diff --git a/.github/actions/headroom-e2e-setup/action.yml b/.github/actions/headroom-e2e-setup/action.yml
new file mode 100644
index 000000000..2faf79c64
--- /dev/null
+++ b/.github/actions/headroom-e2e-setup/action.yml
@@ -0,0 +1,66 @@
+name: Headroom e2e setup
+description: >-
+  Checkout-agnostic setup shared by native e2e workflows (init, install, wrap).
+  Installs Python, installs headroom in editable mode, and (optionally) drops
+  a noop shim onto PATH so ``headroom init -g <target>`` can detect a tool
+  that isn't actually installed on the runner.
+inputs:
+  python-version:
+    description: Python version to install
+    required: false
+    default: "3.11"
+  shim-target:
+    description: >-
+      Name of the shim to drop on PATH (e.g. ``claude``, ``codex``). Leave
+      empty to skip shim creation.
+    required: false
+    default: ""
+outputs:
+  shim-dir:
+    description: Absolute path to the directory containing the dropped shim
+    value: ${{ steps.shim.outputs.shim-dir }}
+runs:
+  using: composite
+  steps:
+    - name: Set up Python ${{ inputs.python-version }}
+      uses: actions/setup-python@v5
+      with:
+        python-version: ${{ inputs.python-version }}
+
+    - name: Install headroom (editable, core deps only)
+      shell: bash
+      run: |
+        python -m pip install --upgrade pip
+        # ``init`` doesn't need the proxy extras; install the base package.
+        pip install -e .
+
+    - name: Drop shim (POSIX)
+      if: ${{ inputs.shim-target != '' && runner.os != 'Windows' }}
+      id: shim-posix
+      shell: bash
+      run: |
+        shim_dir="${RUNNER_TEMP}/headroom-e2e-shims"
+        bash e2e/_lib/make_shim.sh "${{ inputs.shim-target }}" "$shim_dir"
+        echo "$shim_dir" >> "$GITHUB_PATH"
+        echo "shim-dir=$shim_dir" >> "$GITHUB_OUTPUT"
+
+    - name: Drop shim (Windows)
+      if: ${{ inputs.shim-target != '' && runner.os == 'Windows' }}
+      id: shim-windows
+      shell: pwsh
+      run: |
+        $shimDir = Join-Path $env:RUNNER_TEMP "headroom-e2e-shims"
+        & pwsh -File e2e/_lib/make_shim.ps1 -Name "${{ inputs.shim-target }}" -Dir $shimDir
+        Add-Content -Path $env:GITHUB_PATH -Value $shimDir
+        "shim-dir=$shimDir" | Out-File -FilePath $env:GITHUB_OUTPUT -Append
+
+    - name: Export shim dir to job output
+      if: ${{ inputs.shim-target != '' }}
+      id: shim
+      shell: bash
+      run: |
+        if [ "${{ runner.os }}" = "Windows" ]; then
+          echo "shim-dir=${{ steps.shim-windows.outputs.shim-dir }}" >> "$GITHUB_OUTPUT"
+        else
+          echo "shim-dir=${{ steps.shim-posix.outputs.shim-dir }}" >> "$GITHUB_OUTPUT"
+        fi
diff --git a/.github/workflows/init-native-e2e.yml b/.github/workflows/init-native-e2e.yml
new file mode 100644
index 000000000..a355b4f70
--- /dev/null
+++ b/.github/workflows/init-native-e2e.yml
@@ -0,0 +1,121 @@
+name: Init Native E2E
+
+# Cross-platform (linux / macos / windows) smoke tests for the per-subcommand
+# ``headroom init -g <target>`` flows. Each matrix cell drops a noop shim for
+# the target agent onto PATH and asserts ``headroom init -g <target>``
+# succeeds, writes the expected settings file, and (for claude/codex) places
+# hooks in the right place.
+#
+# Deliberately scoped to pull_request + push-to-main + workflow_dispatch to
+# avoid bloating CI minutes on every push to every feature branch. The Docker
+# init-e2e.yml still runs on every PR and provides the deeper functional
+# coverage; this workflow exists to catch platform-specific bugs (Windows
+# path separators, macos keychain prompts, PowerShell-vs-bash hook matchers)
+# that the single-platform Docker suite can miss.
+#
+# Extending to other commands (``headroom install``, ``headroom wrap``) is
+# expected to be a near-copy of this file. The shared composite action at
+# ``.github/actions/headroom-e2e-setup`` absorbs the Python + shim setup so
+# each per-command workflow only supplies its matrix and assertion steps.
+
+on:
+  pull_request:
+    branches: [main]
+    paths:
+      - "headroom/cli/init.py"
+      - "headroom/install/**"
+      - "e2e/_lib/**"
+      - "e2e/init/**"
+      - ".github/actions/headroom-e2e-setup/**"
+      - ".github/workflows/init-native-e2e.yml"
+  push:
+    branches: [main]
+  workflow_dispatch:
+
+jobs:
+  init-native:
+    runs-on: ${{ matrix.os }}
+    timeout-minutes: 15
+    strategy:
+      fail-fast: false
+      matrix:
+        os: [ubuntu-latest, macos-latest, windows-latest]
+        target: [claude, codex, copilot, openclaw]
+        exclude:
+          # openclaw delegates to ``headroom wrap openclaw`` which needs a
+          # running OpenClaw CLI; it can't be shimmed cheaply, so it's
+          # covered by the bundled Docker e2e instead.
+          - target: openclaw
+
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Setup (shim=${{ matrix.target }})
+        uses: ./.github/actions/headroom-e2e-setup
+        with:
+          python-version: "3.11"
+          shim-target: ${{ matrix.target }}
+
+      - name: Verify shim is on PATH
+        shell: bash
+        run: |
+          which "${{ matrix.target }}"
+
+      - name: Run headroom init -g ${{ matrix.target }}
+        shell: bash
+        run: |
+          set -euo pipefail
+          headroom init -g "${{ matrix.target }}"
+
+      - name: Assert settings file (POSIX)
+        if: runner.os != 'Windows'
+        shell: bash
+        run: |
+          set -euo pipefail
+          case "${{ matrix.target }}" in
+            claude)
+              test -f "$HOME/.claude/settings.json"
+              grep -q "ANTHROPIC_BASE_URL" "$HOME/.claude/settings.json"
+              ;;
+            codex)
+              test -f "$HOME/.codex/config.toml"
+              test -f "$HOME/.codex/hooks.json"
+              grep -q "headroom" "$HOME/.codex/config.toml"
+              ;;
+            copilot)
+              test -f "$HOME/.copilot/config.json"
+              grep -q "SessionStart" "$HOME/.copilot/config.json"
+              ;;
+          esac
+
+      - name: Assert settings file (Windows)
+        if: runner.os == 'Windows'
+        shell: pwsh
+        run: |
+          $ErrorActionPreference = "Stop"
+          $home_ = $env:USERPROFILE
+          switch ("${{ matrix.target }}") {
+            "claude" {
+              $p = Join-Path $home_ ".claude\settings.json"
+              if (-not (Test-Path $p)) { throw "Missing $p" }
+              if (-not ((Get-Content $p -Raw) -match "ANTHROPIC_BASE_URL")) {
+                throw "settings.json missing ANTHROPIC_BASE_URL"
+              }
+            }
+            "codex" {
+              $c = Join-Path $home_ ".codex\config.toml"
+              $h = Join-Path $home_ ".codex\hooks.json"
+              if (-not (Test-Path $c)) { throw "Missing $c" }
+              if (-not (Test-Path $h)) { throw "Missing $h" }
+              if (-not ((Get-Content $c -Raw) -match "headroom")) {
+                throw "config.toml missing headroom provider"
+              }
+            }
+            "copilot" {
+              $p = Join-Path $home_ ".copilot\config.json"
+              if (-not (Test-Path $p)) { throw "Missing $p" }
+              if (-not ((Get-Content $p -Raw) -match "SessionStart")) {
+                throw "copilot config missing SessionStart hooks"
+              }
+            }
+          }