diff --git a/changelog/5117.improvement.rst b/changelog/5117.improvement.rst
new file mode 100644
index 000000000000..8b2f824ff0bf
--- /dev/null
+++ b/changelog/5117.improvement.rst
@@ -0,0 +1,3 @@
+New command-line argument --conversation-id will be added and wiil give the ability to
+set specific conversation ID for each shell session, if not passed will be random.
+
diff --git a/rasa/cli/shell.py b/rasa/cli/shell.py
index ebbe4ac0dc1e..572ce1424b84 100644
--- a/rasa/cli/shell.py
+++ b/rasa/cli/shell.py
@@ -1,5 +1,6 @@
 import argparse
 import logging
+import uuid
 
 from typing import List
 
@@ -7,7 +8,6 @@
 from rasa.cli.utils import print_error
 from rasa.exceptions import ModelNotFound
 
-
 logger = logging.getLogger(__name__)
 
 
@@ -26,7 +26,15 @@ def add_subparser(
     )
     shell_parser.set_defaults(func=shell)
 
+    shell_parser.add_argument(
+        "--conversation-id",
+        default=uuid.uuid4().hex,
+        required=False,
+        help="Set the conversation ID.",
+    )
+
     run_subparsers = shell_parser.add_subparsers()
+
     shell_nlu_subparser = run_subparsers.add_parser(
         "nlu",
         parents=parents,
@@ -34,6 +42,7 @@ def add_subparser(
         formatter_class=argparse.ArgumentDefaultsHelpFormatter,
         help="Interprets messages on the command line using your NLU model.",
     )
+
     shell_nlu_subparser.set_defaults(func=shell_nlu)
 
     arguments.set_shell_arguments(shell_parser)
diff --git a/rasa/core/channels/console.py b/rasa/core/channels/console.py
index 054b44eb0deb..2fd9b4d8bf13 100644
--- a/rasa/core/channels/console.py
+++ b/rasa/core/channels/console.py
@@ -12,7 +12,6 @@
 from rasa.cli import utils as cli_utils
 from rasa.core import utils
 from rasa.core.channels.channel import RestInput
-from rasa.core.channels.channel import UserMessage
 from rasa.core.constants import DEFAULT_SERVER_URL
 from rasa.core.interpreter import INTENT_MESSAGE_PREFIX
 from rasa.utils.io import DEFAULT_ENCODING
@@ -109,9 +108,9 @@ async def send_message_receive_stream(
 
 
 async def record_messages(
+    sender_id,
     server_url=DEFAULT_SERVER_URL,
     auth_token="",
-    sender_id=UserMessage.DEFAULT_SENDER_ID,
     max_message_limit=None,
     use_response_stream=True,
 ) -> int:
diff --git a/rasa/core/run.py b/rasa/core/run.py
index 9455332624b8..6ec641838ce2 100644
--- a/rasa/core/run.py
+++ b/rasa/core/run.py
@@ -1,5 +1,6 @@
 import asyncio
 import logging
+import uuid
 import os
 import shutil
 from functools import partial
@@ -87,6 +88,7 @@ def configure_app(
     port: int = constants.DEFAULT_SERVER_PORT,
     endpoints: Optional[AvailableEndpoints] = None,
     log_file: Optional[Text] = None,
+    conversation_id: Optional[Text] = uuid.uuid4().hex,
 ):
     """Run the agent."""
     from rasa import server
@@ -124,8 +126,10 @@ async def configure_async_logging():
         async def run_cmdline_io(running_app: Sanic):
             """Small wrapper to shut down the server once cmd io is done."""
             await asyncio.sleep(1)  # allow server to start
+
             await console.record_messages(
-                server_url=constants.DEFAULT_SERVER_FORMAT.format("http", port)
+                server_url=constants.DEFAULT_SERVER_FORMAT.format("http", port),
+                sender_id=conversation_id,
             )
 
             logger.info("Killing Sanic server now.")
@@ -153,6 +157,7 @@ def serve_application(
     ssl_keyfile: Optional[Text] = None,
     ssl_ca_file: Optional[Text] = None,
     ssl_password: Optional[Text] = None,
+    conversation_id: Optional[Text] = uuid.uuid4().hex,
 ):
     from rasa import server
 
@@ -171,6 +176,7 @@ def serve_application(
         port=port,
         endpoints=endpoints,
         log_file=log_file,
+        conversation_id=conversation_id,
     )
 
     ssl_context = server.create_ssl_context(
diff --git a/rasa/core/training/interactive.py b/rasa/core/training/interactive.py
index cad7709162f0..943d493aebf0 100644
--- a/rasa/core/training/interactive.py
+++ b/rasa/core/training/interactive.py
@@ -1624,7 +1624,7 @@ def run_interactive_learning(
     else:
         p = None
 
-    app = run.configure_app(enable_api=True)
+    app = run.configure_app(enable_api=True, conversation_id="default")
     endpoints = AvailableEndpoints.read_endpoints(server_args.get("endpoints"))
 
     # before_server_start handlers make sure the agent is loaded before the
diff --git a/tests/cli/test_rasa_shell.py b/tests/cli/test_rasa_shell.py
index 7301db203ec0..6f156ba1ba3a 100644
--- a/tests/cli/test_rasa_shell.py
+++ b/tests/cli/test_rasa_shell.py
@@ -5,9 +5,10 @@
 def test_shell_help(run: Callable[..., RunResult]):
     output = run("shell", "--help")
 
-    help_text = """usage: rasa shell [-h] [-v] [-vv] [--quiet] [-m MODEL] [--log-file LOG_FILE]
-                  [--endpoints ENDPOINTS] [-p PORT] [-t AUTH_TOKEN]
-                  [--cors [CORS [CORS ...]]] [--enable-api]
+    help_text = """usage: rasa shell [-h] [-v] [-vv] [--quiet]
+                  [--conversation-id CONVERSATION_ID] [-m MODEL]
+                  [--log-file LOG_FILE] [--endpoints ENDPOINTS] [-p PORT]
+                  [-t AUTH_TOKEN] [--cors [CORS [CORS ...]]] [--enable-api]
                   [--remote-storage REMOTE_STORAGE]
                   [--ssl-certificate SSL_CERTIFICATE]
                   [--ssl-keyfile SSL_KEYFILE] [--ssl-ca-file SSL_CA_FILE]
diff --git a/tests/core/test_channels.py b/tests/core/test_channels.py
index d6bedb5e5dcc..3473dfdbfb4e 100644
--- a/tests/core/test_channels.py
+++ b/tests/core/test_channels.py
@@ -114,7 +114,9 @@ async def test_console_input():
             )
 
             await console.record_messages(
-                server_url="https://example.com", max_message_limit=3
+                server_url="https://example.com",
+                max_message_limit=3,
+                sender_id="default",
             )
 
             r = latest_request(