diff --git a/apps/web-app/.gitignore b/apps/web-app/.gitignore
index 0f94facb..918ec50d 100644
--- a/apps/web-app/.gitignore
+++ b/apps/web-app/.gitignore
@@ -10,6 +10,7 @@ lerna-debug.log*
 node_modules
 dist
 dist-ssr
+coverage
 *.local
 
 # Editor directories and files
diff --git a/plugins/antigravity-awesome-skills-claude/skills/docx-official/ooxml/scripts/unpack.py b/plugins/antigravity-awesome-skills-claude/skills/docx-official/ooxml/scripts/unpack.py
index 96cb94ba..47e55ce4 100755
--- a/plugins/antigravity-awesome-skills-claude/skills/docx-official/ooxml/scripts/unpack.py
+++ b/plugins/antigravity-awesome-skills-claude/skills/docx-official/ooxml/scripts/unpack.py
@@ -2,22 +2,47 @@
 """Unpack and format XML contents of Office files (.docx, .pptx, .xlsx)"""
 
 import random
+import shutil
+import stat
 import sys
 import zipfile
 from pathlib import Path
 
 
+def _is_zip_symlink(member: zipfile.ZipInfo) -> bool:
+    return stat.S_ISLNK(member.external_attr >> 16)
+
+
+def _is_safe_destination(output_root: Path, member_name: str) -> bool:
+    destination = output_root / member_name
+    return destination.resolve().is_relative_to(output_root.resolve())
+
+
+def _extract_member(archive: zipfile.ZipFile, member: zipfile.ZipInfo, output_root: Path):
+    destination = output_root / member.filename
+    if member.is_dir():
+        destination.mkdir(parents=True, exist_ok=True)
+        return
+
+    destination.parent.mkdir(parents=True, exist_ok=True)
+    with archive.open(member, "r") as source, open(destination, "wb") as target:
+        shutil.copyfileobj(source, target)
+
+
 def extract_archive_safely(input_file: str | Path, output_dir: str | Path):
     output_path = Path(output_dir)
     output_path.mkdir(parents=True, exist_ok=True)
+    output_root = output_path.resolve()
 
     with zipfile.ZipFile(input_file) as archive:
         for member in archive.infolist():
-            destination = output_path / member.filename
-            if not destination.resolve().is_relative_to(output_path.resolve()):
+            if _is_zip_symlink(member):
+                raise ValueError(f"Unsafe archive entry: {member.filename}")
+            if not _is_safe_destination(output_root, member.filename):
                 raise ValueError(f"Unsafe archive entry: {member.filename}")
 
-        archive.extractall(output_path)
+        for member in archive.infolist():
+            _extract_member(archive, member, output_path)
 
 
 def pretty_print_xml(output_path: Path):
diff --git a/plugins/antigravity-awesome-skills-claude/skills/pptx-official/ooxml/scripts/unpack.py b/plugins/antigravity-awesome-skills-claude/skills/pptx-official/ooxml/scripts/unpack.py
index 96cb94ba..47e55ce4 100755
--- a/plugins/antigravity-awesome-skills-claude/skills/pptx-official/ooxml/scripts/unpack.py
+++ b/plugins/antigravity-awesome-skills-claude/skills/pptx-official/ooxml/scripts/unpack.py
@@ -2,22 +2,47 @@
 """Unpack and format XML contents of Office files (.docx, .pptx, .xlsx)"""
 
 import random
+import shutil
+import stat
 import sys
 import zipfile
 from pathlib import Path
 
 
+def _is_zip_symlink(member: zipfile.ZipInfo) -> bool:
+    return stat.S_ISLNK(member.external_attr >> 16)
+
+
+def _is_safe_destination(output_root: Path, member_name: str) -> bool:
+    destination = output_root / member_name
+    return destination.resolve().is_relative_to(output_root.resolve())
+
+
+def _extract_member(archive: zipfile.ZipFile, member: zipfile.ZipInfo, output_root: Path):
+    destination = output_root / member.filename
+    if member.is_dir():
+        destination.mkdir(parents=True, exist_ok=True)
+        return
+
+    destination.parent.mkdir(parents=True, exist_ok=True)
+    with archive.open(member, "r") as source, open(destination, "wb") as target:
+        shutil.copyfileobj(source, target)
+
+
 def extract_archive_safely(input_file: str | Path, output_dir: str | Path):
     output_path = Path(output_dir)
     output_path.mkdir(parents=True, exist_ok=True)
+    output_root = output_path.resolve()
 
     with zipfile.ZipFile(input_file) as archive:
         for member in archive.infolist():
-            destination = output_path / member.filename
-            if not destination.resolve().is_relative_to(output_path.resolve()):
+            if _is_zip_symlink(member):
+                raise ValueError(f"Unsafe archive entry: {member.filename}")
+            if not _is_safe_destination(output_root, member.filename):
                 raise ValueError(f"Unsafe archive entry: {member.filename}")
 
-        archive.extractall(output_path)
+        for member in archive.infolist():
+            _extract_member(archive, member, output_path)
 
 
 def pretty_print_xml(output_path: Path):
diff --git a/plugins/antigravity-awesome-skills/skills/docx-official/ooxml/scripts/unpack.py b/plugins/antigravity-awesome-skills/skills/docx-official/ooxml/scripts/unpack.py
index 96cb94ba..47e55ce4 100755
--- a/plugins/antigravity-awesome-skills/skills/docx-official/ooxml/scripts/unpack.py
+++ b/plugins/antigravity-awesome-skills/skills/docx-official/ooxml/scripts/unpack.py
@@ -2,22 +2,47 @@
 """Unpack and format XML contents of Office files (.docx, .pptx, .xlsx)"""
 
 import random
+import shutil
+import stat
 import sys
 import zipfile
 from pathlib import Path
 
 
+def _is_zip_symlink(member: zipfile.ZipInfo) -> bool:
+    return stat.S_ISLNK(member.external_attr >> 16)
+
+
+def _is_safe_destination(output_root: Path, member_name: str) -> bool:
+    destination = output_root / member_name
+    return destination.resolve().is_relative_to(output_root.resolve())
+
+
+def _extract_member(archive: zipfile.ZipFile, member: zipfile.ZipInfo, output_root: Path):
+    destination = output_root / member.filename
+    if member.is_dir():
+        destination.mkdir(parents=True, exist_ok=True)
+        return
+
+    destination.parent.mkdir(parents=True, exist_ok=True)
+    with archive.open(member, "r") as source, open(destination, "wb") as target:
+        shutil.copyfileobj(source, target)
+
+
 def extract_archive_safely(input_file: str | Path, output_dir: str | Path):
     output_path = Path(output_dir)
     output_path.mkdir(parents=True, exist_ok=True)
+    output_root = output_path.resolve()
 
     with zipfile.ZipFile(input_file) as archive:
         for member in archive.infolist():
-            destination = output_path / member.filename
-            if not destination.resolve().is_relative_to(output_path.resolve()):
+            if _is_zip_symlink(member):
+                raise ValueError(f"Unsafe archive entry: {member.filename}")
+            if not _is_safe_destination(output_root, member.filename):
                 raise ValueError(f"Unsafe archive entry: {member.filename}")
 
-        archive.extractall(output_path)
+        for member in archive.infolist():
+            _extract_member(archive, member, output_path)
 
 
 def pretty_print_xml(output_path: Path):
diff --git a/plugins/antigravity-awesome-skills/skills/pptx-official/ooxml/scripts/unpack.py b/plugins/antigravity-awesome-skills/skills/pptx-official/ooxml/scripts/unpack.py
index 96cb94ba..47e55ce4 100755
--- a/plugins/antigravity-awesome-skills/skills/pptx-official/ooxml/scripts/unpack.py
+++ b/plugins/antigravity-awesome-skills/skills/pptx-official/ooxml/scripts/unpack.py
@@ -2,22 +2,47 @@
 """Unpack and format XML contents of Office files (.docx, .pptx, .xlsx)"""
 
 import random
+import shutil
+import stat
 import sys
 import zipfile
 from pathlib import Path
 
 
+def _is_zip_symlink(member: zipfile.ZipInfo) -> bool:
+    return stat.S_ISLNK(member.external_attr >> 16)
+
+
+def _is_safe_destination(output_root: Path, member_name: str) -> bool:
+    destination = output_root / member_name
+    return destination.resolve().is_relative_to(output_root.resolve())
+
+
+def _extract_member(archive: zipfile.ZipFile, member: zipfile.ZipInfo, output_root: Path):
+    destination = output_root / member.filename
+    if member.is_dir():
+        destination.mkdir(parents=True, exist_ok=True)
+        return
+
+    destination.parent.mkdir(parents=True, exist_ok=True)
+    with archive.open(member, "r") as source, open(destination, "wb") as target:
+        shutil.copyfileobj(source, target)
+
+
 def extract_archive_safely(input_file: str | Path, output_dir: str | Path):
     output_path = Path(output_dir)
     output_path.mkdir(parents=True, exist_ok=True)
+    output_root = output_path.resolve()
 
     with zipfile.ZipFile(input_file) as archive:
         for member in archive.infolist():
-            destination = output_path / member.filename
-            if not destination.resolve().is_relative_to(output_path.resolve()):
+            if _is_zip_symlink(member):
+                raise ValueError(f"Unsafe archive entry: {member.filename}")
+            if not _is_safe_destination(output_root, member.filename):
                 raise ValueError(f"Unsafe archive entry: {member.filename}")
 
-        archive.extractall(output_path)
+        for member in archive.infolist():
+            _extract_member(archive, member, output_path)
 
 
 def pretty_print_xml(output_path: Path):
diff --git a/plugins/antigravity-bundle-documents-presentations/skills/docx-official/ooxml/scripts/unpack.py b/plugins/antigravity-bundle-documents-presentations/skills/docx-official/ooxml/scripts/unpack.py
index 96cb94ba..47e55ce4 100755
--- a/plugins/antigravity-bundle-documents-presentations/skills/docx-official/ooxml/scripts/unpack.py
+++ b/plugins/antigravity-bundle-documents-presentations/skills/docx-official/ooxml/scripts/unpack.py
@@ -2,22 +2,47 @@
 """Unpack and format XML contents of Office files (.docx, .pptx, .xlsx)"""
 
 import random
+import shutil
+import stat
 import sys
 import zipfile
 from pathlib import Path
 
 
+def _is_zip_symlink(member: zipfile.ZipInfo) -> bool:
+    return stat.S_ISLNK(member.external_attr >> 16)
+
+
+def _is_safe_destination(output_root: Path, member_name: str) -> bool:
+    destination = output_root / member_name
+    return destination.resolve().is_relative_to(output_root.resolve())
+
+
+def _extract_member(archive: zipfile.ZipFile, member: zipfile.ZipInfo, output_root: Path):
+    destination = output_root / member.filename
+    if member.is_dir():
+        destination.mkdir(parents=True, exist_ok=True)
+        return
+
+    destination.parent.mkdir(parents=True, exist_ok=True)
+    with archive.open(member, "r") as source, open(destination, "wb") as target:
+        shutil.copyfileobj(source, target)
+
+
 def extract_archive_safely(input_file: str | Path, output_dir: str | Path):
     output_path = Path(output_dir)
     output_path.mkdir(parents=True, exist_ok=True)
+    output_root = output_path.resolve()
 
     with zipfile.ZipFile(input_file) as archive:
         for member in archive.infolist():
-            destination = output_path / member.filename
-            if not destination.resolve().is_relative_to(output_path.resolve()):
+            if _is_zip_symlink(member):
+                raise ValueError(f"Unsafe archive entry: {member.filename}")
+            if not _is_safe_destination(output_root, member.filename):
                 raise ValueError(f"Unsafe archive entry: {member.filename}")
 
-        archive.extractall(output_path)
+        for member in archive.infolist():
+            _extract_member(archive, member, output_path)
 
 
 def pretty_print_xml(output_path: Path):
diff --git a/plugins/antigravity-bundle-documents-presentations/skills/pptx-official/ooxml/scripts/unpack.py b/plugins/antigravity-bundle-documents-presentations/skills/pptx-official/ooxml/scripts/unpack.py
index 96cb94ba..47e55ce4 100755
--- a/plugins/antigravity-bundle-documents-presentations/skills/pptx-official/ooxml/scripts/unpack.py
+++ b/plugins/antigravity-bundle-documents-presentations/skills/pptx-official/ooxml/scripts/unpack.py
@@ -2,22 +2,47 @@
 """Unpack and format XML contents of Office files (.docx, .pptx, .xlsx)"""
 
 import random
+import shutil
+import stat
 import sys
 import zipfile
 from pathlib import Path
 
 
+def _is_zip_symlink(member: zipfile.ZipInfo) -> bool:
+    return stat.S_ISLNK(member.external_attr >> 16)
+
+
+def _is_safe_destination(output_root: Path, member_name: str) -> bool:
+    destination = output_root / member_name
+    return destination.resolve().is_relative_to(output_root.resolve())
+
+
+def _extract_member(archive: zipfile.ZipFile, member: zipfile.ZipInfo, output_root: Path):
+    destination = output_root / member.filename
+    if member.is_dir():
+        destination.mkdir(parents=True, exist_ok=True)
+        return
+
+    destination.parent.mkdir(parents=True, exist_ok=True)
+    with archive.open(member, "r") as source, open(destination, "wb") as target:
+        shutil.copyfileobj(source, target)
+
+
 def extract_archive_safely(input_file: str | Path, output_dir: str | Path):
     output_path = Path(output_dir)
     output_path.mkdir(parents=True, exist_ok=True)
+    output_root = output_path.resolve()
 
     with zipfile.ZipFile(input_file) as archive:
         for member in archive.infolist():
-            destination = output_path / member.filename
-            if not destination.resolve().is_relative_to(output_path.resolve()):
+            if _is_zip_symlink(member):
+                raise ValueError(f"Unsafe archive entry: {member.filename}")
+            if not _is_safe_destination(output_root, member.filename):
                 raise ValueError(f"Unsafe archive entry: {member.filename}")
 
-        archive.extractall(output_path)
+        for member in archive.infolist():
+            _extract_member(archive, member, output_path)
 
 
 def pretty_print_xml(output_path: Path):
diff --git a/tools/config/generated-files.json b/tools/config/generated-files.json
index 262adadc..e9d17032 100644
--- a/tools/config/generated-files.json
+++ b/tools/config/generated-files.json
@@ -5,9 +5,13 @@
     "data/skills_index.json",
     "data/catalog.json",
     "data/bundles.json",
+    "data/plugin-compatibility.json",
     "data/aliases.json",
     "apps/web-app/public/sitemap.xml",
-    "apps/web-app/public/skills.json.backup"
+    "apps/web-app/public/skills.json.backup",
+    ".agents/plugins/",
+    ".claude-plugin/",
+    "plugins/"
   ],
   "mixedFiles": [
     "README.md",
diff --git a/tools/lib/workflow-contract.js b/tools/lib/workflow-contract.js
index 71c095a3..b7d776e6 100644
--- a/tools/lib/workflow-contract.js
+++ b/tools/lib/workflow-contract.js
@@ -21,6 +21,21 @@ function normalizeRepoPath(filePath) {
   return String(filePath || "").replace(/\\/g, "/").replace(/^\.\//, "");
 }
 
+function matchesContractEntry(filePath, entry) {
+  const normalizedPath = normalizeRepoPath(filePath);
+  const normalizedEntry = normalizeRepoPath(entry);
+
+  if (!normalizedEntry) {
+    return false;
+  }
+
+  if (normalizedEntry.endsWith("/")) {
+    return normalizedPath.startsWith(normalizedEntry);
+  }
+
+  return normalizedPath === normalizedEntry;
+}
+
 function escapeRegExp(value) {
   return value.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
 }
@@ -57,11 +72,11 @@ function getManagedFiles(contract, options = {}) {
 }
 
 function isDerivedFile(filePath, contract) {
-  return contract.derivedFiles.includes(normalizeRepoPath(filePath));
+  return contract.derivedFiles.some((entry) => matchesContractEntry(filePath, entry));
 }
 
 function isMixedFile(filePath, contract) {
-  return contract.mixedFiles.includes(normalizeRepoPath(filePath));
+  return contract.mixedFiles.some((entry) => matchesContractEntry(filePath, entry));
 }
 
 function isDocLikeFile(filePath) {
@@ -177,5 +192,6 @@ module.exports = {
   isMixedFile,
   loadWorkflowContract,
   normalizeRepoPath,
+  matchesContractEntry,
   requiresReferencesValidation,
 };
diff --git a/tools/scripts/tests/automation_workflows.test.js b/tools/scripts/tests/automation_workflows.test.js
index 12a7688c..d44eddc1 100644
--- a/tools/scripts/tests/automation_workflows.test.js
+++ b/tools/scripts/tests/automation_workflows.test.js
@@ -60,6 +60,10 @@ assert.strictEqual(
 for (const filePath of [
   "apps/web-app/public/sitemap.xml",
   "apps/web-app/public/skills.json.backup",
+  "data/plugin-compatibility.json",
+  ".agents/plugins/",
+  ".claude-plugin/",
+  "plugins/",
 ]) {
   assert.ok(
     generatedFiles.derivedFiles.includes(filePath),
@@ -67,6 +71,13 @@ for (const filePath of [
   );
 }
 
+const webAppGitignore = readText("apps/web-app/.gitignore");
+assert.match(
+  webAppGitignore,
+  /^coverage$/m,
+  "web-app coverage output should be ignored so maintainer sync jobs stay clean",
+);
+
 for (const filePath of [
   "README.md",
   "package.json",
diff --git a/tools/scripts/tests/workflow_contracts.test.js b/tools/scripts/tests/workflow_contracts.test.js
index 36bb08cd..0318e46d 100644
--- a/tools/scripts/tests/workflow_contracts.test.js
+++ b/tools/scripts/tests/workflow_contracts.test.js
@@ -16,7 +16,11 @@ const contract = {
     "data/skills_index.json",
     "data/catalog.json",
     "data/bundles.json",
+    "data/plugin-compatibility.json",
     "data/aliases.json",
+    ".agents/plugins/",
+    ".claude-plugin/",
+    "plugins/",
   ],
   mixedFiles: ["README.md"],
   releaseManagedFiles: ["CHANGELOG.md", "package.json", "package-lock.json", "README.md"],
@@ -45,6 +49,20 @@ assert.deepStrictEqual(
   getDirectDerivedChanges(["skills/example/SKILL.md", "data/catalog.json"], contract),
   ["data/catalog.json"],
 );
+assert.deepStrictEqual(
+  getDirectDerivedChanges(
+    [
+      "plugins/antigravity-awesome-skills/skills/docx-official/ooxml/scripts/unpack.py",
+      ".agents/plugins/marketplace.json",
+      "skills/example/SKILL.md",
+    ],
+    contract,
+  ),
+  [
+    "plugins/antigravity-awesome-skills/skills/docx-official/ooxml/scripts/unpack.py",
+    ".agents/plugins/marketplace.json",
+  ],
+);
 
 const changelog = [
   "## [7.7.0] - 2026-03-13 - \"Merge Friction Reduction\"",