diff --git a/elm_deps_sync.py b/elm_deps_sync.py
index 95bffc8..6d69244 100755
--- a/elm_deps_sync.py
+++ b/elm_deps_sync.py
@@ -16,7 +16,7 @@ def sync_versions(top_level_file, spec_file, quiet=False, dry=False, note_test_d
         top_level = json.load(f)
 
     with open(spec_file) as f:
-        spec = json.load(f)
+        spec = json.load(f, object_pairs_hook=OrderedDict)
 
     messages = []
 
diff --git a/tests/test_elm_deps_sync.py b/tests/test_elm_deps_sync.py
index 08b3d99..0204d07 100644
--- a/tests/test_elm_deps_sync.py
+++ b/tests/test_elm_deps_sync.py
@@ -2,29 +2,55 @@
 import json
 
 import pytest
+from hypothesis import given
+import hypothesis.strategies as st
 
 import elm_deps_sync
 
 
-def test_spec_order_is_preserved(tmpdir):
+package_skeleton = {
+    "version": "1.0.0",
+    "summary": "test elm deps sync",
+    "repository": "https://github.com/NoRedInk/elm-ops-tooling",
+    "license": "BSD-3",
+    "source-directories": ".",
+    "exposed-modules": [],
+    "native-modules": True,
+    "dependencies": {},
+    "elm-version": "0.17.0 <= v <= 0.17.0",
+}
+
+top_level_deps = [
+    ('NoRedInk/top-1', '1.0.0 <= v <= 1.0.0'),
+    ('NoRedInk/top-2', '1.0.0 <= v <= 1.0.0'),
+    ('NoRedInk/top-3', '1.0.0 <= v <= 1.0.0'),
+]
+
+spec_deps = [
+    ('NoRedInk/top-1', '1.0.0 <= v <= 1.0.0'),
+    ('NoRedInk/top-2', '1.0.0 <= v <= 1.0.0'),
+    ('NoRedInk/spec-1', '1.0.0 <= v <= 1.0.0'),
+    ('NoRedInk/spec-2', '1.0.0 <= v <= 1.0.0'),
+]
+
+
+@given(top_level_keys=st.permutations(package_skeleton.keys()),
+       top_level_deps=st.permutations(top_level_deps),
+       spec_keys=st.permutations(package_skeleton.keys()),
+       spec_deps=st.permutations(spec_deps))
+def test_spec_order_is_preserved(
+        tmpdir,
+        top_level_keys,
+        top_level_deps,
+        spec_keys,
+        spec_deps):
     top_level_file = tmpdir.join('elm-package.json')
     spec_file = tmpdir.join('spec-elm-package.json')
 
-    top_level = {
-        'dependencies': OrderedDict([
-            ('NoRedInk/top-3', '1.0.0 <= v <= 1.0.0'),
-            ('NoRedInk/top-1', '1.0.0 <= v <= 1.0.0'),
-            ('NoRedInk/top-2', '1.0.0 <= v <= 1.0.0'),
-        ])
-    }
+    top_level = _make_package(top_level_keys, top_level_deps)
     top_level_file.write(json.dumps(top_level))
 
-    spec = {
-        'dependencies': OrderedDict([
-            ('NoRedInk/top-2', '1.0.0 <= v <= 1.0.0'),
-            ('NoRedInk/top-1', '1.0.0 <= v <= 1.0.0'),
-        ])
-    }
+    spec = _make_package(spec_keys, spec_deps)
     spec_file.write(json.dumps(spec))
 
     elm_deps_sync.sync_versions(
@@ -35,4 +61,12 @@ def test_spec_order_is_preserved(tmpdir):
         note_test_deps=True)
 
     new_spec = json.loads(spec_file.read(), object_pairs_hook=OrderedDict)
-    assert new_spec['dependencies'].keys() == ['NoRedInk/top-1', 'NoRedInk/top-2', 'NoRedInk/top-3']
+    assert new_spec.keys() == spec_keys + ['test-dependencies']
+    assert new_spec['dependencies'].keys() == ['NoRedInk/spec-1', 'NoRedInk/spec-2', 'NoRedInk/top-1', 'NoRedInk/top-2', 'NoRedInk/top-3']
+    assert new_spec['test-dependencies'].keys() == ['NoRedInk/spec-1', 'NoRedInk/spec-2']
+
+
+def _make_package(keys, deps):
+    package = OrderedDict((key, package_skeleton[key]) for key in keys)
+    package['dependencies'] = OrderedDict(deps)
+    return package