diff --git a/tests/api/test_bootstrap_multiple_spec.py b/tests/api/test_bootstrap_multiple_spec.py
new file mode 100644
index 000000000..96b8af59c
--- /dev/null
+++ b/tests/api/test_bootstrap_multiple_spec.py
@@ -0,0 +1,49 @@
+import json
+
+import pytest
+from connexion import App
+
+from conftest import TEST_FOLDER
+
+SPECS = [
+    pytest.param(
+        [
+            {"specification": "swagger_greeting.yaml", "name": "greeting"},
+            {"specification": "swagger_bye.yaml", "name": "bye"},
+        ],
+        id="swagger",
+    ),
+    pytest.param(
+        [
+            {"specification": "openapi_greeting.yaml", "name": "greeting"},
+            {"specification": "openapi_bye.yaml", "name": "bye"},
+        ],
+        id="openapi",
+    ),
+]
+
+
+@pytest.mark.parametrize("spec", SPECS)
+def test_app_with_multiple_definition(multiple_yaml_same_basepath_dir, spec):
+    # Create the app with a relative path and run the test_app testcase below.
+    app = App(
+        __name__,
+        port=5001,
+        specification_dir=".."
+        / multiple_yaml_same_basepath_dir.relative_to(TEST_FOLDER),
+        debug=True,
+    )
+
+    for s in spec:
+        app.add_api(**s)
+
+    app_client = app.app.test_client()
+
+    post_greeting = app_client.post("/v1.0/greeting/jsantos")  # type: flask.Response
+    assert post_greeting.status_code == 200
+    greeting_response = json.loads(post_greeting.data.decode("utf-8"))
+    assert greeting_response["greeting"] == "Hello jsantos"
+
+    get_bye = app_client.get("/v1.0/bye/jsantos")  # type: flask.Response
+    assert get_bye.status_code == 200
+    assert get_bye.data == b"Goodbye jsantos"
diff --git a/tests/conftest.py b/tests/conftest.py
index 92a125def..098526339 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -142,6 +142,11 @@ def json_validation_spec_dir():
     return FIXTURES_FOLDER / "json_validation"
 
 
+@pytest.fixture
+def multiple_yaml_same_basepath_dir():
+    return FIXTURES_FOLDER / "multiple_yaml_same_basepath"
+
+
 @pytest.fixture(scope="session")
 def json_datetime_dir():
     return FIXTURES_FOLDER / "datetime_support"
diff --git a/tests/fixtures/multiple_yaml_same_basepath/openapi_bye.yaml b/tests/fixtures/multiple_yaml_same_basepath/openapi_bye.yaml
new file mode 100644
index 000000000..1970a9b15
--- /dev/null
+++ b/tests/fixtures/multiple_yaml_same_basepath/openapi_bye.yaml
@@ -0,0 +1,28 @@
+openapi: 3.0.0
+info:
+  title: '{{title}}'
+  version: '1.0'
+paths:
+  '/bye/{name}':
+    get:
+      summary: Generate goodbye
+      description: Generates a goodbye message.
+      operationId: fakeapi.hello.get_bye
+      responses:
+        '200':
+          description: goodbye response
+          content:
+            text/plain:
+              schema:
+                type: string
+        default:
+          description: unexpected error
+      parameters:
+        - name: name
+          in: path
+          description: Name of the person to say bye.
+          required: true
+          schema:
+            type: string
+servers:
+  - url: /v1.0
diff --git a/tests/fixtures/multiple_yaml_same_basepath/openapi_greeting.yaml b/tests/fixtures/multiple_yaml_same_basepath/openapi_greeting.yaml
new file mode 100644
index 000000000..249718068
--- /dev/null
+++ b/tests/fixtures/multiple_yaml_same_basepath/openapi_greeting.yaml
@@ -0,0 +1,28 @@
+openapi: 3.0.0
+info:
+  title: '{{title}}'
+  version: '1.0'
+paths:
+  '/greeting/{name}':
+    post:
+      summary: Generate greeting
+      description: Generates a greeting message.
+      operationId: fakeapi.hello.post_greeting
+      responses:
+        '200':
+          description: greeting response
+          content:
+            '*/*':
+              schema:
+                type: object
+      parameters:
+        - name: name
+          in: path
+          description: Name of the person to greet.
+          required: true
+          schema:
+            type: string
+
+      
+servers:
+  - url: /v1.0
diff --git a/tests/fixtures/multiple_yaml_same_basepath/swagger_bye.yaml b/tests/fixtures/multiple_yaml_same_basepath/swagger_bye.yaml
new file mode 100644
index 000000000..2905e126c
--- /dev/null
+++ b/tests/fixtures/multiple_yaml_same_basepath/swagger_bye.yaml
@@ -0,0 +1,29 @@
+swagger: "2.0"
+
+info:
+  title: "{{title}}"
+  version: "1.0"
+
+basePath: /v1.0
+
+paths:
+  /bye/{name}:
+    get:
+      summary: Generate goodbye
+      description: Generates a goodbye message.
+      operationId: fakeapi.hello.get_bye
+      produces:
+        - text/plain
+      responses:
+        '200':
+          description: goodbye response
+          schema:
+            type: string
+        default:
+          description: "unexpected error"
+      parameters:
+        - name: name
+          in: path
+          description: Name of the person to say bye.
+          required: true
+          type: string
diff --git a/tests/fixtures/multiple_yaml_same_basepath/swagger_greeting.yaml b/tests/fixtures/multiple_yaml_same_basepath/swagger_greeting.yaml
new file mode 100644
index 000000000..f3246b530
--- /dev/null
+++ b/tests/fixtures/multiple_yaml_same_basepath/swagger_greeting.yaml
@@ -0,0 +1,25 @@
+swagger: "2.0"
+
+info:
+  title: "{{title}}"
+  version: "1.0"
+
+basePath: /v1.0
+
+paths:
+ /greeting/{name}:
+    post:
+      summary: Generate greeting
+      description: Generates a greeting message.
+      operationId: fakeapi.hello.post_greeting
+      responses:
+        200:
+          description: greeting response
+          schema:
+            type: object
+      parameters:
+        - name: name
+          in: path
+          description: Name of the person to greet.
+          required: true
+          type: string
\ No newline at end of file