diff --git a/libcloud/test/test_connection.py b/libcloud/test/test_connection.py
index d23fa7a829..aa9bf43bf7 100644
--- a/libcloud/test/test_connection.py
+++ b/libcloud/test/test_connection.py
@@ -29,7 +29,12 @@
 from libcloud.test import unittest, no_internet
 from libcloud.utils.py3 import assertRaisesRegex
 from libcloud.common.base import Response, Connection, CertificateConnection
-from libcloud.utils.retry import RETRY_EXCEPTIONS, Retry, RetryForeverOnRateLimitError
+from libcloud.utils.retry import (
+    RETRY_EXCEPTIONS,
+    Retry,
+    MinimalRetry,
+    RetryForeverOnRateLimitError,
+)
 from libcloud.common.exceptions import RateLimitReachedError
 
 
@@ -558,6 +563,32 @@ def responseCls(connection, response) -> mock.MagicMock:
     def _raise_socket_error(self):
         raise socket.gaierror("")
 
+    def test_retry_with_nonpositive_timeout_returns_first_result(self):
+        for retry_class in (MinimalRetry, Retry):
+            for timeout in (0, -1):
+                with self.subTest(retry_class=retry_class, timeout=timeout):
+                    request = Mock(return_value="success")
+                    result = retry_class(timeout=timeout)(request)("/", method="GET")
+                    self.assertEqual(result, "success")
+                    request.assert_called_once_with("/", method="GET")
+
+    @patch("libcloud.utils.retry.time.sleep")
+    def test_retry_with_nonpositive_timeout_preserves_first_error(self, sleep):
+        for retry_class in (MinimalRetry, Retry):
+            for timeout in (0, -1):
+                for error in (
+                    socket.gaierror("unavailable"),
+                    RateLimitReachedError(),
+                    ValueError(),
+                ):
+                    with self.subTest(retry_class=retry_class, timeout=timeout, error=error):
+                        request = Mock(side_effect=error)
+                        with self.assertRaises(type(error)) as exc:
+                            retry_class(timeout=timeout)(request)()
+                        self.assertIs(exc.exception, error)
+                        request.assert_called_once_with()
+        sleep.assert_not_called()
+
     @patch("libcloud.common.base.Connection.request")
     def test_retry_with_sleep(self, mock_connect):
         con = Connection()
diff --git a/libcloud/utils/retry.py b/libcloud/utils/retry.py
index fabb1133b3..def57aa613 100644
--- a/libcloud/utils/retry.py
+++ b/libcloud/utils/retry.py
@@ -107,12 +107,15 @@ def retry_loop(*args, **kwargs):
             end = datetime.now() + timedelta(seconds=self.timeout)
             last_exc = None
 
-            while datetime.now() < end:
+            while last_exc is None or datetime.now() < end:
                 try:
                     return transform_ssl_error(func, *args, **kwargs)
                 except Exception as exc:
                     last_exc = exc
 
+                    if datetime.now() >= end:
+                        raise
+
                     if isinstance(exc, RateLimitReachedError):
                         _logger.debug("You are being rate limited, backing " "off...")