diff --git a/pyproject.toml b/pyproject.toml
index 3a35acd8..272b080b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -9,6 +9,7 @@ dependencies = [
     "databao-context-engine[snowflake]~=0.6.0",
     "prettytable>=3.10.0",
     "databao-agent~=0.2.0",
+    "questionary>=2.1.1",
     "streamlit[snowflake]>=1.53.0",
     "uuid6>=2024.7.10",
     "pyyaml>=6.0",
diff --git a/src/databao_cli/__main__.py b/src/databao_cli/__main__.py
index f61d08a2..49a12ecc 100644
--- a/src/databao_cli/__main__.py
+++ b/src/databao_cli/__main__.py
@@ -4,8 +4,10 @@
 import click
 from click import Context
 
+from databao_cli.labels import LABELS
 from databao_cli.log.logging import configure_logging
 from databao_cli.project.layout import ROOT_DOMAIN, ProjectLayout, find_project
+from databao_cli.utils import ask_confirm, register_labels
 
 
 @click.group()
@@ -24,6 +26,8 @@ def cli(ctx: Context, verbose: bool, project_dir: Path | None) -> None:
     ctx.ensure_object(dict)
     ctx.obj["project_dir"] = project_path
 
+    register_labels(LABELS)
+
     configure_logging(find_project(project_path), verbose=verbose)
 
 
@@ -49,7 +53,7 @@ def init(ctx: Context) -> None:
     try:
         project_layout = init_impl(project_dir)
     except ProjectDirDoesnotExistError:
-        if click.confirm(
+        if ask_confirm(
             f"The directory {project_dir.resolve()} does not exist. Do you want to create it?",
             default=True,
         ):
@@ -69,12 +73,12 @@ def init(ctx: Context) -> None:
     # except RuntimeError as e:
     #     click.echo(str(e), err=True)
 
-    if not click.confirm("\nDo you want to configure a domain now?"):
+    if not ask_confirm("Do you want to configure a domain now?", default=False):
         return
 
     add_datasource_config_interactive_impl(project_layout, ROOT_DOMAIN)
 
-    while click.confirm("\nDo you want to add more datasources?"):
+    while ask_confirm("Do you want to add more datasources?", default=False):
         add_datasource_config_interactive_impl(project_layout, ROOT_DOMAIN)
 
 
diff --git a/src/databao_cli/commands/app.py b/src/databao_cli/commands/app.py
index 00198fb8..113e15b4 100644
--- a/src/databao_cli/commands/app.py
+++ b/src/databao_cli/commands/app.py
@@ -9,7 +9,7 @@
 
 
 def app_impl(ctx: click.Context) -> None:
-    click.echo("Starting Databao UI...")
+    click.echo("Starting Databao web interface...")
 
     try:
         bootstrap_streamlit_app(
@@ -20,7 +20,7 @@ def app_impl(ctx: click.Context) -> None:
             hide_build_context_hint=ctx.obj.get("hide_build_context_hint", False),
         )
     except subprocess.CalledProcessError as e:
-        click.echo(f"Error running Streamlit: {e}", err=True)
+        click.echo(f"Error starting web interface: {e}", err=True)
         sys.exit(1)
     except KeyboardInterrupt:
-        click.echo("\nShutting down Databao...")
+        click.echo("\nShutting down...")
diff --git a/src/databao_cli/commands/ask.py b/src/databao_cli/commands/ask.py
index e72404c8..bb4a92f1 100644
--- a/src/databao_cli/commands/ask.py
+++ b/src/databao_cli/commands/ask.py
@@ -36,7 +36,7 @@ def dataframe_to_prettytable(df: pd.DataFrame, max_rows: int = DEFAULT_MAX_DISPL
 
 
 def initialize_agent_from_dce(project_path: Path, model: str | None, temperature: float) -> Agent:
-    """Initialize the Databao agent using DCE project at the given path."""
+    """Initialize the Databao agent using a Context Engine project at the given path."""
     project = ProjectLayout(project_path)
 
     status = databao_project_status(project)
@@ -49,12 +49,12 @@ def initialize_agent_from_dce(project_path: Path, model: str | None, temperature
 
     if status == DatabaoProjectStatus.NO_DATASOURCES:
         click.echo(
-            f"No datasources configured in project at {project.project_dir}. Add datasources first.",
+            f"No data sources configured in project at {project.project_dir}. Add data sources first",
             err=True,
         )
         sys.exit(1)
 
-    click.echo(f"Using DCE project: {project.project_dir}")
+    click.echo(f"Using Context Engine project: {project.project_dir}")
 
     _domain = create_domain(project.root_domain_dir)
 
@@ -101,18 +101,18 @@ def display_result(thread: Thread) -> None:
 
 def _print_help() -> None:
     """Print help message for interactive mode."""
-    click.echo("Databao REPL")
+    click.echo("Databao interactive chat")
     click.echo("Ask questions about your data in natural language.\n")
     click.echo("Commands:")
-    click.echo("  \\help   - Show this help")
-    click.echo("  \\clear  - Start a new conversation")
+    click.echo("  \\help   - Show this help message")
+    click.echo("  \\clear  - Clear conversation history")
     click.echo("  \\q      - Exit\n")
 
 
 def run_interactive_mode(agent: Agent, show_thinking: bool) -> None:
     """Run the interactive REPL mode."""
-    click.echo("\nDatabao REPL")
-    click.echo("\nType \\help for available commands.\n")
+    click.echo("\nDatabao interactive chat")
+    click.echo("Type \\help for available commands.\n")
 
     writer = _create_cli_writer() if show_thinking else None
 
@@ -148,14 +148,14 @@ def run_interactive_mode(agent: Agent, show_thinking: bool) -> None:
                     stream_ask=show_thinking,
                     writer=writer,
                 )
-                click.echo("Conversation cleared.\n")
+                click.echo("Conversation history cleared.\n")
                 continue
 
             if command == "help":
                 _print_help()
                 continue
 
-            click.echo(f"Unknown command: {user_input}. Type \\help for available commands.\n")
+            click.echo(f"Unknown command: {user_input}\nType \\help for available commands\n")
             continue
 
         # Process as a question
diff --git a/src/databao_cli/commands/context_engine_cli.py b/src/databao_cli/commands/context_engine_cli.py
index 60f5265c..72c41c88 100644
--- a/src/databao_cli/commands/context_engine_cli.py
+++ b/src/databao_cli/commands/context_engine_cli.py
@@ -1,6 +1,8 @@
+import sys
 from typing import Any
 
 import click
+import questionary
 from databao_context_engine import Choice, UserInputCallback
 
 
@@ -15,19 +17,70 @@ def prompt(
         show_default: bool = default_value is not None and default_value != ""
         final_type = click.Choice(type.choices) if isinstance(type, Choice) else str
 
-        # click goes infinite loop if user gives emptry string as an input AND default_value is None
-        # in order to exit this loop we need to set default value to '' (so it gets accepted)
-        #
-        # Code snippet from click:
-        # while True:
-        #   value = prompt_func(prompt)
-        #     if value:
-        #       break
-        #     elif default is not None:
-        #       value = default
-        #       break
-        default_value = default_value if default_value else "" if final_type is str else None
-        return click.prompt(text=text, default=default_value, hide_input=is_secret, type=final_type, show_default=show_default)
+        # Determine if this field is optional
+        is_optional = "(Optional)" in text
+
+        if isinstance(type, Choice):
+            is_interactive = sys.stdin.isatty() and sys.stdout.isatty()
+            if is_interactive:
+                from databao_cli.labels import LABELS
+
+                choices = [questionary.Choice(title=LABELS.get(choice, choice), value=choice) for choice in type.choices]
+                result = questionary.select(
+                    text,
+                    choices=choices,
+                    default=default_value if default_value is not None and default_value in type.choices else None,
+                ).ask()
+                if result is None:
+                    raise click.Abort()
+                return result
+            else:
+                return click.prompt(
+                    text=text,
+                    default=default_value,
+                    hide_input=is_secret,
+                    type=click.Choice(type.choices),
+                    show_default=show_default,
+                )
+
+        if default_value:
+            final_default = default_value
+        elif is_optional:
+            final_default = ""
+        else:
+            final_default = None
+
+        is_interactive = sys.stdin.isatty() and sys.stdout.isatty()
+        if is_interactive and final_type is str:
+            prompt_func = questionary.password if is_secret else questionary.text
+
+            if not is_optional and final_default is None:
+                while True:
+                    result = prompt_func(text, default=final_default or "").ask()
+                    if result is None:
+                        raise click.Abort()
+                    value = str(result).strip()
+                    if value:
+                        return value
+                    click.echo("This field is required and cannot be empty. Please try again.")
+            else:
+                result = prompt_func(text, default=final_default or "").ask()
+                if result is None:
+                    raise click.Abort()
+                return str(result)
+        else:
+            if final_type is str and not is_optional and final_default is None:
+                while True:
+                    value = click.prompt(
+                        text=text, default=final_default, hide_input=is_secret, type=final_type, show_default=show_default
+                    )
+                    if value and value.strip():
+                        return value
+                    click.echo("This field is required and cannot be empty. Please try again.")
+            else:
+                return click.prompt(
+                    text=text, default=final_default, hide_input=is_secret, type=final_type, show_default=show_default
+                )
 
     def confirm(self, text: str) -> bool:
         return click.confirm(text=text)
diff --git a/src/databao_cli/commands/datasource/add_datasource_config.py b/src/databao_cli/commands/datasource/add_datasource_config.py
index b1bb83e2..7974c665 100644
--- a/src/databao_cli/commands/datasource/add_datasource_config.py
+++ b/src/databao_cli/commands/datasource/add_datasource_config.py
@@ -6,10 +6,12 @@
     DatabaoContextPluginLoader,
     DatasourceType,
 )
+from pydantic import ValidationError
 
 from databao_cli.commands.context_engine_cli import ClickUserInputCallback
 from databao_cli.commands.datasource.check_datasource_connection import print_connection_check_results
 from databao_cli.project.layout import ProjectLayout
+from databao_cli.utils import ask_confirm, ask_select, ask_text
 
 
 def add_datasource_config_interactive_impl(project_layout: ProjectLayout, domain: str) -> None:
@@ -21,37 +23,46 @@ def add_datasource_config_interactive_impl(project_layout: ProjectLayout, domain
 
     datasource_type = _ask_for_datasource_type(plugin_loader.get_all_supported_datasource_types(exclude_file_plugins=True))
 
-    datasource_name = click.prompt("Datasource name?", type=str)
+    datasource_name = ask_text("Datasource name?")
 
     datasource_id = domain_manager.datasource_config_exists(datasource_name=datasource_name)
     if datasource_id is not None:
-        click.confirm(
+        ask_confirm(
             f"A config file already exists for this datasource {datasource_id.relative_path_to_config_file()}. "
             f"Do you want to overwrite it?",
             abort=True,
             default=False,
         )
-    created_datasource = domain_manager.create_datasource_config_interactively(
-        datasource_type, datasource_name, ClickUserInputCallback(), overwrite_existing=True
-    )
+
+    while True:
+        try:
+            created_datasource = domain_manager.create_datasource_config_interactively(
+                datasource_type, datasource_name, ClickUserInputCallback(), overwrite_existing=True
+            )
+            break
+        except ValidationError as e:
+            click.echo(click.style("\nValidation error:", fg="red", bold=True))
+            for error in e.errors():
+                field_path = ".".join(str(loc) for loc in error["loc"])
+                click.echo(click.style(f"  • {field_path}: {error['msg']}", fg="red"))
+            click.echo("\nPlease try again with correct values.\n")
 
     datasource_id = created_datasource.datasource.id
     click.echo(
         f"{os.linesep}We've created a new config file for your datasource at: "
         f"{domain_manager.get_config_file_path_for_datasource(datasource_id)}"
     )
-    if click.confirm("\nDo you want to check the connection to this new datasource?"):
+    if ask_confirm("Do you want to check the connection to this new datasource?", default=True):
         results = domain_manager.check_datasource_connection(datasource_ids=[datasource_id])
         print_connection_check_results(domain, results)
 
 
 def _ask_for_datasource_type(supported_datasource_types: set[DatasourceType]) -> DatasourceType:
     all_datasource_types = sorted([ds_type.full_type for ds_type in supported_datasource_types])
-    config_type = click.prompt(
+    config_type = ask_select(
         "What type of datasource do you want to add?",
-        type=click.Choice(all_datasource_types),
-        default=all_datasource_types[0] if len(all_datasource_types) == 1 else None,
+        choices=all_datasource_types,
+        default=None,
     )
-    click.echo(f"Selected type: {config_type}")
 
     return DatasourceType(full_type=config_type)
diff --git a/src/databao_cli/commands/status.py b/src/databao_cli/commands/status.py
index 7737396c..c0779d5a 100644
--- a/src/databao_cli/commands/status.py
+++ b/src/databao_cli/commands/status.py
@@ -28,19 +28,19 @@ def status_impl(project_dir: Path) -> str:
 
 def _generate_info_string(command_info: DceInfo, domain_infos: list[DceDomainInfo]) -> str:
     info_lines = [
-        f"Databao context engine version: {command_info.version}",
-        f"Databao agent version: {version('databao-agent')}",
-        f"Databao context engine storage dir: {command_info.dce_path}",
-        f"Databao context engine plugins: {command_info.plugin_ids}",
+        f"Context Engine version: {command_info.version}",
+        f"Agent version: {version('databao-agent')}",
+        f"Context Engine storage directory: {command_info.dce_path}",
+        f"Context Engine plugins: {command_info.plugin_ids}",
         "",
-        f"OS name: {sys.platform}",
-        f"OS architecture: {os.uname().machine if hasattr(os, 'uname') else 'unknown'}",
+        f"OS: {sys.platform}",
+        f"Architecture: {os.uname().machine if hasattr(os, 'uname') else 'unknown'}",
         "",
     ]
 
     for domain_info in domain_infos:
         if domain_info.is_initialized:
-            info_lines.append(f"Databao Domain dir: {domain_info.project_path.resolve()}")
-            info_lines.append(f"Databao Domain ID: {domain_info.project_id!s}")
+            info_lines.append(f"Domain directory: {domain_info.project_path.resolve()}")
+            info_lines.append(f"Domain ID: {domain_info.project_id!s}")
 
     return os.linesep.join(info_lines)
diff --git a/src/databao_cli/labels.py b/src/databao_cli/labels.py
new file mode 100644
index 00000000..227b30a9
--- /dev/null
+++ b/src/databao_cli/labels.py
@@ -0,0 +1,35 @@
+LABELS = {
+    "athena": "Amazon Athena",
+    "bigquery": "BigQuery",
+    "clickhouse": "ClickHouse",
+    "duckdb": "DuckDB",
+    "mssql": "Microsoft SQL Server",
+    "mysql": "MySQL",
+    "parquet": "Parquet",
+    "postgres": "PostgreSQL",
+    "snowflake": "Snowflake",
+    "sqlite": "SQLite",
+    "BigQueryDefaultAuth": "Default auth",
+    "BigQueryServiceAccountJsonAuth": "Service account JSON credentials",
+    "BigQueryServiceAccountKeyFileAuth": "Service account key file",
+    "SnowflakeKeyPairAuth": "Key pair",
+    "SnowflakePasswordAuth": "Password",
+    "SnowflakeSSOAuth": "SSO",
+    "connection.auth.type": "Authentication type",
+    "connection.host": "Host",
+    "connection.port": "Port",
+    "connection.database": "Database",
+    "connection.schema": "Schema",
+    "connection.username": "Username",
+    "connection.password": "Password",
+    "connection.account": "Account",
+    "connection.warehouse": "Warehouse",
+    "connection.role": "Role",
+    "connection.path": "File path",
+    "connection.project": "Project",
+    "connection.dataset": "Dataset",
+    "connection.location": "Location",
+    "connection.auth.credentials_file": "Credentials file",
+    "connection.auth.key_file": "Key file",
+    "connection.auth.token": "Token",
+}
diff --git a/src/databao_cli/mcp/tools/databao_ask/agent_factory.py b/src/databao_cli/mcp/tools/databao_ask/agent_factory.py
index b4645e7b..f9e6ba2d 100644
--- a/src/databao_cli/mcp/tools/databao_ask/agent_factory.py
+++ b/src/databao_cli/mcp/tools/databao_ask/agent_factory.py
@@ -19,7 +19,7 @@ def create_agent_for_tool(
     executor: str = "claude_code",
     cache: Cache | None = None,
 ) -> Agent:
-    """Create a Databao agent from a DCE project, configured for MCP tool use.
+    """Create a Databao agent from a Context Engine project, configured for MCP tool use.
 
     Raises ValueError if the project is not ready (no datasources, no build).
     """
@@ -27,11 +27,11 @@ def create_agent_for_tool(
 
     status = databao_project_status(project)
     if status == DatabaoProjectStatus.NOT_INITIALIZED:
-        raise ValueError("Databao project is not initialized. Run 'databao init' first.")
+        raise ValueError("Databao project is not initialized. Run 'databao init' first")
     if status == DatabaoProjectStatus.NO_DATASOURCES:
-        raise ValueError("No datasources configured. Run 'databao datasource add' first.")
+        raise ValueError("No data sources configured. Run 'databao datasource add' first")
     if not has_build_output(project):
-        raise ValueError("Project has no build output. Run 'databao build' first.")
+        raise ValueError("Project has no build output. Run 'databao build' first")
 
     domain = create_domain(project.root_domain_dir)
 
diff --git a/src/databao_cli/utils.py b/src/databao_cli/utils.py
new file mode 100644
index 00000000..cd319c05
--- /dev/null
+++ b/src/databao_cli/utils.py
@@ -0,0 +1,76 @@
+import sys
+from typing import Any
+
+import click
+import questionary
+
+_labels: dict[str, str] = {}
+
+
+def register_labels(labels: dict[str, str]) -> None:
+    _labels.update(labels)
+
+
+def _resolve(value: str) -> tuple[str, str]:
+    label = _labels.get(value, value)
+    return value, label
+
+
+def is_interactive() -> bool:
+    """True when running in an interactive terminal."""
+    return sys.stdin.isatty() and sys.stdout.isatty()
+
+
+def ask_select(message: str, choices: list[str], default: str | None = None) -> str:
+    """Select from a list. Interactive in TTY, plain text otherwise."""
+    if is_interactive():
+        resolved = [_resolve(c) if isinstance(c, str) else c for c in choices]
+        q_choices = [questionary.Choice(title=label, value=value) for value, label in resolved]
+        result: Any = questionary.select(message, choices=q_choices, default=default).ask()
+        if result is None:
+            raise click.Abort()
+        return str(result)
+    else:
+        click.echo(f"{message}")
+        for i, choice in enumerate(choices, 1):
+            click.echo(f"  {i}. {choice}")
+        value: str = click.prompt(
+            "Enter a number of value",
+            default=default or choices[0],
+        )
+        if value.isdigit() and 1 <= int(value) <= len(choices):
+            return choices[int(value) - 1]
+        if value in choices:
+            return value
+        raise click.BadParameter(f"Invalid choice: {value}")
+
+
+def ask_confirm(message: str, default: bool = True, abort: bool = False) -> bool:
+    """Yes/no. Fancy in TTY, plain click.confirm otherwise."""
+    if is_interactive():
+        result: Any = questionary.confirm(message, default=default).ask()
+        if result is None:
+            raise click.Abort()
+        if abort and not result:
+            raise click.Abort()
+        return bool(result)
+    else:
+        return click.confirm(message, default=default, abort=abort)
+
+
+def ask_text(message: str, default: str | None = None, allow_empty: bool = False) -> str:
+    """Text input. Interactive in TTY, plain click.prompt otherwise."""
+    if is_interactive():
+        while True:
+            try:
+                result: Any = questionary.text(message, default=default or "").ask()
+            except KeyboardInterrupt:
+                raise click.Abort() from None
+            if result is None:
+                raise click.Abort()
+            value = str(result)
+            if value.strip() or allow_empty:
+                return value
+            click.echo("Value cannot be empty. Please try again.")
+    else:
+        return str(click.prompt(message, default=default))
diff --git a/tests/test_add_datasource.py b/tests/test_add_datasource.py
index 6265fe3a..b07124fb 100644
--- a/tests/test_add_datasource.py
+++ b/tests/test_add_datasource.py
@@ -1,7 +1,9 @@
 from pathlib import Path
+from unittest.mock import Mock
 
 import duckdb
 import pytest
+import questionary
 from click.testing import CliRunner
 
 from databao_cli.__main__ import cli
@@ -31,11 +33,14 @@ def temp_parquet_file(request: pytest.FixtureRequest, tmp_path: Path) -> Path:
     return parquet_file
 
 
-def test_databao_datasource_add(tmp_path: Path, temp_parquet_file: Path) -> None:
+def test_databao_datasource_add(tmp_path: Path, temp_parquet_file: Path, monkeypatch: pytest.MonkeyPatch) -> None:
     init_databao_project(tmp_path)
 
+    prompt = Mock()
+    prompt.ask.return_value = "parquet"
+    monkeypatch.setattr(questionary, "select", Mock(return_value=prompt))
+
     inputs = [
-        "parquet",
         "resources/my_parq",
         str(temp_parquet_file),
         "N",  # No. skip adding duckdb secret
diff --git a/uv.lock b/uv.lock
index c8933823..e9bd80e7 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1009,6 +1009,7 @@ dependencies = [
     { name = "nh3" },
     { name = "prettytable" },
     { name = "pyyaml" },
+    { name = "questionary" },
     { name = "streamlit", extra = ["snowflake"] },
     { name = "uuid6" },
 ]
@@ -1065,6 +1066,7 @@ requires-dist = [
     { name = "nh3", specifier = ">=0.2.15" },
     { name = "prettytable", specifier = ">=3.10.0" },
     { name = "pyyaml", specifier = ">=6.0" },
+    { name = "questionary", specifier = ">=2.1.1" },
     { name = "streamlit", extras = ["snowflake"], specifier = ">=1.53.0" },
     { name = "uuid6", specifier = ">=2024.7.10" },
 ]
@@ -1921,7 +1923,6 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/ec/e8/2e1462c8fdbe0f210feb5ac7ad2d9029af8be3bf45bd9fa39765f821642f/greenlet-3.3.1-cp311-cp311-macosx_11_0_universal2.whl", hash = "sha256:5fd23b9bc6d37b563211c6abbb1b3cab27db385a4449af5c32e932f93017080c", size = 274974, upload-time = "2026-01-23T15:31:02.891Z" },
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