fix: find plans in nested spec directories (#3405)

* fix: find plans in nested spec directories

The agent-context mtime fallback used a one-level specs/*/plan.md
glob, so scoped layouts (specs/<scope>/<feature>/plan.md via
SPECIFY_FEATURE_DIRECTORY) never matched and the SPECKIT block was
written without a plan path. Recurse in both script variants and
update the command doc wording.

Fixes #3024

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

* refactor: pick newest plan with max(), align doc wording

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

---------

Co-authored-by: Copilot <223556219+Copilot@users.noreply.github.com>

extensions/agent-context/commands/speckit.agent-context.update.md

@@ -15,7 +15,7 @@ The script reads the agent-context extension config at
 - `context_files` — optional project-relative paths for multiple coding agent context files. When non-empty, the script updates each listed file and the list takes precedence over `context_file`.
 - `context_markers.start` / `.end` — the delimiters surrounding the managed section. Defaults to `<!-- SPECKIT START -->` and `<!-- SPECKIT END -->` when the field is missing.
 
-It then creates, replaces, or appends the managed block so that the section points at the most recent plan path when one can be discovered (`specs/<feature>/plan.md`).
+It then creates, replaces, or appends the managed block so that the section points at the most recent plan path when one can be discovered (`specs/**/plan.md`, any depth).
 
 If `context_files` and `context_file` are empty, the command reports nothing to do and exits successfully. Context file paths must stay project-relative; absolute paths, Windows drive paths, backslash separators, and `..` path segments are rejected.
 
@@ -24,4 +24,4 @@ If `context_files` and `context_file` are empty, the command reports nothing to
 - **Bash**: `.specify/extensions/agent-context/scripts/bash/update-agent-context.sh [plan_path]`
 - **PowerShell**: `.specify/extensions/agent-context/scripts/powershell/update-agent-context.ps1 [plan_path]`
 
-When `plan_path` is omitted, the script auto-detects the most recently modified `specs/*/plan.md`.
+When `plan_path` is omitted, the script auto-detects the most recently modified `specs/**/plan.md` (any depth, so scoped layouts like `specs/<scope>/<feature>/plan.md` are found).

extensions/agent-context/scripts/bash/update-agent-context.sh

@@ -12,7 +12,7 @@
 #
 # 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.
+# `specs/**/plan.md` only when feature.json is absent or its plan does not exist yet.
 
 set -euo pipefail
 
@@ -307,14 +307,14 @@ import sys
 from pathlib import Path
 root = Path(sys.argv[1]).resolve()
 specs = root / "specs"
-plans = sorted(
-    specs.glob("*/plan.md"),
+plan = max(
+    specs.glob("**/plan.md"),
     key=lambda p: p.stat().st_mtime,
-    reverse=True,
+    default=None,
 )
-if plans:
+if plan:
     try:
-        print(plans[0].relative_to(root).as_posix())
+        print(plan.relative_to(root).as_posix())
     except ValueError:
         print("")
 else:

extensions/agent-context/scripts/powershell/update-agent-context.ps1

@@ -12,7 +12,7 @@
 #
 # 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.
+# `specs/**/plan.md` only when feature.json is absent or its plan does not exist yet.
 
 [CmdletBinding()]
 param(
@@ -426,9 +426,7 @@ if (-not $PlanPath) {
     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 { $_ } |
+            $candidate = Get-ChildItem -Path $specsDir -Recurse -File -Filter 'plan.md' -ErrorAction SilentlyContinue |
                 Sort-Object LastWriteTime -Descending |
                 Select-Object -First 1
             if ($candidate) {

tests/extensions/test_extension_agent_context.py

@@ -688,6 +688,62 @@ class TestExtensionSelfSeed:
 _MDC_CONTEXT_FILE = ".cursor/rules/specify-rules.mdc"
 
 
+class TestPlanDiscovery:
+    """Mtime fallback must find plans in nested spec layouts (#3024).
+
+    Repos using SPECIFY_FEATURE_DIRECTORY place plans at
+    ``specs/<scope>/<feature>/plan.md``; a one-level ``specs/*/plan.md``
+    glob never matches those.
+    """
+
+    @staticmethod
+    def _make_plans(project: Path) -> Path:
+        # Older flat plan plus a newer nested plan: recursive discovery
+        # must pick the nested one by mtime.
+        flat = project / "specs" / "old-feature" / "plan.md"
+        flat.parent.mkdir(parents=True)
+        flat.write_text("flat plan\n", encoding="utf-8")
+        os.utime(flat, (1_000_000_000, 1_000_000_000))
+        nested = project / "specs" / "scope" / "new-feature" / "plan.md"
+        nested.parent.mkdir(parents=True)
+        nested.write_text("nested plan\n", encoding="utf-8")
+        return nested
+
+    @requires_bash
+    def test_bash_script_finds_nested_plan(self, tmp_path):
+        project = tmp_path / "project"
+        project.mkdir()
+        _install_agent_context_config(
+            project,
+            context_file="AGENTS.md",
+            context_files=["AGENTS.md"],
+        )
+        self._make_plans(project)
+
+        result = _run_bash_agent_context_script(project)
+
+        assert result.returncode == 0, result.stderr + result.stdout
+        content = (project / "AGENTS.md").read_text(encoding="utf-8")
+        assert "specs/scope/new-feature/plan.md" in content
+
+    @pytest.mark.skipif(POWERSHELL is None, reason="PowerShell not available")
+    def test_powershell_script_finds_nested_plan(self, tmp_path):
+        project = tmp_path / "project"
+        project.mkdir()
+        _install_agent_context_config(
+            project,
+            context_file="AGENTS.md",
+            context_files=["AGENTS.md"],
+        )
+        self._make_plans(project)
+
+        result = _run_powershell_agent_context_script(project)
+
+        assert result.returncode == 0, result.stderr + result.stdout
+        content = (project / "AGENTS.md").read_text(encoding="utf-8")
+        assert "specs/scope/new-feature/plan.md" in content
+
+
 class TestMdcFrontmatter:
     """Cursor-style ``.mdc`` targets must carry ``alwaysApply: true`` frontmatter
     so the rule file is auto-loaded; non-``.mdc`` targets must not gain any."""