundtrip.mjs
+          --cli=latest
+          --autocrlf=false
+          --shape=symlink