diff --git a/engine/src/flutter/build/archives/BUILD.gn b/engine/src/flutter/build/archives/BUILD.gn
index f91ca65bec7..e09d101afca 100644
--- a/engine/src/flutter/build/archives/BUILD.gn
+++ b/engine/src/flutter/build/archives/BUILD.gn
@@ -5,6 +5,21 @@
 import("//flutter/build/zip_bundle.gni")
 import("//flutter/common/config.gni")
 
+generated_file("artifacts_entitlement_config") {
+  outputs = [ "$target_gen_dir/entitlements.txt" ]
+
+  data_keys = [ "entitlement_file_path" ]
+
+  deps = [ "//flutter/lib/snapshot:generate_snapshot_bin" ]
+  if (flutter_runtime_mode == "debug") {
+    deps += [
+      "//flutter/impeller/compiler:impellerc",
+      "//flutter/impeller/tessellator:tessellator_shared",
+      "//flutter/shell/testing:testing",
+    ]
+  }
+}
+
 if (build_engine_artifacts) {
   zip_bundle("artifacts") {
     deps = [
@@ -69,6 +84,15 @@ if (build_engine_artifacts) {
         destination = "libtessellator$dll"
       },
     ]
+    if (host_os == "mac") {
+      deps += [ ":artifacts_entitlement_config" ]
+      files += [
+        {
+          source = "$target_gen_dir/entitlements.txt"
+          destination = "entitlements.txt"
+        },
+      ]
+    }
   }
 }
 
diff --git a/engine/src/flutter/impeller/compiler/BUILD.gn b/engine/src/flutter/impeller/compiler/BUILD.gn
index 54f2b8560b7..9bd3ffda346 100644
--- a/engine/src/flutter/impeller/compiler/BUILD.gn
+++ b/engine/src/flutter/impeller/compiler/BUILD.gn
@@ -89,6 +89,10 @@ impeller_component("impellerc") {
   sources = [ "impellerc_main.cc" ]
 
   deps = [ ":compiler_lib" ]
+
+  metadata = {
+    entitlement_file_path = [ "impellerc" ]
+  }
 }
 
 group("compiler") {
diff --git a/engine/src/flutter/impeller/tessellator/BUILD.gn b/engine/src/flutter/impeller/tessellator/BUILD.gn
index a3d1b3ef1c4..d3915f99966 100644
--- a/engine/src/flutter/impeller/tessellator/BUILD.gn
+++ b/engine/src/flutter/impeller/tessellator/BUILD.gn
@@ -34,6 +34,10 @@ impeller_component("tessellator_shared") {
     "../geometry",
     "//third_party/libtess2",
   ]
+
+  metadata = {
+    entitlement_file_path = [ "libtessellator.dylib" ]
+  }
 }
 
 impeller_component("tessellator_unittests") {
diff --git a/engine/src/flutter/lib/snapshot/BUILD.gn b/engine/src/flutter/lib/snapshot/BUILD.gn
index 01cbbc12277..f78ff9f98d0 100644
--- a/engine/src/flutter/lib/snapshot/BUILD.gn
+++ b/engine/src/flutter/lib/snapshot/BUILD.gn
@@ -67,6 +67,10 @@ compiled_action("generate_snapshot_bin") {
   }
 
   args += [ rebase_path(platform_kernel) ]
+
+  metadata = {
+    entitlement_file_path = [ "gen_snapshot" ]
+  }
 }
 
 # Generates an assembly file defining a given symbol with the bytes from a
diff --git a/engine/src/flutter/shell/testing/BUILD.gn b/engine/src/flutter/shell/testing/BUILD.gn
index 247b168bae9..ec6400ce076 100644
--- a/engine/src/flutter/shell/testing/BUILD.gn
+++ b/engine/src/flutter/shell/testing/BUILD.gn
@@ -35,4 +35,8 @@ executable("testing") {
     "//third_party/dart/runtime/bin:dart_io_api",
     "//third_party/skia",
   ]
+
+  metadata = {
+    entitlement_file_path = [ "flutter_tester" ]
+  }
 }