diff --git a/conf/capsule.yaml.template b/conf/capsule.yaml.template
index e6747faa5eb..9ef9e48a2c2 100644
--- a/conf/capsule.yaml.template
+++ b/conf/capsule.yaml.template
@@ -10,6 +10,8 @@ CAPSULE:
     # The base os rhel version where the capsule installed
     # RHEL_VERSION:
   # The Ansible Tower workflow used to deploy a capsule
-  DEPLOY_WORKFLOW: deploy-capsule
+  DEPLOY_WORKFLOWS:
+    PRODUCT: deploy-capsule  # workflow to deploy OS with product running on top of it
+    OS: deploy-rhel  # workflow to deploy OS that is ready to run the product
   # Dictionary of arguments which should be passed along to the deploy workflow
   DEPLOY_ARGUMENTS:
diff --git a/conf/dynaconf_hooks.py b/conf/dynaconf_hooks.py
index 116207aa165..6d09d6e5bec 100644
--- a/conf/dynaconf_hooks.py
+++ b/conf/dynaconf_hooks.py
@@ -1,5 +1,9 @@
+from inspect import getmembers, isfunction
 import json
 from pathlib import Path
+import sys
+
+from box import Box
 
 from robottelo.logging import logger
 from robottelo.utils.ohsnap import dogfood_repository
@@ -22,6 +26,7 @@ def post(settings):
             )
             data = get_repos_config(settings)
             write_cache(settings_cache_path, data)
+    config_migrations(settings, data)
     data['dynaconf_merge'] = True
     return data
 
@@ -33,7 +38,32 @@ def write_cache(path, data):
 
 def read_cache(path):
     logger.info(f'Using settings cache file: {path}')
-    return json.loads(path.read_text())
+    return Box(json.loads(path.read_text()))
+
+
+def config_migrations(settings, data):
+    """Run config migrations
+
+    Fetch the config migrations from the conf/migrations.py file and run them.
+
+    :param settings: dynaconf settings object
+    :type settings: LazySettings
+    :param data: settings data to be merged with the rest of the settings
+    :type data: dict
+    """
+    logger.info('Running config migration hooks')
+    sys.path.append(str(Path(__file__).parent))
+    from conf import migrations
+
+    migration_functions = [
+        mf for mf in getmembers(migrations, isfunction) if mf[0].startswith('migration_')
+    ]
+    # migration_functions is a sorted list of tuples (name, function)
+    for name, func in migration_functions:
+        logger.debug(f'Running {name}')
+        func(settings, data)
+        logger.debug(f'Finished running {name}')
+    logger.info('Finished running config migration hooks')
 
 
 def get_repos_config(settings):
@@ -46,7 +76,7 @@ def get_repos_config(settings):
             'The Ohsnap URL is invalid! Post-configuration hooks will not run. '
             'Default configuration will be used.'
         )
-    return {'REPOS': data}
+    return Box({'REPOS': data})
 
 
 def get_ohsnap_repos(settings):
diff --git a/conf/migrations.py b/conf/migrations.py
new file mode 100644
index 00000000000..b263fa352d6
--- /dev/null
+++ b/conf/migrations.py
@@ -0,0 +1,37 @@
+"""Robottelo configuration migrations
+
+This module contains functions that are run after the configuration is loaded. Each function
+should be named `migration_<YYMMDD>_<description>` and accept two parameters: `settings` and
+`data`. `settings` is a `dynaconf` `Box` object containing the configuration. `data` is a
+`dict` that can be used to store settings that will be merged with the rest of the settings.
+The functions should not return anything.
+"""
+
+from packaging.version import Version
+
+from robottelo.logging import logger
+
+
+def migration_231129_deploy_workflow(settings, data):
+    """Migrates {server,capsule}.deploy_workflow to {server,capsule}.deploy_workflows"""
+    for product_type in ['server', 'capsule']:
+        # If the product_type has a deploy_workflow and it is a string, and
+        # it does not have a deploy_workflows set
+        if (
+            settings[product_type].get('deploy_workflow')
+            and isinstance(settings[product_type].deploy_workflow, str)
+            and not settings[product_type].get('deploy_workflows')
+        ):
+            sat_rhel_version = settings[product_type].version.rhel_version
+            data[product_type] = {}
+            # Set the deploy_workflows to a dict with product and os keys
+            # Get the OS workflow from the content_host config
+            data[product_type].deploy_workflows = {
+                'product': settings[product_type].deploy_workflow,
+                'os': settings.content_host[
+                    f'rhel{Version(str(sat_rhel_version)).major}'
+                ].vm.workflow,
+            }
+            logger.info(
+                f'Migrated {product_type}.DEPLOY_WORKFLOW to {product_type}.DEPLOY_WORKFLOWS'
+            )
diff --git a/conf/server.yaml.template b/conf/server.yaml.template
index 7f876bccaba..c5b844e6509 100644
--- a/conf/server.yaml.template
+++ b/conf/server.yaml.template
@@ -27,7 +27,9 @@ SERVER:
   # this setting determines if they will be automatically checked in
   AUTO_CHECKIN: False
   # The Ansible Tower workflow used to deploy a satellite
-  DEPLOY_WORKFLOW: "deploy-sat-jenkins"
+  DEPLOY_WORKFLOWS:
+    PRODUCT: deploy-satellite  # workflow to deploy OS with product running on top of it
+    OS: deploy-rhel  # workflow to deploy OS that is ready to run the product
   # Dictionary of arguments which should be passed along to the deploy workflow
   # DEPLOY_ARGUMENTS:
   # HTTP scheme when building the server URL
diff --git a/pytest_fixtures/core/sat_cap_factory.py b/pytest_fixtures/core/sat_cap_factory.py
index 8f83704702e..436d8b6d443 100644
--- a/pytest_fixtures/core/sat_cap_factory.py
+++ b/pytest_fixtures/core/sat_cap_factory.py
@@ -63,7 +63,7 @@ def factory(retry_limit=3, delay=300, workflow=None, **broker_args):
 
         vmb = Broker(
             host_class=Satellite,
-            workflow=workflow or settings.server.deploy_workflow,
+            workflow=workflow or settings.server.deploy_workflows.product,
             **broker_args,
         )
         timeout = (1200 + delay) * retry_limit
@@ -95,7 +95,7 @@ def factory(retry_limit=3, delay=300, workflow=None, **broker_args):
             broker_args.update(settings.capsule.deploy_arguments)
         vmb = Broker(
             host_class=Capsule,
-            workflow=workflow or settings.capsule.deploy_workflow,
+            workflow=workflow or settings.capsule.deploy_workflows.product,
             **broker_args,
         )
         timeout = (1200 + delay) * retry_limit
@@ -202,7 +202,7 @@ def module_lb_capsule(retry_limit=3, delay=300, **broker_args):
         timeout = (1200 + delay) * retry_limit
         hosts = Broker(
             host_class=Capsule,
-            workflow=settings.capsule.deploy_workflow,
+            workflow=settings.capsule.deploy_workflows.product,
             _count=2,
             **broker_args,
         )
@@ -245,12 +245,13 @@ def parametrized_enrolled_sat(
 
 
 def get_deploy_args(request):
+    """Get deploy arguments for Satellite base OS deployment. Should not be used for Capsule."""
     rhel_version = get_sat_rhel_version()
     deploy_args = {
         'deploy_rhel_version': rhel_version.base_version,
         'deploy_flavor': settings.flavors.default,
         'promtail_config_template_file': 'config_sat.j2',
-        'workflow': settings.content_host.get(f'rhel{rhel_version.major}').vm.workflow,
+        'workflow': settings.server.deploy_workflows.os,
     }
     if hasattr(request, 'param'):
         if isinstance(request.param, dict):
@@ -277,11 +278,11 @@ def module_sat_ready_rhels(request):
 @pytest.fixture
 def cap_ready_rhel():
     rhel_version = Version(settings.capsule.version.release)
-    settings.content_host.get(f'rhel{rhel_version.major}').vm.workflow
     deploy_args = {
         'deploy_rhel_version': rhel_version.base_version,
         'deploy_flavor': settings.flavors.default,
-        'workflow': settings.content_host.get(f'rhel{rhel_version.major}').vm.workflow,
+        'promtail_config_template_file': 'config_sat.j2',
+        'workflow': settings.capsule.deploy_workflows.os,
     }
     with Broker(**deploy_args, host_class=Capsule) as host:
         yield host
diff --git a/robottelo/config/validators.py b/robottelo/config/validators.py
index 383abfb7aed..f598821839d 100644
--- a/robottelo/config/validators.py
+++ b/robottelo/config/validators.py
@@ -23,7 +23,9 @@
         ),
         Validator('server.admin_password', default='changeme'),
         Validator('server.admin_username', default='admin'),
-        Validator('server.deploy_workflow', must_exist=True),
+        Validator('server.deploy_workflows', must_exist=True, is_type_of=dict),
+        Validator('server.deploy_workflows.product', must_exist=True),
+        Validator('server.deploy_workflows.os', must_exist=True),
         Validator('server.deploy_arguments', must_exist=True, is_type_of=dict, default={}),
         Validator('server.scheme', default='https'),
         Validator('server.port', default=443),
@@ -67,7 +69,9 @@
     capsule=[
         Validator('capsule.version.release', must_exist=True),
         Validator('capsule.version.source', must_exist=True),
-        Validator('capsule.deploy_workflow', must_exist=True),
+        Validator('capsule.deploy_workflows', must_exist=True, is_type_of=dict),
+        Validator('capsule.deploy_workflows.product', must_exist=True),
+        Validator('capsule.deploy_workflows.os', must_exist=True),
         Validator('capsule.deploy_arguments', must_exist=True, is_type_of=dict, default={}),
     ],
     certs=[
diff --git a/robottelo/hosts.py b/robottelo/hosts.py
index 4c35dbd41d5..9b1ef870b1a 100644
--- a/robottelo/hosts.py
+++ b/robottelo/hosts.py
@@ -74,7 +74,7 @@ def lru_sat_ready_rhel(rhel_ver):
         'deploy_rhel_version': rhel_version,
         'deploy_flavor': settings.flavors.default,
         'promtail_config_template_file': 'config_sat.j2',
-        'workflow': settings.content_host.get(f'rhel{Version(rhel_version).major}').vm.workflow,
+        'workflow': settings.server.deploy_workflows.os,
     }
     sat_ready_rhel = Broker(**deploy_args, host_class=Satellite).checkout()
     return sat_ready_rhel