diff --git a/src/metagen/src/client_py/static/client.py b/src/metagen/src/client_py/static/client.py
index d77766eb4..d3131ef62 100644
--- a/src/metagen/src/client_py/static/client.py
+++ b/src/metagen/src/client_py/static/client.py
@@ -192,11 +192,13 @@ def selection_to_nodes(
 SelectionT = typing.TypeVar("SelectionT")
 
 
-@dc.dataclass
 class File:
-    content: bytes
-    name: str
-    mimetype: typing.Optional[str] = None
+    def __init__(
+        self, content: bytes, name: str, mimetype: typing.Optional[str] = None
+    ):
+        self.content = content
+        self.name = name
+        self.mimetype = mimetype
 
 
 #
@@ -613,11 +615,21 @@ def build_req(
         if len(files) > 0:
             form_data = MultiPartForm()
             form_data.add_field("operations", body)
+            file_map = {}
             map = {}
 
-            for idx, (path, file) in enumerate(files.items()):
-                map[idx] = ["variables" + path]
-                form_data.add_file(f"{idx}", file)
+            for path, file in files.items():
+                array = file_map.get(file)
+                variable = "variables" + path
+                if array is not None:
+                    array.append(variable)
+                else:
+                    file_map[file] = [variable]
+
+            for idx, (file, variables) in enumerate(file_map.items()):
+                key = str(idx)
+                map[key] = variables
+                form_data.add_file(key, file)
 
             form_data.add_field("map", json.dumps(map))
             headers.update({"Content-type": form_data.get_content_type()})
diff --git a/tests/metagen/metagen_test.ts b/tests/metagen/metagen_test.ts
index 9f6751f6e..3104218d1 100644
--- a/tests/metagen/metagen_test.ts
+++ b/tests/metagen/metagen_test.ts
@@ -656,26 +656,28 @@ Meta.test(
     assertEquals(res.code, 0);
 
     const expectedSchemaU1 = zod.object({
-      upload: zod.boolean(),
+      upload: zod.literal(true),
+    });
+    const expectedSchemaU2 = zod.object({
+      uploadFirst: zod.literal(true),
+      uploadSecond: zod.literal(true),
     });
     const expectedSchemaUn = zod.object({
-      uploadMany: zod.boolean(),
+      uploadMany: zod.literal(true),
     });
 
-    const expectedSchema = zod.tuple([
-      expectedSchemaU1,
-      // expectedSchemaU1,
-      expectedSchemaUn,
-      expectedSchemaU1,
-      expectedSchemaUn,
-    ]);
-
     const cases = [
       {
         name: "client_rs_upload",
         skip: false,
         command: $`cargo run`.cwd(join(scriptsPath, "rs_upload")),
-        expected: expectedSchema,
+        expected: zod.tuple([
+          expectedSchemaU1,
+          // expectedSchemaU1,
+          expectedSchemaUn,
+          expectedSchemaU1,
+          expectedSchemaUn,
+        ]),
       },
       {
         name: "client_py_upload",
@@ -683,7 +685,11 @@ Meta.test(
         command: $`bash -c "python main.py"`.cwd(
           join(scriptsPath, "py_upload"),
         ),
-        expected: zod.tuple([expectedSchemaU1, expectedSchemaUn]),
+        expected: zod.tuple([
+          expectedSchemaU1,
+          expectedSchemaUn,
+          expectedSchemaU2,
+        ]),
       },
       {
         name: "client_ts_upload",
@@ -691,7 +697,11 @@ Meta.test(
         command: $`bash -c "deno run -A main.ts"`.cwd(
           join(scriptsPath, "ts_upload"),
         ),
-        expected: zod.tuple([expectedSchemaU1, expectedSchemaUn]),
+        expected: zod.tuple([
+          expectedSchemaU1,
+          expectedSchemaUn,
+          expectedSchemaU2,
+        ]),
       },
     ];
 
diff --git a/tests/metagen/typegraphs/sample/py/client.py b/tests/metagen/typegraphs/sample/py/client.py
index b45cd8cb4..c1d09cedf 100644
--- a/tests/metagen/typegraphs/sample/py/client.py
+++ b/tests/metagen/typegraphs/sample/py/client.py
@@ -195,11 +195,13 @@ def selection_to_nodes(
 SelectionT = typing.TypeVar("SelectionT")
 
 
-@dc.dataclass
 class File:
-    content: bytes
-    name: str
-    mimetype: typing.Optional[str] = None
+    def __init__(
+        self, content: bytes, name: str, mimetype: typing.Optional[str] = None
+    ):
+        self.content = content
+        self.name = name
+        self.mimetype = mimetype
 
 
 #
@@ -616,11 +618,21 @@ def build_req(
         if len(files) > 0:
             form_data = MultiPartForm()
             form_data.add_field("operations", body)
+            file_map = {}
             map = {}
 
-            for idx, (path, file) in enumerate(files.items()):
-                map[idx] = ["variables" + path]
-                form_data.add_file(f"{idx}", file)
+            for path, file in files.items():
+                array = file_map.get(file)
+                variable = "variables" + path
+                if array is not None:
+                    array.append(variable)
+                else:
+                    file_map[file] = [variable]
+
+            for idx, (file, variables) in enumerate(file_map.items()):
+                key = str(idx)
+                map[key] = variables
+                form_data.add_file(key, file)
 
             form_data.add_field("map", json.dumps(map))
             headers.update({"Content-type": form_data.get_content_type()})
diff --git a/tests/metagen/typegraphs/sample/py_upload/client.py b/tests/metagen/typegraphs/sample/py_upload/client.py
index ec62c7a73..ff3873dfe 100644
--- a/tests/metagen/typegraphs/sample/py_upload/client.py
+++ b/tests/metagen/typegraphs/sample/py_upload/client.py
@@ -195,11 +195,13 @@ def selection_to_nodes(
 SelectionT = typing.TypeVar("SelectionT")
 
 
-@dc.dataclass
 class File:
-    content: bytes
-    name: str
-    mimetype: typing.Optional[str] = None
+    def __init__(
+        self, content: bytes, name: str, mimetype: typing.Optional[str] = None
+    ):
+        self.content = content
+        self.name = name
+        self.mimetype = mimetype
 
 
 #
@@ -616,11 +618,21 @@ def build_req(
         if len(files) > 0:
             form_data = MultiPartForm()
             form_data.add_field("operations", body)
+            file_map = {}
             map = {}
 
-            for idx, (path, file) in enumerate(files.items()):
-                map[idx] = ["variables" + path]
-                form_data.add_file(f"{idx}", file)
+            for path, file in files.items():
+                array = file_map.get(file)
+                variable = "variables" + path
+                if array is not None:
+                    array.append(variable)
+                else:
+                    file_map[file] = [variable]
+
+            for idx, (file, variables) in enumerate(file_map.items()):
+                key = str(idx)
+                map[key] = variables
+                form_data.add_file(key, file)
 
             form_data.add_field("map", json.dumps(map))
             headers.update({"Content-type": form_data.get_content_type()})
diff --git a/tests/metagen/typegraphs/sample/py_upload/main.py b/tests/metagen/typegraphs/sample/py_upload/main.py
index 6282d3321..9f0700f9f 100644
--- a/tests/metagen/typegraphs/sample/py_upload/main.py
+++ b/tests/metagen/typegraphs/sample/py_upload/main.py
@@ -36,4 +36,13 @@
     }
 )
 
-print(json.dumps([res1, res2]))
+file = File(b"Hello", "reusable.txt")
+
+res3 = gql.mutation(
+    {
+        "uploadFirst": api.upload({"file": file, "path": "python/first.txt"}),
+        "uploadSecond": api.upload({"file": file, "path": "python/second.txt"}),
+    }
+)
+
+print(json.dumps([res1, res2, res3]))
diff --git a/tests/metagen/typegraphs/sample/ts_upload/main.ts b/tests/metagen/typegraphs/sample/ts_upload/main.ts
index e14d24856..5f20b59b6 100644
--- a/tests/metagen/typegraphs/sample/ts_upload/main.ts
+++ b/tests/metagen/typegraphs/sample/ts_upload/main.ts
@@ -24,4 +24,11 @@ const res2 = await gql.mutation({
   }),
 });
 
-console.log(JSON.stringify([res1, res2]));
+const file = new File(["Hello"], "reusable.txt", { type: "text/plain" });
+
+const res3 = await gql.mutation({
+  uploadFirst: qg.upload({ file, path: "deno/first.txt" }),
+  uploadSecond: qg.upload({ file, path: "deno/second.txt" }),
+});
+
+console.log(JSON.stringify([res1, res2, res3]));