diff --git a/examples/bundles/business-analyst/bundle.yml b/examples/bundles/business-analyst/bundle.yml
index b03875a22e..90d35ce87d 100644
--- a/examples/bundles/business-analyst/bundle.yml
+++ b/examples/bundles/business-analyst/bundle.yml
@@ -17,7 +17,7 @@ requires:
 provides:
   extensions:
     - id: "agent-context"
-      version: "1.0.0"
+      version: "1.1.0"
   presets:
     - id: "requirements-elicitation"
       version: "1.0.0"
diff --git a/examples/bundles/developer/bundle.yml b/examples/bundles/developer/bundle.yml
index 3a365534e5..3f4dce5465 100644
--- a/examples/bundles/developer/bundle.yml
+++ b/examples/bundles/developer/bundle.yml
@@ -17,7 +17,7 @@ requires:
 provides:
   extensions:
     - id: "agent-context"
-      version: "1.0.0"
+      version: "1.1.0"
   presets:
     - id: "implementation-planning"
       version: "1.0.0"
diff --git a/examples/bundles/product-manager/bundle.yml b/examples/bundles/product-manager/bundle.yml
index 9abba40bd4..c5f96ab186 100644
--- a/examples/bundles/product-manager/bundle.yml
+++ b/examples/bundles/product-manager/bundle.yml
@@ -19,7 +19,7 @@ requires:
 provides:
   extensions:
     - id: "agent-context"
-      version: "1.0.0"
+      version: "1.1.0"
   presets:
     - id: "product-discovery"
       version: "1.0.0"
diff --git a/examples/bundles/security-researcher/bundle.yml b/examples/bundles/security-researcher/bundle.yml
index d0b289e872..e017071e94 100644
--- a/examples/bundles/security-researcher/bundle.yml
+++ b/examples/bundles/security-researcher/bundle.yml
@@ -17,7 +17,7 @@ requires:
 provides:
   extensions:
     - id: "agent-context"
-      version: "1.0.0"
+      version: "1.1.0"
   presets:
     - id: "security-compliance"
       version: "1.0.0"
diff --git a/extensions/agent-context/extension.yml b/extensions/agent-context/extension.yml
index 191069e32c..2846b4d9a6 100644
--- a/extensions/agent-context/extension.yml
+++ b/extensions/agent-context/extension.yml
@@ -3,7 +3,7 @@ schema_version: "1.0"
 extension:
   id: agent-context
   name: "Coding Agent Context"
-  version: "1.0.0"
+  version: "1.1.0"
   description: "Manages coding agent context/instruction files (e.g., CLAUDE.md, copilot-instructions.md) with project-specific plan references and configurable markers"
   author: spec-kit-core
   repository: https://github.com/github/spec-kit
diff --git a/extensions/assess/extension.yml b/extensions/assess/extension.yml
index 9161b268fb..42b281b8ee 100644
--- a/extensions/assess/extension.yml
+++ b/extensions/assess/extension.yml
@@ -3,7 +3,7 @@ schema_version: "1.0"
 extension:
   id: assess
   name: "Idea Assessment Pipeline"
-  version: "1.0.0"
+  version: "1.0.1"
   description: "Assess an idea before Spec-Driven Development via intake, research, define, shape, and decide. A go verdict hands off to /speckit.specify; a kill closes it. Lives under .specify/assessments/<slug>/"
   category: "process"
   effect: "read-write"
diff --git a/extensions/catalog.json b/extensions/catalog.json
index d05c48e0e5..af0aae7701 100644
--- a/extensions/catalog.json
+++ b/extensions/catalog.json
@@ -1,12 +1,12 @@
 {
   "schema_version": "1.0",
-  "updated_at": "2026-07-17T00:00:00Z",
+  "updated_at": "2026-08-27T00:00:00Z",
   "catalog_url": "https://raw.githubusercontent.com/github/spec-kit/main/extensions/catalog.json",
   "extensions": {
     "agent-context": {
       "name": "Coding Agent Context",
       "id": "agent-context",
-      "version": "1.0.0",
+      "version": "1.1.0",
       "description": "Manages coding agent context/instruction files (e.g., CLAUDE.md, copilot-instructions.md) with project-specific plan references and configurable markers",
       "author": "spec-kit-core",
       "repository": "https://github.com/github/spec-kit",
@@ -20,7 +20,7 @@
     "assess": {
       "name": "Idea Assessment Pipeline",
       "id": "assess",
-      "version": "1.0.0",
+      "version": "1.0.1",
       "description": "Assess an idea before Spec-Driven Development via intake, research, define, shape, and decide. A go verdict hands off to /speckit.specify; a kill closes it. Lives under .specify/assessments/<slug>/",
       "author": "spec-kit-core",
       "repository": "https://github.com/github/spec-kit",
@@ -51,7 +51,7 @@
     "git": {
       "name": "Git Branching Workflow",
       "id": "git",
-      "version": "1.0.0",
+      "version": "1.1.0",
       "description": "Feature branch creation, numbering (sequential/timestamp), validation, and Git remote detection",
       "author": "spec-kit-core",
       "repository": "https://github.com/github/spec-kit",
diff --git a/extensions/git/extension.yml b/extensions/git/extension.yml
index c92322d8b1..84e2dc35a5 100644
--- a/extensions/git/extension.yml
+++ b/extensions/git/extension.yml
@@ -3,7 +3,7 @@ schema_version: "1.0"
 extension:
   id: git
   name: "Git Branching Workflow"
-  version: "1.0.0"
+  version: "1.1.0"
   description: "Feature branch creation, numbering (sequential/timestamp), templating, validation, and Git remote detection"
   author: spec-kit-core
   repository: https://github.com/github/spec-kit
diff --git a/tests/bundler_helpers.py b/tests/bundler_helpers.py
index 0ebaf2f1c7..2df11e03df 100644
--- a/tests/bundler_helpers.py
+++ b/tests/bundler_helpers.py
@@ -43,6 +43,24 @@ def valid_manifest_dict(**overrides) -> dict:
     return data
 
 
+def bundled_extension_version(extension_id: str) -> str:
+    """Version declared by the bundled extension the primitives will install.
+
+    Resolved through the same lookup ``BundleExtensionPrimitive`` uses, so
+    fixtures that pin a real bundled extension stay valid across legitimate
+    extension version bumps (#4345) instead of hardcoding a literal that
+    drifts out of sync and trips the exact-pin enforcement.
+    """
+    from specify_cli._assets import _locate_bundled_extension
+
+    bundled_dir = _locate_bundled_extension(extension_id)
+    assert bundled_dir is not None, f"bundled extension '{extension_id}' not found"
+    manifest = yaml.safe_load(
+        (bundled_dir / "extension.yml").read_text(encoding="utf-8")
+    )
+    return manifest["extension"]["version"]
+
+
 def write_manifest(directory: Path, data: dict | None = None) -> Path:
     directory.mkdir(parents=True, exist_ok=True)
     manifest_path = directory / "bundle.yml"
diff --git a/tests/contract/test_bundled_extension_update_delivery.py b/tests/contract/test_bundled_extension_update_delivery.py
new file mode 100644
index 0000000000..f85e745829
--- /dev/null
+++ b/tests/contract/test_bundled_extension_update_delivery.py
@@ -0,0 +1,157 @@
+"""Contract tests: previously stale bundled installs are now offered an update.
+
+Every bundled extension shipped at 1.0.0 from its creation while its content
+kept changing, so installed copies were reported "Up to date" forever
+(#4345). The version bumps in extensions/*/extension.yml and the synced
+extensions/catalog.json are what finally make `specify extension update`
+offer those installs a newer version, and the local-package route installs
+it from the copy bundled with the running spec-kit.
+
+Unit tests cover that route with synthetic extensions and versions, and the
+version contract only checks catalog/manifest equality. These tests close
+the gap with the real data: install each bundled extension's real source
+at the pre-bump 1.0.0, run `extension update` against the real catalog
+entry and the real bundled copy, and assert it reaches the catalog version.
+"""
+
+from __future__ import annotations
+
+import json
+import shutil
+from pathlib import Path
+from unittest.mock import patch
+
+import pytest
+import yaml
+from packaging.version import Version
+from typer.testing import CliRunner
+
+REPO_ROOT = Path(__file__).parents[2]
+EXTENSIONS_ROOT = REPO_ROOT / "extensions"
+PRE_BUMP_VERSION = "1.0.0"
+# Bundled extensions whose content had drifted while still declaring 1.0.0
+# when #4345 was filed. Their catalog version must stay above PRE_BUMP_VERSION
+# so a copy installed before the fix is actually offered an update; a version
+# that is not bumped past it here is a regression, not a skip.
+DRIFTED_BEFORE_BUMP = frozenset({"agent-context", "assess", "git"})
+
+
+def _catalog_entries() -> dict[str, dict]:
+    catalog = json.loads((EXTENSIONS_ROOT / "catalog.json").read_text(encoding="utf-8"))
+    return catalog["extensions"]
+
+
+def _bundled_ids() -> list[str]:
+    return sorted(
+        ext_id
+        for ext_id, entry in _catalog_entries().items()
+        if entry.get("bundled")
+        and not entry.get("download_url")
+        and (EXTENSIONS_ROOT / ext_id / "extension.yml").is_file()
+    )
+
+
+def _make_project(tmp_path: Path) -> Path:
+    project_dir = tmp_path / "project"
+    project_dir.mkdir()
+    (project_dir / ".specify").mkdir()
+    (project_dir / ".claude" / "skills").mkdir(parents=True)
+    return project_dir
+
+
+def _stale_copy(tmp_path: Path, ext_id: str, version: str) -> Path:
+    """The real bundled source with only its manifest version rewritten."""
+    source = tmp_path / "stale" / ext_id
+    shutil.copytree(EXTENSIONS_ROOT / ext_id, source)
+    manifest_path = source / "extension.yml"
+    data = yaml.safe_load(manifest_path.read_text(encoding="utf-8"))
+    data["extension"]["version"] = version
+    manifest_path.write_text(yaml.safe_dump(data, sort_keys=False), encoding="utf-8")
+    return source
+
+
+def _run_update(project_dir: Path, ext_id: str):
+    from specify_cli import app
+    from specify_cli.extensions import ExtensionCatalog
+
+    catalog_info = dict(_catalog_entries()[ext_id])
+    catalog_info.setdefault("_install_allowed", True)
+    # Real catalog entry and real bundled copy; only the network fetch of the
+    # catalog is replaced, and downloading must never be attempted for a
+    # bundled extension.
+    with patch.object(Path, "cwd", return_value=project_dir), \
+         patch.object(ExtensionCatalog, "get_extension_info", return_value=catalog_info), \
+         patch.object(
+             ExtensionCatalog,
+             "download_extension",
+             side_effect=AssertionError("bundled update must not download"),
+         ):
+        return CliRunner().invoke(
+            app, ["extension", "update", ext_id], input="y\n", catch_exceptions=True
+        )
+
+
+def test_drifted_extensions_are_covered():
+    """The parametrized tests below draw their cases from the live catalog, so
+    an extension that lost its ``bundled`` flag, its catalog entry, or its
+    in-repo manifest would silently drop out of them and the
+    ``DRIFTED_BEFORE_BUMP`` guard inside would never run for it. Pin the
+    coverage itself: every extension known to have drifted must still be a
+    bundled, in-repo catalog entry. De-bundling one of them is a deliberate
+    decision that should update this set, not a silent loss of coverage."""
+    covered = set(_bundled_ids())
+    missing = DRIFTED_BEFORE_BUMP - covered
+    assert not missing, (
+        f"{sorted(missing)} drifted before #4345 but are no longer bundled, in-repo "
+        f"catalog entries, so the update-delivery tests no longer cover them"
+    )
+
+
+@pytest.mark.parametrize("ext_id", _bundled_ids())
+def test_stale_bundled_install_is_updated_to_catalog_version(tmp_path: Path, ext_id: str):
+    from specify_cli._assets import get_speckit_version
+    from specify_cli.extensions import ExtensionManager
+
+    catalog_version = Version(_catalog_entries()[ext_id]["version"])
+    if catalog_version <= Version(PRE_BUMP_VERSION):
+        assert ext_id not in DRIFTED_BEFORE_BUMP, (
+            f"'{ext_id}' drifted at {PRE_BUMP_VERSION} before #4345 but the catalog still "
+            f"advertises {catalog_version}; installs made before the fix would never be "
+            f"offered the shipped changes"
+        )
+        pytest.skip(f"'{ext_id}' has not been bumped past {PRE_BUMP_VERSION}; nothing to deliver")
+
+    project_dir = _make_project(tmp_path)
+    stale_source = _stale_copy(tmp_path, ext_id, PRE_BUMP_VERSION)
+    manager = ExtensionManager(project_dir)
+    manager.install_from_directory(stale_source, get_speckit_version())
+    assert manager.registry.get(ext_id)["version"] == PRE_BUMP_VERSION
+
+    result = _run_update(project_dir, ext_id)
+
+    flat = " ".join(result.output.split())
+    assert result.exit_code == 0, result.output
+    assert f"Updated to v{catalog_version}" in flat, flat
+    assert "Up to date" not in flat, flat
+    assert ExtensionManager(project_dir).registry.get(ext_id)["version"] == str(catalog_version)
+
+
+@pytest.mark.parametrize("ext_id", _bundled_ids())
+def test_current_bundled_install_is_up_to_date(tmp_path: Path, ext_id: str):
+    """The bumped catalog must not re-offer an update to an install that
+    already carries the bundled version, or every fresh install would loop."""
+    from specify_cli._assets import get_speckit_version
+    from specify_cli.extensions import ExtensionManager
+
+    catalog_version = _catalog_entries()[ext_id]["version"]
+    project_dir = _make_project(tmp_path)
+    ExtensionManager(project_dir).install_from_directory(
+        EXTENSIONS_ROOT / ext_id, get_speckit_version()
+    )
+
+    result = _run_update(project_dir, ext_id)
+
+    flat = " ".join(result.output.split())
+    assert result.exit_code == 0, result.output
+    assert f"Up to date (v{catalog_version})" in flat, flat
+    assert ExtensionManager(project_dir).registry.get(ext_id)["version"] == catalog_version
diff --git a/tests/contract/test_bundled_extension_versions.py b/tests/contract/test_bundled_extension_versions.py
index 2d7f0c6c0e..f86f0afc72 100644
--- a/tests/contract/test_bundled_extension_versions.py
+++ b/tests/contract/test_bundled_extension_versions.py
@@ -25,6 +25,7 @@
 
 REPO_ROOT = Path(__file__).parents[2]
 EXTENSIONS_ROOT = REPO_ROOT / "extensions"
+EXAMPLE_BUNDLES_ROOT = REPO_ROOT / "examples" / "bundles"
 
 
 def _catalog_entries() -> dict[str, dict]:
@@ -81,3 +82,39 @@ def test_catalog_version_is_valid_pep440(ext_id: str):
             f"extensions/catalog.json entry '{ext_id}' version {version!r} is not a valid "
             f"PEP 440 version ({exc}); `extension update` would skip it"
         )
+
+
+def _example_bundle_extension_pins() -> list[tuple[str, str, str]]:
+    """(bundle name, extension id, pinned version) for every example bundle."""
+    pins = []
+    for manifest_path in sorted(EXAMPLE_BUNDLES_ROOT.glob("*/bundle.yml")):
+        data = yaml.safe_load(manifest_path.read_text(encoding="utf-8"))
+        for entry in (data.get("provides") or {}).get("extensions") or []:
+            pins.append((manifest_path.parent.name, entry["id"], str(entry.get("version"))))
+    return pins
+
+
+def test_example_bundles_pin_extensions():
+    assert _example_bundle_extension_pins(), "expected at least one extension pin in examples/bundles"
+
+
+@pytest.mark.parametrize(
+    "bundle_name,ext_id,pinned",
+    _example_bundle_extension_pins(),
+    ids=lambda v: v if isinstance(v, str) else str(v),
+)
+def test_example_bundle_pins_match_bundled_manifest(bundle_name: str, ext_id: str, pinned: str):
+    """``BundleExtensionPrimitive`` refuses to install when the resolved
+    extension version differs from the bundle's pin, so an example bundle that
+    still pins a bundled extension's previous version fails for every user who
+    installs it. Test fixtures derive their pins from the bundled manifest and
+    therefore cannot catch this; the shipped examples must be checked directly."""
+    manifest_path = EXTENSIONS_ROOT / ext_id / "extension.yml"
+    if not manifest_path.is_file():
+        pytest.skip(f"'{ext_id}' is not a bundled extension; pin resolves via the catalog at install time")
+    manifest_version = _manifest_version(ext_id)
+    assert Version(pinned) == Version(manifest_version), (
+        f"examples/bundles/{bundle_name}/bundle.yml pins '{ext_id}' to {pinned} but "
+        f"{manifest_path.relative_to(REPO_ROOT)} declares {manifest_version}; the bundler "
+        f"enforces exact pins, so installing this example would fail"
+    )
diff --git a/tests/extensions/git/test_git_extension.py b/tests/extensions/git/test_git_extension.py
index f6be51caf6..5bc25b9332 100644
--- a/tests/extensions/git/test_git_extension.py
+++ b/tests/extensions/git/test_git_extension.py
@@ -145,7 +145,7 @@ def test_manifest_validates(self):
 
         m = ExtensionManifest(EXT_DIR / "extension.yml")
         assert m.id == "git"
-        assert m.version == "1.0.0"
+        assert m.version == "1.1.0"
 
     def test_manifest_commands(self):
         """Manifest declares expected commands."""
diff --git a/tests/integration/test_bundler_init_install.py b/tests/integration/test_bundler_init_install.py
index a13def5ff8..291c67871f 100644
--- a/tests/integration/test_bundler_init_install.py
+++ b/tests/integration/test_bundler_init_install.py
@@ -18,7 +18,7 @@
 from specify_cli.bundler.models.manifest import BundleManifest
 from specify_cli.commands.bundle import _resolve_init_integration
 from specify_cli.bundler.services.packager import build_bundle
-from tests.bundler_helpers import valid_manifest_dict
+from tests.bundler_helpers import bundled_extension_version, valid_manifest_dict
 
 runner = CliRunner()
 
@@ -75,7 +75,14 @@ def _build_mini(tmp_path: Path) -> Path:
                     "license": "MIT",
                 },
                 "requires": {"speckit_version": ">=0.1.0"},
-                "provides": {"extensions": [{"id": "agent-context", "version": "1.0.0"}]},
+                "provides": {
+                    "extensions": [
+                        {
+                            "id": "agent-context",
+                            "version": bundled_extension_version("agent-context"),
+                        }
+                    ]
+                },
             }
         ),
         encoding="utf-8",
diff --git a/tests/integration/test_bundler_local_install.py b/tests/integration/test_bundler_local_install.py
index 7655543ebb..5760bfb4e1 100644
--- a/tests/integration/test_bundler_local_install.py
+++ b/tests/integration/test_bundler_local_install.py
@@ -18,7 +18,13 @@
 from specify_cli import app
 from specify_cli.bundler import BundlerError
 from specify_cli.commands.bundle import _local_manifest_source
-from tests.bundler_helpers import FakeInstaller, make_project, valid_manifest_dict, write_manifest
+from tests.bundler_helpers import (
+    FakeInstaller,
+    bundled_extension_version,
+    make_project,
+    valid_manifest_dict,
+    write_manifest,
+)
 
 
 def test_local_source_none_for_non_path():
@@ -116,7 +122,12 @@ def test_install_bundled_extension_from_zip_offline(tmp_path: Path):
                 },
                 "requires": {"speckit_version": ">=0.1.0"},
                 "provides": {
-                    "extensions": [{"id": "agent-context", "version": "1.0.0"}]
+                    "extensions": [
+                        {
+                            "id": "agent-context",
+                            "version": bundled_extension_version("agent-context"),
+                        }
+                    ]
                 },
             }
         ),