diff --git a/rsconnect/api.py b/rsconnect/api.py
index 3fd71479..6b09ce14 100644
--- a/rsconnect/api.py
+++ b/rsconnect/api.py
@@ -28,7 +28,7 @@
 from .metadata import ServerStore, AppStore
 from .exception import RSConnectException
 from .bundle import _default_title, fake_module_file_from_directory
-from .timeouts import get_task_timeout
+from .timeouts import get_task_timeout, get_task_timeout_help_message
 
 
 class AbstractRemoteServer:
@@ -313,7 +313,7 @@ def wait_for_task(
         time_slept = 0
         while True:
             if (time.time() - start_time) > timeout:
-                raise RSConnectException("Task timed out after %d seconds" % timeout)
+                raise RSConnectException(get_task_timeout_help_message(timeout))
             elif abort_func():
                 raise RSConnectException("Task aborted.")
 
@@ -1195,7 +1195,7 @@ def wait_until_task_is_successful(self, task_id, timeout=get_task_timeout()):
             time.sleep(2)
 
         if not finished:
-            raise RSConnectException("Application deployment timed out.")
+            raise RSConnectException(get_task_timeout_help_message(timeout))
 
         if status != "success":
             raise RSConnectException("Application deployment failed with error: {}".format(error))
diff --git a/rsconnect/timeouts.py b/rsconnect/timeouts.py
index 77ff1146..82a60374 100644
--- a/rsconnect/timeouts.py
+++ b/rsconnect/timeouts.py
@@ -1,4 +1,6 @@
 import os
+import textwrap
+
 from typing import Union
 
 from rsconnect.exception import RSConnectException
@@ -70,3 +72,18 @@ def get_task_timeout() -> int:
         raise RSConnectException(f"'CONNECT_TASK_TIMEOUT' is set to '{timeout}'. The value must be a positive integer.")
 
     return timeout
+
+
+def get_task_timeout_help_message(timeout=get_task_timeout()) -> str:
+    """Gets a human friendly help message for adjusting the task timeout value."""
+
+    return f"The task timed out after {timeout} seconds." + textwrap.dedent(
+        f"""
+
+        You may try increasing the task timeout value using the {_CONNECT_TASK_TIMEOUT_KEY} environment variable. The default value is {_CONNECT_TASK_TIMEOUT_DEFAULT_VALUE} seconds. The current value is {get_task_timeout()} seconds.
+
+        Example:
+
+            CONNECT_TASK_TIMEOUT={_CONNECT_TASK_TIMEOUT_DEFAULT_VALUE} rsconnect deploy api --server <your-server> --api-key <your-api-key> ./
+        """  # noqa: E501
+    )
diff --git a/tests/test_timeouts.py b/tests/test_timeouts.py
index 2698da09..89b637ed 100644
--- a/tests/test_timeouts.py
+++ b/tests/test_timeouts.py
@@ -4,7 +4,7 @@
 from unittest.mock import patch
 
 from rsconnect.exception import RSConnectException
-from rsconnect.timeouts import get_request_timeout, get_task_timeout
+from rsconnect.timeouts import get_request_timeout, get_task_timeout, get_task_timeout_help_message
 
 
 class GetRequestTimeoutTestCase(TestCase):
@@ -56,3 +56,11 @@ def test_get_negative_timeout_from_environment(self):
         with patch.dict(os.environ, {"CONNECT_TASK_TIMEOUT": "-24"}):
             with self.assertRaises(RSConnectException):
                 get_task_timeout()
+
+class GetTaskTimeoutHelpMessageTestCase(TestCase):
+    def test_get_task_timeout_help_message(self):
+        res = get_task_timeout_help_message(1)
+        self.assertTrue("The task timed out after 1 seconds." in res)
+        self.assertTrue("You may try increasing the task timeout value using the CONNECT_TASK_TIMEOUT environment variable." in res)  # noqa: E501
+        self.assertTrue("The default value is 86400 seconds." in res)
+        self.assertTrue("The current value is 86400 seconds." in res)