From cf0a80d03d81dfd5018fe4da5decdf631df6a07b Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 14:46:16 +0200
Subject: [PATCH 01/15] fix: derive plan path from feature.json in
 update-agent-context

When `plan_path` is omitted, prefer `.specify/feature.json`
(written by /speckit-specify) over the mtime heuristic. The
old approach picked the most recently modified `specs/*/plan.md`,
which could inject an unrelated plan into CLAUDE.md if another
spec's plan was touched after the active feature directory was
created but before its own plan.md existed.

Bash: handle both relative and absolute feature_directory values,
normalizing absolute paths back to project-relative for the
context file. Fall back to mtime only when feature.json is absent
or the derived plan.md does not yet exist.

PowerShell: same logic, PS 5.1-compatible (nested Join-Path,
IsPathRooted guard to avoid Unix Join-Path mis-joining absolute
ChildPaths, manual prefix-strip instead of GetRelativePath).

Fixes #3067
---
 .../scripts/bash/update-agent-context.sh      |  51 ++++-
 .../powershell/update-agent-context.ps1       |  63 ++++--
 .../test_update_agent_context_feature_json.py | 181 ++++++++++++++++++
 3 files changed, 271 insertions(+), 24 deletions(-)
 create mode 100644 tests/extensions/test_update_agent_context_feature_json.py

diff --git a/extensions/agent-context/scripts/bash/update-agent-context.sh b/extensions/agent-context/scripts/bash/update-agent-context.sh
index 42ce44df9a..614a0523dd 100755
--- a/extensions/agent-context/scripts/bash/update-agent-context.sh
+++ b/extensions/agent-context/scripts/bash/update-agent-context.sh
@@ -10,9 +10,9 @@
 #
 # Usage: update-agent-context.sh [plan_path]
 #
-# When `plan_path` is omitted, the script picks the most recently modified
-# `specs/*/plan.md` if any exist, otherwise emits the section without a
-# concrete plan path.
+# When `plan_path` is omitted, the script derives it from `.specify/feature.json`
+# (written by /speckit-specify). Falls back to the most recently modified
+# `specs/*/plan.md` only when feature.json is absent or its plan does not exist yet.
 
 set -euo pipefail
 
@@ -122,11 +122,41 @@ unset _cf_parts _seg
 
 PLAN_PATH="${1:-}"
 if [[ -z "$PLAN_PATH" ]]; then
-  # Pick the most recently modified plan.md one level deep (specs/<feature>/plan.md).
-  # Use find + sort by modification time to avoid ls/head fragility with
-  # spaces in paths or SIGPIPE from pipefail.
-  _plan_abs="$("$_python" - "$PROJECT_ROOT" <<'PY'
-import sys, os
+  # Prefer .specify/feature.json (written by /speckit-specify) over mtime heuristic.
+  _feature_json="$PROJECT_ROOT/.specify/feature.json"
+  if [[ -f "$_feature_json" ]]; then
+    _feature_dir="$("$_python" - "$_feature_json" <<'PY'
+import sys, json
+try:
+    d = json.load(open(sys.argv[1]))
+    print(d.get("feature_directory", ""))
+except Exception:
+    print("")
+PY
+)"
+    if [[ -n "$_feature_dir" ]]; then
+      # feature_directory may be relative or absolute (absolute paths outside PROJECT_ROOT
+      # are preserved as-is by _persist_feature_json in common.sh).
+      if [[ "$_feature_dir" == /* ]]; then
+        _candidate="$_feature_dir/plan.md"
+      else
+        _candidate="$PROJECT_ROOT/$_feature_dir/plan.md"
+      fi
+      if [[ -f "$_candidate" ]]; then
+        # Emit a PROJECT_ROOT-relative path when possible, otherwise use the absolute path.
+        if [[ "$_candidate" == "$PROJECT_ROOT/"* ]]; then
+          PLAN_PATH="${_candidate#"$PROJECT_ROOT/"}"
+        else
+          PLAN_PATH="$_candidate"
+        fi
+      fi
+    fi
+  fi
+
+  # Fall back to mtime only when feature.json is absent or its plan does not exist yet.
+  if [[ -z "$PLAN_PATH" ]]; then
+    _plan_abs="$("$_python" - "$PROJECT_ROOT" <<'PY'
+import sys
 from pathlib import Path
 specs = Path(sys.argv[1]) / "specs"
 plans = sorted(
@@ -137,8 +167,9 @@ plans = sorted(
 print(plans[0] if plans else "")
 PY
 )"
-  if [[ -n "$_plan_abs" ]]; then
-    PLAN_PATH="${_plan_abs#"$PROJECT_ROOT/"}"
+    if [[ -n "$_plan_abs" ]]; then
+      PLAN_PATH="${_plan_abs#"$PROJECT_ROOT/"}"
+    fi
   fi
 fi
 
diff --git a/extensions/agent-context/scripts/powershell/update-agent-context.ps1 b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
index dad309c03a..a4e4e79308 100644
--- a/extensions/agent-context/scripts/powershell/update-agent-context.ps1
+++ b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
@@ -9,6 +9,10 @@
 #   .specify/extensions/agent-context/agent-context-config.yml
 #
 # Usage: update-agent-context.ps1 [plan_path]
+#
+# When `plan_path` is omitted, the script derives it from `.specify/feature.json`
+# (written by /speckit-specify). Falls back to the most recently modified
+# `specs/*/plan.md` only when feature.json is absent or its plan does not exist yet.
 
 [CmdletBinding()]
 param(
@@ -166,21 +170,52 @@ if ($cm) {
 }
 
 if (-not $PlanPath) {
-    # Discover plan.md exactly one level deep (specs/<feature>/plan.md),
-    # matching the bash glob specs/*/plan.md. Wrap in try/catch so access errors under
-    # $ErrorActionPreference = 'Stop' don't abort the script.
-    try {
-        $specsDir = Join-Path $ProjectRoot 'specs'
-        $candidate = Get-ChildItem -Path $specsDir -Directory -ErrorAction SilentlyContinue |
-            ForEach-Object { Get-Item -LiteralPath (Join-Path $_.FullName 'plan.md') -ErrorAction SilentlyContinue } |
-            Where-Object { $_ } |
-            Sort-Object LastWriteTime -Descending |
-            Select-Object -First 1
-        if ($candidate) {
-            $PlanPath = [System.IO.Path]::GetRelativePath($ProjectRoot, $candidate.FullName).Replace('\','/')
+    # Prefer .specify/feature.json (written by /speckit-specify) over mtime heuristic.
+    $FeatureJson = Join-Path $ProjectRoot '.specify/feature.json'
+    if (Test-Path -LiteralPath $FeatureJson) {
+        try {
+            $fj = Get-Content -LiteralPath $FeatureJson -Raw -Encoding UTF8 | ConvertFrom-Json
+            $featureDir = $fj.feature_directory
+            if ($featureDir) {
+                # Join-Path on Unix does not treat absolute ChildPath as "wins"; check explicitly.
+                if ([System.IO.Path]::IsPathRooted($featureDir)) {
+                    $candidatePlan = Join-Path $featureDir 'plan.md'
+                } else {
+                    $candidatePlan = Join-Path (Join-Path $ProjectRoot $featureDir) 'plan.md'
+                }
+                if (Test-Path -LiteralPath $candidatePlan) {
+                    # Normalize absolute feature paths to project-relative (mirrors bash behavior).
+                    $relDir = $featureDir
+                    if ([System.IO.Path]::IsPathRooted($featureDir)) {
+                        $normRoot = $ProjectRoot.TrimEnd('\', '/') + [System.IO.Path]::DirectorySeparatorChar
+                        $normDir  = $featureDir.Replace('/', [System.IO.Path]::DirectorySeparatorChar)
+                        if ($normDir.StartsWith($normRoot, [System.StringComparison]::OrdinalIgnoreCase)) {
+                            $relDir = $normDir.Substring($normRoot.Length)
+                        }
+                    }
+                    $PlanPath = $relDir.Replace('\', '/') + '/plan.md'
+                }
+            }
+        } catch {
+            # Non-fatal: fall through to mtime heuristic.
+        }
+    }
+
+    # Fall back to mtime only when feature.json is absent or its plan does not exist yet.
+    if (-not $PlanPath) {
+        try {
+            $specsDir = Join-Path $ProjectRoot 'specs'
+            $candidate = Get-ChildItem -Path $specsDir -Directory -ErrorAction SilentlyContinue |
+                ForEach-Object { Get-Item -LiteralPath (Join-Path $_.FullName 'plan.md') -ErrorAction SilentlyContinue } |
+                Where-Object { $_ } |
+                Sort-Object LastWriteTime -Descending |
+                Select-Object -First 1
+            if ($candidate) {
+                $PlanPath = [System.IO.Path]::GetRelativePath($ProjectRoot, $candidate.FullName).Replace('\','/')
+            }
+        } catch {
+            # Non-fatal: continue without a plan path.
         }
-    } catch {
-        # Non-fatal: continue without a plan path.
     }
 }
 
diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
new file mode 100644
index 0000000000..210085fb2d
--- /dev/null
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -0,0 +1,181 @@
+"""Tests that update-agent-context.sh/.ps1 prefer feature.json over mtime."""
+
+from __future__ import annotations
+
+import json
+import os
+import shutil
+import subprocess
+import time
+from pathlib import Path
+
+import pytest
+
+from tests.conftest import requires_bash
+
+PROJECT_ROOT = Path(__file__).resolve().parent.parent.parent
+UPDATE_AGENT_CTX_SH = (
+    PROJECT_ROOT / "extensions" / "agent-context" / "scripts" / "bash" / "update-agent-context.sh"
+)
+UPDATE_AGENT_CTX_PS = (
+    PROJECT_ROOT / "extensions" / "agent-context" / "scripts" / "powershell" / "update-agent-context.ps1"
+)
+
+HAS_PWSH = shutil.which("pwsh") is not None
+_WINDOWS_POWERSHELL = (shutil.which("powershell.exe") or shutil.which("powershell")) if os.name == "nt" else None
+
+
+def _setup_project(root: Path, context_file: str = "CLAUDE.md") -> None:
+    """Write the minimal agent-context extension config."""
+    cfg_dir = root / ".specify" / "extensions" / "agent-context"
+    cfg_dir.mkdir(parents=True, exist_ok=True)
+    (cfg_dir / "agent-context-config.yml").write_text(
+        f"context_file: {context_file}\n"
+        "context_markers:\n"
+        "  start: '<!-- SPECKIT START -->'\n"
+        "  end: '<!-- SPECKIT END -->'\n",
+        encoding="utf-8",
+    )
+
+
+def _write_feature_json(root: Path, feature_directory: str) -> None:
+    specify_dir = root / ".specify"
+    specify_dir.mkdir(parents=True, exist_ok=True)
+    (specify_dir / "feature.json").write_text(
+        json.dumps({"feature_directory": feature_directory}),
+        encoding="utf-8",
+    )
+
+
+def _make_plan(root: Path, feature_dir: str, content: str = "# plan\n") -> Path:
+    p = root / feature_dir / "plan.md"
+    p.parent.mkdir(parents=True, exist_ok=True)
+    p.write_text(content, encoding="utf-8")
+    return p
+
+
+@requires_bash
+def test_bash_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
+    """feature.json points to the active feature; that plan.md is injected."""
+    _setup_project(tmp_path)
+    _make_plan(tmp_path, "specs/001-active")
+    _write_feature_json(tmp_path, "specs/001-active")
+
+    result = subprocess.run(
+        ["bash", str(UPDATE_AGENT_CTX_SH)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "specs/001-active/plan.md" in ctx
+
+
+@requires_bash
+def test_bash_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path) -> None:
+    """An older spec's plan.md modified more recently must NOT win over feature.json."""
+    _setup_project(tmp_path)
+
+    # Create active feature plan first, then touch the stale one to make it newer.
+    _make_plan(tmp_path, "specs/001-active")
+    time.sleep(0.05)
+    _make_plan(tmp_path, "specs/000-stale")
+
+    _write_feature_json(tmp_path, "specs/001-active")
+
+    result = subprocess.run(
+        ["bash", str(UPDATE_AGENT_CTX_SH)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "specs/001-active/plan.md" in ctx
+    assert "specs/000-stale/plan.md" not in ctx
+
+
+@requires_bash
+def test_bash_falls_back_to_mtime_when_feature_json_absent(tmp_path: Path) -> None:
+    """No feature.json → mtime fallback selects the most recently modified plan."""
+    _setup_project(tmp_path)
+    _make_plan(tmp_path, "specs/000-old")
+    time.sleep(0.05)
+    _make_plan(tmp_path, "specs/001-newer")
+
+    result = subprocess.run(
+        ["bash", str(UPDATE_AGENT_CTX_SH)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "specs/001-newer/plan.md" in ctx
+
+
+@requires_bash
+def test_bash_falls_back_to_mtime_when_plan_not_yet_created(tmp_path: Path) -> None:
+    """feature.json exists but plan.md not yet written → fall back to mtime."""
+    _setup_project(tmp_path)
+    _make_plan(tmp_path, "specs/000-old")
+    # feature.json points to 001-new but its plan.md doesn't exist yet
+    _write_feature_json(tmp_path, "specs/001-new")
+
+    result = subprocess.run(
+        ["bash", str(UPDATE_AGENT_CTX_SH)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "specs/000-old/plan.md" in ctx
+
+
+@pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
+def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
+    """PowerShell: feature.json points to the active feature; that plan is injected."""
+    _setup_project(tmp_path)
+    _make_plan(tmp_path, "specs/001-active")
+    _write_feature_json(tmp_path, "specs/001-active")
+
+    exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
+    result = subprocess.run(
+        [exe, "-NoProfile", "-File", str(UPDATE_AGENT_CTX_PS)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "specs/001-active/plan.md" in ctx
+
+
+@pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
+def test_ps_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path) -> None:
+    """PowerShell: stale plan touched more recently must not win over feature.json."""
+    _setup_project(tmp_path)
+    _make_plan(tmp_path, "specs/001-active")
+    time.sleep(0.05)
+    _make_plan(tmp_path, "specs/000-stale")
+    _write_feature_json(tmp_path, "specs/001-active")
+
+    exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
+    result = subprocess.run(
+        [exe, "-NoProfile", "-File", str(UPDATE_AGENT_CTX_PS)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "specs/001-active/plan.md" in ctx
+    assert "specs/000-stale/plan.md" not in ctx

From b290c03c13422cd7881ef289d4ebddc0013225ec Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 19:56:21 +0200
Subject: [PATCH 02/15] fix: address Copilot review feedback on
 update-agent-context

- bash: add explicit encoding="utf-8" to feature.json open() call
- powershell: replace GetRelativePath (.NET 5+ only) with manual
  prefix-strip in mtime fallback for PS 5.1 compatibility
- tests: add coverage for absolute feature_directory values
  (under and outside PROJECT_ROOT)
---
 .../scripts/bash/update-agent-context.sh      |  2 +-
 .../powershell/update-agent-context.ps1       |  9 +++-
 .../test_update_agent_context_feature_json.py | 46 +++++++++++++++++++
 3 files changed, 55 insertions(+), 2 deletions(-)

diff --git a/extensions/agent-context/scripts/bash/update-agent-context.sh b/extensions/agent-context/scripts/bash/update-agent-context.sh
index 614a0523dd..c10c01ee0a 100755
--- a/extensions/agent-context/scripts/bash/update-agent-context.sh
+++ b/extensions/agent-context/scripts/bash/update-agent-context.sh
@@ -128,7 +128,7 @@ if [[ -z "$PLAN_PATH" ]]; then
     _feature_dir="$("$_python" - "$_feature_json" <<'PY'
 import sys, json
 try:
-    d = json.load(open(sys.argv[1]))
+    d = json.load(open(sys.argv[1], encoding="utf-8"))
     print(d.get("feature_directory", ""))
 except Exception:
     print("")
diff --git a/extensions/agent-context/scripts/powershell/update-agent-context.ps1 b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
index a4e4e79308..c3aa3036a3 100644
--- a/extensions/agent-context/scripts/powershell/update-agent-context.ps1
+++ b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
@@ -211,7 +211,14 @@ if (-not $PlanPath) {
                 Sort-Object LastWriteTime -Descending |
                 Select-Object -First 1
             if ($candidate) {
-                $PlanPath = [System.IO.Path]::GetRelativePath($ProjectRoot, $candidate.FullName).Replace('\','/')
+                # GetRelativePath is .NET 5+ only; strip prefix manually for PS 5.1 compat.
+                $fullPath = $candidate.FullName.Replace('\', '/')
+                $normRoot = $ProjectRoot.Replace('\', '/').TrimEnd('/') + '/'
+                if ($fullPath.StartsWith($normRoot, [System.StringComparison]::OrdinalIgnoreCase)) {
+                    $PlanPath = $fullPath.Substring($normRoot.Length)
+                } else {
+                    $PlanPath = $fullPath
+                }
             }
         } catch {
             # Non-fatal: continue without a plan path.
diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 210085fb2d..dff1e954c6 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -138,6 +138,52 @@ def test_bash_falls_back_to_mtime_when_plan_not_yet_created(tmp_path: Path) -> N
     assert "specs/000-old/plan.md" in ctx
 
 
+@requires_bash
+def test_bash_absolute_feature_dir_under_project_root(tmp_path: Path) -> None:
+    """Absolute feature_directory under PROJECT_ROOT → project-relative path in context."""
+    _setup_project(tmp_path)
+    _make_plan(tmp_path, "specs/001-active")
+    # Write absolute path to feature.json
+    _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
+
+    result = subprocess.run(
+        ["bash", str(UPDATE_AGENT_CTX_SH)],
+        cwd=tmp_path,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+    # Must be project-relative, not machine-specific absolute
+    assert "specs/001-active/plan.md" in ctx
+    assert str(tmp_path) not in ctx
+
+
+@requires_bash
+def test_bash_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
+    """Absolute feature_directory outside PROJECT_ROOT → absolute path preserved in context."""
+    project = tmp_path / "project"
+    external = tmp_path / "external" / "001-feature"
+    project.mkdir()
+    external.mkdir(parents=True)
+    (external / "plan.md").write_text("# plan\n", encoding="utf-8")
+
+    _setup_project(project)
+    _write_feature_json(project, str(external))
+
+    result = subprocess.run(
+        ["bash", str(UPDATE_AGENT_CTX_SH)],
+        cwd=project,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (project / "CLAUDE.md").read_text(encoding="utf-8")
+    assert str(external) + "/plan.md" in ctx
+
+
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
 def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     """PowerShell: feature.json points to the active feature; that plan is injected."""

From d710b6275abcf66ffb122d41f68ec4c48cb6c296 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 20:07:28 +0200
Subject: [PATCH 03/15] Potential fix for pull request finding

Co-authored-by: Copilot Autofix powered by AI <175728472+Copilot@users.noreply.github.com>
---
 .../extensions/test_update_agent_context_feature_json.py  | 8 +++++---
 1 file changed, 5 insertions(+), 3 deletions(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index dff1e954c6..1e341a8ee5 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -79,9 +79,11 @@ def test_bash_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path)
     _setup_project(tmp_path)
 
     # Create active feature plan first, then touch the stale one to make it newer.
-    _make_plan(tmp_path, "specs/001-active")
-    time.sleep(0.05)
-    _make_plan(tmp_path, "specs/000-stale")
+    active = _make_plan(tmp_path, "specs/001-active")
+    stale = _make_plan(tmp_path, "specs/000-stale")
+    now = time.time()
+    os.utime(active, (now - 10, now - 10))
+    os.utime(stale, (now, now))
 
     _write_feature_json(tmp_path, "specs/001-active")
 

From b2aee0350507d5c90ae7aaa89ba11e1b65a567ac Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 20:08:52 +0200
Subject: [PATCH 04/15] test: replace time.sleep with os.utime and strengthen
 PS normalization assertion

---
 .../test_update_agent_context_feature_json.py | 25 ++++++++++++-------
 1 file changed, 16 insertions(+), 9 deletions(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 1e341a8ee5..90104172f9 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -104,9 +104,11 @@ def test_bash_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path)
 def test_bash_falls_back_to_mtime_when_feature_json_absent(tmp_path: Path) -> None:
     """No feature.json → mtime fallback selects the most recently modified plan."""
     _setup_project(tmp_path)
-    _make_plan(tmp_path, "specs/000-old")
-    time.sleep(0.05)
-    _make_plan(tmp_path, "specs/001-newer")
+    old = _make_plan(tmp_path, "specs/000-old")
+    newer = _make_plan(tmp_path, "specs/001-newer")
+    now = time.time()
+    os.utime(old, (now - 10, now - 10))
+    os.utime(newer, (now, now))
 
     result = subprocess.run(
         ["bash", str(UPDATE_AGENT_CTX_SH)],
@@ -188,10 +190,11 @@ def test_bash_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
 
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
 def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
-    """PowerShell: feature.json points to the active feature; that plan is injected."""
+    """PowerShell: absolute feature_directory under project root is normalized to relative path."""
     _setup_project(tmp_path)
     _make_plan(tmp_path, "specs/001-active")
-    _write_feature_json(tmp_path, "specs/001-active")
+    # Use absolute path to exercise the normalization code path
+    _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
 
     exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
     result = subprocess.run(
@@ -203,16 +206,20 @@ def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     )
     assert result.returncode == 0, result.stderr + result.stdout
     ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
-    assert "specs/001-active/plan.md" in ctx
+    # Must be project-relative, not machine-specific absolute
+    assert "at specs/001-active/plan.md" in ctx
+    assert str(tmp_path) not in ctx
 
 
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
 def test_ps_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path) -> None:
     """PowerShell: stale plan touched more recently must not win over feature.json."""
     _setup_project(tmp_path)
-    _make_plan(tmp_path, "specs/001-active")
-    time.sleep(0.05)
-    _make_plan(tmp_path, "specs/000-stale")
+    active = _make_plan(tmp_path, "specs/001-active")
+    stale = _make_plan(tmp_path, "specs/000-stale")
+    now = time.time()
+    os.utime(active, (now - 10, now - 10))
+    os.utime(stale, (now, now))
     _write_feature_json(tmp_path, "specs/001-active")
 
     exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL

From 9940cdbebff731f2399ecbfc9eb206ab1f578da0 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 20:52:20 +0200
Subject: [PATCH 05/15] Apply suggestions from code review

Co-authored-by: Copilot Autofix powered by AI <175728472+Copilot@users.noreply.github.com>
---
 extensions/agent-context/scripts/bash/update-agent-context.sh    | 1 +
 .../agent-context/scripts/powershell/update-agent-context.ps1    | 1 +
 2 files changed, 2 insertions(+)

diff --git a/extensions/agent-context/scripts/bash/update-agent-context.sh b/extensions/agent-context/scripts/bash/update-agent-context.sh
index c10c01ee0a..8b072b0dcd 100755
--- a/extensions/agent-context/scripts/bash/update-agent-context.sh
+++ b/extensions/agent-context/scripts/bash/update-agent-context.sh
@@ -135,6 +135,7 @@ except Exception:
 PY
 )"
     if [[ -n "$_feature_dir" ]]; then
+      _feature_dir="${_feature_dir%/}"
       # feature_directory may be relative or absolute (absolute paths outside PROJECT_ROOT
       # are preserved as-is by _persist_feature_json in common.sh).
       if [[ "$_feature_dir" == /* ]]; then
diff --git a/extensions/agent-context/scripts/powershell/update-agent-context.ps1 b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
index c3aa3036a3..6843df5bb3 100644
--- a/extensions/agent-context/scripts/powershell/update-agent-context.ps1
+++ b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
@@ -176,6 +176,7 @@ if (-not $PlanPath) {
         try {
             $fj = Get-Content -LiteralPath $FeatureJson -Raw -Encoding UTF8 | ConvertFrom-Json
             $featureDir = $fj.feature_directory
+            if ($featureDir -is [string]) { $featureDir = $featureDir.TrimEnd('\\', '/') }
             if ($featureDir) {
                 # Join-Path on Unix does not treat absolute ChildPath as "wins"; check explicitly.
                 if ([System.IO.Path]::IsPathRooted($featureDir)) {

From be127bdbd87eb31e5c4dfb86993b51ef5c135b96 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 20:59:19 +0200
Subject: [PATCH 06/15] Potential fix for pull request finding

Co-authored-by: Copilot Autofix powered by AI <175728472+Copilot@users.noreply.github.com>
---
 .../agent-context/scripts/powershell/update-agent-context.ps1 | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/extensions/agent-context/scripts/powershell/update-agent-context.ps1 b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
index 6843df5bb3..4dfdea24d9 100644
--- a/extensions/agent-context/scripts/powershell/update-agent-context.ps1
+++ b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
@@ -176,8 +176,8 @@ if (-not $PlanPath) {
         try {
             $fj = Get-Content -LiteralPath $FeatureJson -Raw -Encoding UTF8 | ConvertFrom-Json
             $featureDir = $fj.feature_directory
-            if ($featureDir -is [string]) { $featureDir = $featureDir.TrimEnd('\\', '/') }
-            if ($featureDir) {
+            if ($featureDir -isnot [string]) { $featureDir = $null }
+            if ($featureDir) { $featureDir = $featureDir.TrimEnd('\\', '/') }
                 # Join-Path on Unix does not treat absolute ChildPath as "wins"; check explicitly.
                 if ([System.IO.Path]::IsPathRooted($featureDir)) {
                     $candidatePlan = Join-Path $featureDir 'plan.md'

From 80b96c8b99d8bd7fae85becfbf0991eca5067818 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 21:04:43 +0200
Subject: [PATCH 07/15] fix: normalize trailing slash and guard non-string
 feature_directory in PS script

---
 .../scripts/powershell/update-agent-context.ps1           | 8 ++++++--
 1 file changed, 6 insertions(+), 2 deletions(-)

diff --git a/extensions/agent-context/scripts/powershell/update-agent-context.ps1 b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
index 4dfdea24d9..9e7dcac298 100644
--- a/extensions/agent-context/scripts/powershell/update-agent-context.ps1
+++ b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
@@ -176,8 +176,12 @@ if (-not $PlanPath) {
         try {
             $fj = Get-Content -LiteralPath $FeatureJson -Raw -Encoding UTF8 | ConvertFrom-Json
             $featureDir = $fj.feature_directory
-            if ($featureDir -isnot [string]) { $featureDir = $null }
-            if ($featureDir) { $featureDir = $featureDir.TrimEnd('\\', '/') }
+            if ($featureDir -isnot [string] -or -not $featureDir) {
+                $featureDir = $null
+            } else {
+                $featureDir = $featureDir.TrimEnd('\', '/')
+            }
+            if ($featureDir) {
                 # Join-Path on Unix does not treat absolute ChildPath as "wins"; check explicitly.
                 if ([System.IO.Path]::IsPathRooted($featureDir)) {
                     $candidatePlan = Join-Path $featureDir 'plan.md'

From 11530c2a5160c2d0959017ce394d12ae513da65f Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 21:14:44 +0200
Subject: [PATCH 08/15] Fix: use .resolve().as_posix().

Valid. The PS tests run on Windows where str(tmp_path) uses backslashes, but the PS script normalizes output to forward slashes. Assertions like assert str(tmp_path) not in ctx become false negatives on Windows CI.

Co-authored-by: Copilot Autofix powered by AI <175728472+Copilot@users.noreply.github.com>
---
 tests/extensions/test_update_agent_context_feature_json.py | 5 ++---
 1 file changed, 2 insertions(+), 3 deletions(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 90104172f9..26b2df8180 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -185,7 +185,7 @@ def test_bash_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
     )
     assert result.returncode == 0, result.stderr + result.stdout
     ctx = (project / "CLAUDE.md").read_text(encoding="utf-8")
-    assert str(external) + "/plan.md" in ctx
+    assert (external / "plan.md").resolve().as_posix() in ctx
 
 
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
@@ -208,8 +208,7 @@ def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
     # Must be project-relative, not machine-specific absolute
     assert "at specs/001-active/plan.md" in ctx
-    assert str(tmp_path) not in ctx
-
+    assert tmp_path.resolve().as_posix() not in ctx
 
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
 def test_ps_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path) -> None:

From 870e7ec714f69e2fe4875a72d086e1b1166d8c5d Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 21:37:29 +0200
Subject: [PATCH 09/15] fix: use context manager for feature.json open() in
 bash heredoc

---
 extensions/agent-context/scripts/bash/update-agent-context.sh | 3 ++-
 1 file changed, 2 insertions(+), 1 deletion(-)

diff --git a/extensions/agent-context/scripts/bash/update-agent-context.sh b/extensions/agent-context/scripts/bash/update-agent-context.sh
index 8b072b0dcd..bc628da1fb 100755
--- a/extensions/agent-context/scripts/bash/update-agent-context.sh
+++ b/extensions/agent-context/scripts/bash/update-agent-context.sh
@@ -128,7 +128,8 @@ if [[ -z "$PLAN_PATH" ]]; then
     _feature_dir="$("$_python" - "$_feature_json" <<'PY'
 import sys, json
 try:
-    d = json.load(open(sys.argv[1], encoding="utf-8"))
+    with open(sys.argv[1], encoding="utf-8") as fh:
+        d = json.load(fh)
     print(d.get("feature_directory", ""))
 except Exception:
     print("")

From 93dda104e94ce6f5bce23cf4ee8212bfec95b28d Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 21:43:14 +0200
Subject: [PATCH 10/15] test: add PS coverage for absolute feature_directory
 outside project root

---
 .../test_update_agent_context_feature_json.py | 25 +++++++++++++++++++
 1 file changed, 25 insertions(+)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 26b2df8180..7bca88b5f1 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -233,3 +233,28 @@ def test_ps_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path) -
     ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
     assert "specs/001-active/plan.md" in ctx
     assert "specs/000-stale/plan.md" not in ctx
+
+
+@pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
+def test_ps_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
+    """PowerShell: absolute feature_directory outside project root → absolute path preserved."""
+    project = tmp_path / "project"
+    external = tmp_path / "external" / "001-feature"
+    project.mkdir()
+    external.mkdir(parents=True)
+    (external / "plan.md").write_text("# plan\n", encoding="utf-8")
+
+    _setup_project(project)
+    _write_feature_json(project, str(external))
+
+    exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
+    result = subprocess.run(
+        [exe, "-NoProfile", "-File", str(UPDATE_AGENT_CTX_PS)],
+        cwd=project,
+        capture_output=True,
+        text=True,
+        check=False,
+    )
+    assert result.returncode == 0, result.stderr + result.stdout
+    ctx = (project / "CLAUDE.md").read_text(encoding="utf-8")
+    assert external.resolve().as_posix() + "/plan.md" in ctx

From dc1c0fa873114272577eaa0202584ebfc59c8677 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 21:54:16 +0200
Subject: [PATCH 11/15] fix: guard null feature_directory, re-check empty after
 trailing-slash strip, fix blank line

---
 .../agent-context/scripts/bash/update-agent-context.sh       | 5 +++--
 tests/extensions/test_update_agent_context_feature_json.py   | 1 +
 2 files changed, 4 insertions(+), 2 deletions(-)

diff --git a/extensions/agent-context/scripts/bash/update-agent-context.sh b/extensions/agent-context/scripts/bash/update-agent-context.sh
index bc628da1fb..67b1a2867a 100755
--- a/extensions/agent-context/scripts/bash/update-agent-context.sh
+++ b/extensions/agent-context/scripts/bash/update-agent-context.sh
@@ -130,13 +130,14 @@ import sys, json
 try:
     with open(sys.argv[1], encoding="utf-8") as fh:
         d = json.load(fh)
-    print(d.get("feature_directory", ""))
+    val = d.get("feature_directory", "")
+    print(val if isinstance(val, str) else "")
 except Exception:
     print("")
 PY
 )"
+    _feature_dir="${_feature_dir%/}"
     if [[ -n "$_feature_dir" ]]; then
-      _feature_dir="${_feature_dir%/}"
       # feature_directory may be relative or absolute (absolute paths outside PROJECT_ROOT
       # are preserved as-is by _persist_feature_json in common.sh).
       if [[ "$_feature_dir" == /* ]]; then
diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 7bca88b5f1..b26def956d 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -210,6 +210,7 @@ def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     assert "at specs/001-active/plan.md" in ctx
     assert tmp_path.resolve().as_posix() not in ctx
 
+
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
 def test_ps_ignores_newer_stale_plan_when_feature_json_present(tmp_path: Path) -> None:
     """PowerShell: stale plan touched more recently must not win over feature.json."""

From 1808ce7729cb8567c474aa14ac612628d9e5b7cd Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 22:00:31 +0200
Subject: [PATCH 12/15] test: add stale plan to absolute-path tests so
 feature.json preference is actually exercised

---
 .../test_update_agent_context_feature_json.py  | 18 ++++++++++++++----
 1 file changed, 14 insertions(+), 4 deletions(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index b26def956d..448036f792 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -146,8 +146,12 @@ def test_bash_falls_back_to_mtime_when_plan_not_yet_created(tmp_path: Path) -> N
 def test_bash_absolute_feature_dir_under_project_root(tmp_path: Path) -> None:
     """Absolute feature_directory under PROJECT_ROOT → project-relative path in context."""
     _setup_project(tmp_path)
-    _make_plan(tmp_path, "specs/001-active")
-    # Write absolute path to feature.json
+    active = _make_plan(tmp_path, "specs/001-active")
+    stale = _make_plan(tmp_path, "specs/000-stale")
+    now = time.time()
+    os.utime(active, (now - 10, now - 10))
+    os.utime(stale, (now, now))
+    # Write absolute path to feature.json — mtime would pick 000-stale without it
     _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
 
     result = subprocess.run(
@@ -161,6 +165,7 @@ def test_bash_absolute_feature_dir_under_project_root(tmp_path: Path) -> None:
     ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
     # Must be project-relative, not machine-specific absolute
     assert "specs/001-active/plan.md" in ctx
+    assert "specs/000-stale/plan.md" not in ctx
     assert str(tmp_path) not in ctx
 
 
@@ -192,8 +197,12 @@ def test_bash_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
 def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     """PowerShell: absolute feature_directory under project root is normalized to relative path."""
     _setup_project(tmp_path)
-    _make_plan(tmp_path, "specs/001-active")
-    # Use absolute path to exercise the normalization code path
+    active = _make_plan(tmp_path, "specs/001-active")
+    stale = _make_plan(tmp_path, "specs/000-stale")
+    now = time.time()
+    os.utime(active, (now - 10, now - 10))
+    os.utime(stale, (now, now))
+    # Write absolute path to feature.json — mtime would pick 000-stale without it
     _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
 
     exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
@@ -208,6 +217,7 @@ def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     ctx = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
     # Must be project-relative, not machine-specific absolute
     assert "at specs/001-active/plan.md" in ctx
+    assert "specs/000-stale/plan.md" not in ctx
     assert tmp_path.resolve().as_posix() not in ctx
 
 

From b24279b20f611e4f8daf38d6d9650bbcead7ce7d Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 22:09:35 +0200
Subject: [PATCH 13/15] test: convert absolute paths to MSYS2 style for
 Git-for-Windows bash compatibility

---
 .../test_update_agent_context_feature_json.py | 21 ++++++++++++++++---
 1 file changed, 18 insertions(+), 3 deletions(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 448036f792..2124556fc2 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -47,6 +47,21 @@ def _write_feature_json(root: Path, feature_directory: str) -> None:
     )
 
 
+def _to_bash_path(p: Path) -> str:
+    """Return a path string usable inside Git-for-Windows bash.
+
+    On Windows, Python paths use drive letters (C:\\...) but Git bash (MSYS2)
+    expects POSIX-style paths (/c/...). On all other platforms the path is
+    returned unchanged.
+    """
+    if os.name != "nt":
+        return str(p.resolve())
+    posix = p.resolve().as_posix()  # C:/foo/bar
+    if len(posix) >= 2 and posix[1] == ":":
+        return "/" + posix[0].lower() + posix[2:]
+    return posix
+
+
 def _make_plan(root: Path, feature_dir: str, content: str = "# plan\n") -> Path:
     p = root / feature_dir / "plan.md"
     p.parent.mkdir(parents=True, exist_ok=True)
@@ -152,7 +167,7 @@ def test_bash_absolute_feature_dir_under_project_root(tmp_path: Path) -> None:
     os.utime(active, (now - 10, now - 10))
     os.utime(stale, (now, now))
     # Write absolute path to feature.json — mtime would pick 000-stale without it
-    _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
+    _write_feature_json(tmp_path, _to_bash_path(tmp_path / "specs" / "001-active"))
 
     result = subprocess.run(
         ["bash", str(UPDATE_AGENT_CTX_SH)],
@@ -179,7 +194,7 @@ def test_bash_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
     (external / "plan.md").write_text("# plan\n", encoding="utf-8")
 
     _setup_project(project)
-    _write_feature_json(project, str(external))
+    _write_feature_json(project, _to_bash_path(external))
 
     result = subprocess.run(
         ["bash", str(UPDATE_AGENT_CTX_SH)],
@@ -203,7 +218,7 @@ def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     os.utime(active, (now - 10, now - 10))
     os.utime(stale, (now, now))
     # Write absolute path to feature.json — mtime would pick 000-stale without it
-    _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
+    _write_feature_json(tmp_path, _to_bash_path(tmp_path / "specs" / "001-active"))
 
     exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
     result = subprocess.run(

From 855550e15507f50d62f7c1fbbe498089aa327b66 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 22:13:37 +0200
Subject: [PATCH 14/15] fix: revert PS test to native path, fix bash
 outside-root assertion for Git bash

---
 tests/extensions/test_update_agent_context_feature_json.py | 5 +++--
 1 file changed, 3 insertions(+), 2 deletions(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index 2124556fc2..a0ed55a255 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -205,7 +205,7 @@ def test_bash_absolute_feature_dir_outside_project_root(tmp_path: Path) -> None:
     )
     assert result.returncode == 0, result.stderr + result.stdout
     ctx = (project / "CLAUDE.md").read_text(encoding="utf-8")
-    assert (external / "plan.md").resolve().as_posix() in ctx
+    assert _to_bash_path(external) + "/plan.md" in ctx
 
 
 @pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
@@ -218,7 +218,8 @@ def test_ps_uses_feature_json_when_plan_exists(tmp_path: Path) -> None:
     os.utime(active, (now - 10, now - 10))
     os.utime(stale, (now, now))
     # Write absolute path to feature.json — mtime would pick 000-stale without it
-    _write_feature_json(tmp_path, _to_bash_path(tmp_path / "specs" / "001-active"))
+    # Use native str() here: PowerShell expects Windows-native paths, not MSYS2 /c/... form
+    _write_feature_json(tmp_path, str(tmp_path / "specs" / "001-active"))
 
     exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
     result = subprocess.run(

From 8e3d78a83bde0b0afbd8fb3c13043d0d0c7c4227 Mon Sep 17 00:00:00 2001
From: Amirreza Alibeigi <amirreza225@users.noreply.github.com>
Date: Fri, 19 Jun 2026 22:17:42 +0200
Subject: [PATCH 15/15] fix: use _to_bash_path in not-in assertion for Git bash
 Windows compat

---
 tests/extensions/test_update_agent_context_feature_json.py | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/tests/extensions/test_update_agent_context_feature_json.py b/tests/extensions/test_update_agent_context_feature_json.py
index a0ed55a255..6fcdd73ffe 100644
--- a/tests/extensions/test_update_agent_context_feature_json.py
+++ b/tests/extensions/test_update_agent_context_feature_json.py
@@ -181,7 +181,7 @@ def test_bash_absolute_feature_dir_under_project_root(tmp_path: Path) -> None:
     # Must be project-relative, not machine-specific absolute
     assert "specs/001-active/plan.md" in ctx
     assert "specs/000-stale/plan.md" not in ctx
-    assert str(tmp_path) not in ctx
+    assert _to_bash_path(tmp_path) not in ctx
 
 
 @requires_bash