diff --git a/src/deadline/client/cli/_groups/bundle_group.py b/src/deadline/client/cli/_groups/bundle_group.py
index b64fda18..919e5469 100644
--- a/src/deadline/client/cli/_groups/bundle_group.py
+++ b/src/deadline/client/cli/_groups/bundle_group.py
@@ -251,6 +251,11 @@ def _decide_cancel_submission(upload_group: AssetUploadGroup) -> bool:
     is_flag=True,
     help="Allows user to choose Bundle and adds a 'Load a different job bundle' option to the Job-Specific Settings UI",
 )
+@click.option(
+    "--install-gui",
+    is_flag=True,
+    help="Installs GUI dependencies if they are not installed already",
+)
 @click.option(
     "--output",
     type=click.Choice(
@@ -264,13 +269,13 @@ def _decide_cancel_submission(upload_group: AssetUploadGroup) -> bool:
     "parsed/consumed by custom scripts.",
 )
 @_handle_error
-def bundle_gui_submit(job_bundle_dir, browse, output, **args):
+def bundle_gui_submit(job_bundle_dir, browse, output, install_gui, **args):
     """
     Opens GUI to submit an Open Job Description job bundle to AWS Deadline Cloud.
     """
     from ...ui import gui_context_for_cli
 
-    with gui_context_for_cli() as app:
+    with gui_context_for_cli(automatically_install_dependencies=install_gui) as app:
         from ...ui.job_bundle_submitter import show_job_bundle_submitter
 
         if not job_bundle_dir and not browse:
diff --git a/src/deadline/client/cli/_groups/config_group.py b/src/deadline/client/cli/_groups/config_group.py
index 0a68faf1..18c6d882 100644
--- a/src/deadline/client/cli/_groups/config_group.py
+++ b/src/deadline/client/cli/_groups/config_group.py
@@ -83,14 +83,19 @@ def config_show():
 
 
 @cli_config.command(name="gui")
+@click.option(
+    "--install-gui",
+    is_flag=True,
+    help="Installs GUI dependencies if they are not installed already",
+)
 @_handle_error
-def config_gui():
+def config_gui(install_gui: bool):
     """
     Open the workstation configuration settings GUI.
     """
     from ...ui import gui_context_for_cli
 
-    with gui_context_for_cli():
+    with gui_context_for_cli(automatically_install_dependencies=install_gui):
         from ...ui.dialogs.deadline_config_dialog import DeadlineConfigDialog
 
         DeadlineConfigDialog.configure_settings()
diff --git a/src/deadline/client/ui/__init__.py b/src/deadline/client/ui/__init__.py
index b48d22d4..e61dd96e 100644
--- a/src/deadline/client/ui/__init__.py
+++ b/src/deadline/client/ui/__init__.py
@@ -45,19 +45,22 @@ def gui_error_handler(message_title: str, parent: Any = None):
 
 
 @contextmanager
-def gui_context_for_cli():
+def gui_context_for_cli(automatically_install_dependencies: bool):
     """
     A context manager that initializes a Qt GUI context for
     the CLI handler to use.
 
     For example:
 
-    with gui_context_for_cli() as app:
+    with gui_context_for_cli(automatically_install_dependencies) as app:
         from deadline.client.ui.cli_job_submitter import show_cli_job_submitter
 
         show_cli_job_submitter()
 
         app.exec()
+
+    If automatically_install_dependencies is true, dependencies will be installed without prompting the user. Useful
+    if the command is triggered not from a command line.
     """
     import importlib
     import os
@@ -73,11 +76,12 @@ def gui_context_for_cli():
     has_pyside6 = importlib.util.find_spec("PySide6")
     has_pyside2 = importlib.util.find_spec("PySide2")
     if not (has_pyside6 or has_pyside2):
-        message = "Optional GUI components for deadline are unavailable. Would you like to install PySide?"
-        will_install_gui = click.confirm(message, default=False)
-        if not will_install_gui:
-            click.echo("Unable to continue without GUI, exiting")
-            sys.exit(1)
+        if not automatically_install_dependencies:
+            message = "Optional GUI components for deadline are unavailable. Would you like to install PySide?"
+            will_install_gui = click.confirm(message, default=False)
+            if not will_install_gui:
+                click.echo("Unable to continue without GUI, exiting")
+                sys.exit(1)
 
         # this should match what's in the pyproject.toml
         pyside6_pypi = "PySide6-essentials==6.6.*"