diff --git a/extensions/agent-context/commands/speckit.agent-context.update.md b/extensions/agent-context/commands/speckit.agent-context.update.md
index 02f1706926..c45a8893f1 100644
--- a/extensions/agent-context/commands/speckit.agent-context.update.md
+++ b/extensions/agent-context/commands/speckit.agent-context.update.md
@@ -14,7 +14,7 @@ The script reads the agent-context extension config at
 - `context_file` — the path of the coding agent context file to manage.
 - `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`).
 
 If `context_file` is empty or the file cannot be located, the command reports nothing to do and exits successfully.
 
@@ -23,4 +23,4 @@ If `context_file` is empty or the file cannot be located, the command reports no
 - **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 `plan.md` anywhere under `specs/`.
diff --git a/extensions/agent-context/scripts/bash/update-agent-context.sh b/extensions/agent-context/scripts/bash/update-agent-context.sh
index 42ce44df9a..3ef4326703 100755
--- a/extensions/agent-context/scripts/bash/update-agent-context.sh
+++ b/extensions/agent-context/scripts/bash/update-agent-context.sh
@@ -11,7 +11,7 @@
 # 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
+# `specs/**/plan.md` if any exist, otherwise emits the section without a
 # concrete plan path.
 
 set -euo pipefail
@@ -122,7 +122,7 @@ 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).
+  # Pick the most recently modified plan.md anywhere under specs/.
   # Use find + sort by modification time to avoid ls/head fragility with
   # spaces in paths or SIGPIPE from pipefail.
   _plan_abs="$("$_python" - "$PROJECT_ROOT" <<'PY'
@@ -130,7 +130,7 @@ import sys, os
 from pathlib import Path
 specs = Path(sys.argv[1]) / "specs"
 plans = sorted(
-    specs.glob("*/plan.md"),
+    specs.glob("**/plan.md"),
     key=lambda p: p.stat().st_mtime,
     reverse=True,
 )
diff --git a/extensions/agent-context/scripts/powershell/update-agent-context.ps1 b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
index dad309c03a..df22990f95 100644
--- a/extensions/agent-context/scripts/powershell/update-agent-context.ps1
+++ b/extensions/agent-context/scripts/powershell/update-agent-context.ps1
@@ -166,13 +166,12 @@ if ($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.
+    # Discover plan.md anywhere under specs/, picking the most recently modified file.
+    # 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 } |
+        $candidate = Get-ChildItem -Path $specsDir -Recurse -Filter 'plan.md' -File -ErrorAction SilentlyContinue |
             Where-Object { $_ } |
             Sort-Object LastWriteTime -Descending |
             Select-Object -First 1
diff --git a/tests/extensions/test_extension_agent_context.py b/tests/extensions/test_extension_agent_context.py
index 61ecab91af..a0e78d5d19 100644
--- a/tests/extensions/test_extension_agent_context.py
+++ b/tests/extensions/test_extension_agent_context.py
@@ -3,8 +3,12 @@
 from __future__ import annotations
 
 import json
+import os
+import shutil
+import subprocess
 from pathlib import Path
 
+import pytest
 import yaml
 
 from specify_cli import (
@@ -15,10 +19,13 @@
 )
 from specify_cli.integrations.base import IntegrationBase
 from specify_cli.integrations.claude import ClaudeIntegration
+from tests.conftest import requires_bash
 
 
 PROJECT_ROOT = Path(__file__).resolve().parent.parent.parent
 EXT_DIR = PROJECT_ROOT / "extensions" / "agent-context"
+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 _write_ext_config(project_root: Path, **overrides: object) -> None:
@@ -36,6 +43,22 @@ def _write_ext_config(project_root: Path, **overrides: object) -> None:
     _save_agent_context_config(project_root, cfg)
 
 
+def _prepare_agent_context_project(project_root: Path) -> None:
+    (project_root / ".specify" / "extensions" / "agent-context").mkdir(
+        parents=True,
+        exist_ok=True,
+    )
+    _write_ext_config(project_root, context_file="CLAUDE.md")
+
+
+def _clean_env() -> dict[str, str]:
+    env = os.environ.copy()
+    for key in list(env):
+        if key.startswith("SPECIFY_"):
+            env.pop(key)
+    return env
+
+
 # ── Bundled extension layout ─────────────────────────────────────────────────
 
 
@@ -426,6 +449,53 @@ def test_marker_resolution_with_corrupt_yaml(self, tmp_path):
         assert start == IntegrationBase.CONTEXT_MARKER_START
         assert end == IntegrationBase.CONTEXT_MARKER_END
 
+
+# ── Script discovery for nested plan paths ──────────────────────────────────
+
+
+class TestNestedPlanDiscovery:
+    @requires_bash
+    def test_bash_script_resolves_nested_plan(self, tmp_path):
+        _prepare_agent_context_project(tmp_path)
+        nested_plan = tmp_path / "specs" / "scope" / "feature" / "plan.md"
+        nested_plan.parent.mkdir(parents=True, exist_ok=True)
+        nested_plan.write_text("# plan\n", encoding="utf-8")
+        script = EXT_DIR / "scripts" / "bash" / "update-agent-context.sh"
+        result = subprocess.run(
+            ["bash", str(script)],
+            cwd=tmp_path,
+            capture_output=True,
+            text=True,
+            check=False,
+            env=_clean_env(),
+        )
+        assert result.returncode == 0, result.stderr
+        text = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+        assert "specs/scope/feature/plan.md" in text
+
+    @pytest.mark.skipif(
+        not (HAS_PWSH or _WINDOWS_POWERSHELL),
+        reason="no PowerShell available",
+    )
+    def test_powershell_script_resolves_nested_plan(self, tmp_path):
+        _prepare_agent_context_project(tmp_path)
+        nested_plan = tmp_path / "specs" / "scope" / "feature" / "plan.md"
+        nested_plan.parent.mkdir(parents=True, exist_ok=True)
+        nested_plan.write_text("# plan\n", encoding="utf-8")
+        script = EXT_DIR / "scripts" / "powershell" / "update-agent-context.ps1"
+        exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
+        result = subprocess.run(
+            [exe, "-NoProfile", "-File", str(script)],
+            cwd=tmp_path,
+            capture_output=True,
+            text=True,
+            check=False,
+            env=_clean_env(),
+        )
+        assert result.returncode == 0, result.stderr
+        text = (tmp_path / "CLAUDE.md").read_text(encoding="utf-8")
+        assert "specs/scope/feature/plan.md" in text
+
     def test_upsert_with_corrupt_config_uses_defaults(self, tmp_path):
         """upsert_context_section still works when config YAML is corrupt."""
         cfg_path = (