diff --git a/sdks/python/setup.py b/sdks/python/setup.py
index f6c70cbe2d..73d513259f 100644
--- a/sdks/python/setup.py
+++ b/sdks/python/setup.py
@@ -47,7 +47,6 @@
         "pytest",
         "rich",
         "tqdm",
-        "questionary",
         "uuid7<1.0.0",
     ],
     entry_points={
diff --git a/sdks/python/src/opik/cli.py b/sdks/python/src/opik/cli.py
index 071348b8ef..37b68b8d4d 100644
--- a/sdks/python/src/opik/cli.py
+++ b/sdks/python/src/opik/cli.py
@@ -1,11 +1,13 @@
 """CLI tool for Opik."""
 
+import logging
 from importlib import metadata
 
 import click
-import questionary
-
 from opik.configurator import configure as opik_configure
+from opik.configurator import interactive_helpers
+
+LOGGER = logging.getLogger(__name__)
 
 __version__: str = "0.0.0+dev"
 if __package__:
@@ -35,30 +37,30 @@ def configure(use_local: bool) -> None:
     if use_local:
         opik_configure.configure(use_local=True, force=True)
     else:
-        deployment_type_choice = questionary.select(
-            "Which Opik deployment do you want to log your traces to?",
-            choices=["Opik Cloud", "Self-hosted Comet platform", "Local deployment"],
-        ).unsafe_ask()
+        deployment_type_choice = interactive_helpers.ask_user_for_deployment_type()
 
-        if deployment_type_choice == "Opik Cloud":
+        if deployment_type_choice == interactive_helpers.DeploymentType.CLOUD:
             configurator = opik_configure.OpikConfigurator(
                 url=opik_configure.OPIK_BASE_URL_CLOUD,
                 use_local=False,
                 force=True,
                 self_hosted_comet=False,
             )
-        elif deployment_type_choice == "Self-hosted Comet platform":
+        elif deployment_type_choice == interactive_helpers.DeploymentType.SELF_HOSTED:
             configurator = opik_configure.OpikConfigurator(
                 use_local=False,
                 force=True,
                 self_hosted_comet=True,
             )
-        else:
+        elif deployment_type_choice == interactive_helpers.DeploymentType.LOCAL:
             configurator = opik_configure.OpikConfigurator(
                 use_local=True,
                 force=True,
                 self_hosted_comet=False,
             )
+        else:
+            LOGGER.error("Unknown deployment type was selected. Exiting.")
+            exit(1)
 
         configurator.configure()
 
diff --git a/sdks/python/src/opik/configurator/interactive_helpers.py b/sdks/python/src/opik/configurator/interactive_helpers.py
index 6b7d5409e5..6ffbbfd1bf 100644
--- a/sdks/python/src/opik/configurator/interactive_helpers.py
+++ b/sdks/python/src/opik/configurator/interactive_helpers.py
@@ -1,3 +1,4 @@
+import enum
 import logging
 import sys
 
@@ -95,3 +96,56 @@ def ask_user_for_approval(message: str) -> bool:
         if users_choice in ("N", "NO"):
             return False
         LOGGER.error("Wrong choice. Please try again.")
+
+
+class DeploymentType(enum.Enum):
+    CLOUD = (1, "Opik Cloud (default)")
+    SELF_HOSTED = (2, "Self-hosted Comet platform")
+    LOCAL = (3, "Local deployment")
+
+    @classmethod
+    def find_by_value(cls, value: int) -> "DeploymentType":
+        """
+        Find the DeploymentType by its integer value.
+
+        :param value: The integer value of the DeploymentType.
+        :return: The corresponding DeploymentType.
+        """
+        for v in cls:
+            if v.value[0] == value:
+                return v
+        raise ValueError(f"No DeploymentType with value '{value}'")
+
+
+def ask_user_for_deployment_type() -> DeploymentType:
+    """
+    Asks the user to select a deployment type from the available Opik deployment options.
+    Prompts the user until a valid selection is made.
+
+    Returns:
+        DeploymentType: The user's selected deployment type.
+    """
+    msg = ["Which Opik deployment do you want to log your traces to?"]
+
+    for deployment in DeploymentType:
+        msg.append(f"{deployment.value[0]} - {deployment.value[1]}")
+
+    msg.append("\n> ")
+
+    message_string = "\n".join(msg)
+
+    while True:
+        choice_str = input(message_string).strip()
+
+        if choice_str not in ("1", "2", "3", ""):
+            LOGGER.error("Wrong choice. Please try again.\n")
+            continue
+
+        if choice_str == "":
+            choice_index = 1
+        else:
+            choice_index = int(choice_str)
+
+        choice = DeploymentType.find_by_value(choice_index)
+
+        return choice