diff --git a/tests/test_keep_alive_timeout.py b/tests/test_keep_alive_timeout.py
index 71c2a6943e..a69ae49bf1 100644
--- a/tests/test_keep_alive_timeout.py
+++ b/tests/test_keep_alive_timeout.py
@@ -17,6 +17,7 @@
 CONFIG_FOR_TESTS = {"KEEP_ALIVE_TIMEOUT": 2, "KEEP_ALIVE": True}
 
 PORT = 42001  # test_keep_alive_timeout_reuse doesn't work with random port
+MAX_LOOPS = 15
 port_counter = count()
 
 
@@ -69,23 +70,35 @@ def test_keep_alive_timeout_reuse():
     """If the server keep-alive timeout and client keep-alive timeout are
     both longer than the delay, the client _and_ server will successfully
     reuse the existing connection."""
-    port = get_port()
-    loop = asyncio.new_event_loop()
-    asyncio.set_event_loop(loop)
-    client = ReusableClient(keep_alive_timeout_app_reuse, loop=loop, port=port)
-    with client:
-        headers = {"Connection": "keep-alive"}
-        request, response = client.get("/1", headers=headers)
-        assert response.status == 200
-        assert response.text == "OK"
-        assert request.protocol.state["requests_count"] == 1
-
-        loop.run_until_complete(aio_sleep(1))
-
-        request, response = client.get("/1")
-        assert response.status == 200
-        assert response.text == "OK"
-        assert request.protocol.state["requests_count"] == 2
+    loops = 0
+    while True:
+        port = get_port()
+        loop = asyncio.new_event_loop()
+        asyncio.set_event_loop(loop)
+        client = ReusableClient(
+            keep_alive_timeout_app_reuse, loop=loop, port=port
+        )
+        try:
+            with client:
+                headers = {"Connection": "keep-alive"}
+                request, response = client.get("/1", headers=headers)
+                assert response.status == 200
+                assert response.text == "OK"
+                assert request.protocol.state["requests_count"] == 1
+
+                loop.run_until_complete(aio_sleep(1))
+
+                request, response = client.get("/1")
+                assert response.status == 200
+                assert response.text == "OK"
+                assert request.protocol.state["requests_count"] == 2
+        except OSError:
+            loops += 1
+            if loops > MAX_LOOPS:
+                raise
+            continue
+        else:
+            break
 
 
 @pytest.mark.skipif(
@@ -97,23 +110,35 @@ def test_keep_alive_timeout_reuse():
 def test_keep_alive_client_timeout():
     """If the server keep-alive timeout is longer than the client
     keep-alive timeout, client will try to create a new connection here."""
-    port = get_port()
-    loop = asyncio.new_event_loop()
-    asyncio.set_event_loop(loop)
-    client = ReusableClient(
-        keep_alive_app_client_timeout, loop=loop, port=port
-    )
-    with client:
-        headers = {"Connection": "keep-alive"}
-        request, response = client.get("/1", headers=headers, timeout=1)
-
-        assert response.status == 200
-        assert response.text == "OK"
-        assert request.protocol.state["requests_count"] == 1
-
-        loop.run_until_complete(aio_sleep(2))
-        request, response = client.get("/1", timeout=1)
-        assert request.protocol.state["requests_count"] == 1
+    loops = 0
+    while True:
+        try:
+            port = get_port()
+            loop = asyncio.new_event_loop()
+            asyncio.set_event_loop(loop)
+            client = ReusableClient(
+                keep_alive_app_client_timeout, loop=loop, port=port
+            )
+            with client:
+                headers = {"Connection": "keep-alive"}
+                request, response = client.get(
+                    "/1", headers=headers, timeout=1
+                )
+
+                assert response.status == 200
+                assert response.text == "OK"
+                assert request.protocol.state["requests_count"] == 1
+
+                loop.run_until_complete(aio_sleep(2))
+                request, response = client.get("/1", timeout=1)
+                assert request.protocol.state["requests_count"] == 1
+        except OSError:
+            loops += 1
+            if loops > MAX_LOOPS:
+                raise
+            continue
+        else:
+            break
 
 
 @pytest.mark.skipif(
@@ -125,24 +150,36 @@ def test_keep_alive_server_timeout():
     keep-alive timeout, the client will either a 'Connection reset' error
     _or_ a new connection. Depending on how the event-loop handles the
     broken server connection."""
-    port = get_port()
-    loop = asyncio.new_event_loop()
-    asyncio.set_event_loop(loop)
-    client = ReusableClient(
-        keep_alive_app_server_timeout, loop=loop, port=port
-    )
-    with client:
-        headers = {"Connection": "keep-alive"}
-        request, response = client.get("/1", headers=headers, timeout=60)
-
-        assert response.status == 200
-        assert response.text == "OK"
-        assert request.protocol.state["requests_count"] == 1
-
-        loop.run_until_complete(aio_sleep(3))
-        request, response = client.get("/1", timeout=60)
-
-        assert request.protocol.state["requests_count"] == 1
+    loops = 0
+    while True:
+        try:
+            port = get_port()
+            loop = asyncio.new_event_loop()
+            asyncio.set_event_loop(loop)
+            client = ReusableClient(
+                keep_alive_app_server_timeout, loop=loop, port=port
+            )
+            with client:
+                headers = {"Connection": "keep-alive"}
+                request, response = client.get(
+                    "/1", headers=headers, timeout=60
+                )
+
+                assert response.status == 200
+                assert response.text == "OK"
+                assert request.protocol.state["requests_count"] == 1
+
+                loop.run_until_complete(aio_sleep(3))
+                request, response = client.get("/1", timeout=60)
+
+                assert request.protocol.state["requests_count"] == 1
+        except OSError:
+            loops += 1
+            if loops > MAX_LOOPS:
+                raise
+            continue
+        else:
+            break
 
 
 @pytest.mark.skipif(
@@ -150,20 +187,34 @@ def test_keep_alive_server_timeout():
     reason="Not testable with current client",
 )
 def test_keep_alive_connection_context():
-    port = get_port()
-    loop = asyncio.new_event_loop()
-    asyncio.set_event_loop(loop)
-    client = ReusableClient(keep_alive_app_context, loop=loop, port=port)
-    with client:
-        headers = {"Connection": "keep-alive"}
-        request1, _ = client.post("/ctx", headers=headers)
-
-        loop.run_until_complete(aio_sleep(1))
-        request2, response = client.get("/ctx")
-
-        assert response.text == "hello"
-        assert id(request1.conn_info.ctx) == id(request2.conn_info.ctx)
-        assert (
-            request1.conn_info.ctx.foo == request2.conn_info.ctx.foo == "hello"
-        )
-        assert request2.protocol.state["requests_count"] == 2
+    loops = 0
+    while True:
+        try:
+            port = get_port()
+            loop = asyncio.new_event_loop()
+            asyncio.set_event_loop(loop)
+            client = ReusableClient(
+                keep_alive_app_context, loop=loop, port=port
+            )
+            with client:
+                headers = {"Connection": "keep-alive"}
+                request1, _ = client.post("/ctx", headers=headers)
+
+                loop.run_until_complete(aio_sleep(1))
+                request2, response = client.get("/ctx")
+
+                assert response.text == "hello"
+                assert id(request1.conn_info.ctx) == id(request2.conn_info.ctx)
+                assert (
+                    request1.conn_info.ctx.foo
+                    == request2.conn_info.ctx.foo
+                    == "hello"
+                )
+                assert request2.protocol.state["requests_count"] == 2
+        except OSError:
+            loops += 1
+            if loops > MAX_LOOPS:
+                raise
+            continue
+        else:
+            break