diff --git a/samcli/commands/deploy/command.py b/samcli/commands/deploy/command.py
index 4da0f09758..957ad22547 100644
--- a/samcli/commands/deploy/command.py
+++ b/samcli/commands/deploy/command.py
@@ -293,17 +293,19 @@ def guided_deploy(
     input_parameter_overrides = {}
 
     color = Colored()
+    start_bold = "\033[1m"
+    end_bold = "\033[0m"
 
     click.echo(
         color.yellow("\n\tSetting default arguments for 'sam deploy'\n\t=========================================")
     )
 
-    stack_name = click.prompt(f"\tStack name", default=stack_name, type=click.STRING)
-    region = click.prompt(f"\tAWS region", default=default_region, type=click.STRING)
+    stack_name = click.prompt(f"\t{start_bold}Stack Name{end_bold}", default=stack_name, type=click.STRING)
+    region = click.prompt(f"\t{start_bold}AWS Region{end_bold}", default=default_region, type=click.STRING)
     if parameter_override_keys:
         for parameter_key, parameter_properties in parameter_override_keys.items():
             input_parameter_overrides[parameter_key] = click.prompt(
-                f"\tParameter {parameter_key}",
+                f"\t{start_bold}Parameter {parameter_key}{end_bold}",
                 default=parameter_overrides.get(
                     parameter_key, parameter_properties.get("Default", "No default specified")
                 ),
@@ -311,21 +313,25 @@ def guided_deploy(
             )
 
     click.secho("\t#Shows you resources changes to be deployed and require a 'Y' to initiate deploy")
-    confirm_changeset = click.confirm(f"\tConfirm changes before deploy", default=confirm_changeset)
+    confirm_changeset = click.confirm(
+        f"\t{start_bold}Confirm changes before deploy{end_bold}", default=confirm_changeset
+    )
     click.secho("\t#SAM needs permission to be able to create roles to connect to the resources in your template")
-    capabilities_confirm = click.confirm(f"\tAllow SAM CLI IAM role creation", default=True)
+    capabilities_confirm = click.confirm(f"\t{start_bold}Allow SAM CLI IAM role creation{end_bold}", default=True)
 
     if not capabilities_confirm:
         input_capabilities = click.prompt(
-            f"\t Capabilities", default=default_capabilities, type=FuncParamType(func=_space_separated_list_func_type)
+            f"\t{start_bold}Capabilities{end_bold}",
+            default=default_capabilities,
+            type=FuncParamType(func=_space_separated_list_func_type),
         )
 
-    save_to_config = click.confirm(f"\tSave arguments to samconfig.toml", default=True)
+    save_to_config = click.confirm(f"\t{start_bold}Save arguments to samconfig.toml{end_bold}", default=True)
 
-    click.echo(color.yellow("\n\tConfiguring deployment s3 bucket\n\t================================"))
+    click.echo(color.yellow("\n\tS3 bucket for deployments\n\t========================="))
     s3_bucket = manage_stack(profile=profile, region=region)
-    click.echo(f"\tUsing deployment bucket: {s3_bucket}")
-    click.echo("\tYou may specify a different default deployment bucket in samconfig.toml")
+    click.echo(f"\tS3 bucket: {s3_bucket}")
+    click.echo("\tA different default S3 bucket can be set in /.samconfig.toml")
 
     return (
         stack_name,
diff --git a/samcli/commands/deploy/deploy_context.py b/samcli/commands/deploy/deploy_context.py
index 58a5270387..e2aa23a058 100644
--- a/samcli/commands/deploy/deploy_context.py
+++ b/samcli/commands/deploy/deploy_context.py
@@ -33,7 +33,7 @@ class DeployContext:
 
     MSG_NO_EXECUTE_CHANGESET = "\nChangeset created successfully. \n"
 
-    MSG_EXECUTE_SUCCESS = "\nSuccessfully created/updated stack - {stack_name}\n"
+    MSG_EXECUTE_SUCCESS = "\nSuccessfully created/updated stack - {stack_name} in {region}\n"
 
     MSG_CONFIRM_CHANGESET = "Confirm deploying?"
     MSG_CONFIRM_CHANGESET_HEADER = "\nPreviewing CloudFormation changeset before deployment"
@@ -111,6 +111,8 @@ def run(self):
 
         self.deployer = Deployer(cloudformation_client)
 
+        region = s3_client._client_config.region_name  # pylint: disable=W0212
+
         return self.deploy(
             self.stack_name,
             template_str,
@@ -121,6 +123,7 @@ def run(self):
             self.notification_arns,
             self.s3_uploader,
             [{"Key": key, "Value": value} for key, value in self.tags.items()] if self.tags else [],
+            region,
             self.fail_on_empty_changeset,
             self.confirm_changeset,
         )
@@ -136,6 +139,7 @@ def deploy(
         notification_arns,
         s3_uploader,
         tags,
+        region,
         fail_on_empty_changeset=True,
         confirm_changeset=False,
     ):
@@ -163,7 +167,7 @@ def deploy(
 
             self.deployer.execute_changeset(result["Id"], stack_name)
             self.deployer.wait_for_execute(stack_name, changeset_type)
-            click.echo(self.MSG_EXECUTE_SUCCESS.format(stack_name=stack_name))
+            click.echo(self.MSG_EXECUTE_SUCCESS.format(stack_name=stack_name, region=region))
 
         except deploy_exceptions.ChangeEmptyError as ex:
             if fail_on_empty_changeset:
diff --git a/samcli/lib/bootstrap/bootstrap.py b/samcli/lib/bootstrap/bootstrap.py
index e093c0fe37..758258b63b 100644
--- a/samcli/lib/bootstrap/bootstrap.py
+++ b/samcli/lib/bootstrap/bootstrap.py
@@ -31,9 +31,9 @@ def _create_or_get_stack(cloudformation_client):
         ds_resp = cloudformation_client.describe_stacks(StackName=SAM_CLI_STACK_NAME)
         stacks = ds_resp["Stacks"]
         stack = stacks[0]
-        LOG.info("\tFound managed SAM CLI stack.")
+        LOG.info("\tLooking for SAM CLI managed stack: Found!")
     except ClientError:
-        LOG.info("\tManaged SAM CLI stack not found, creating.")
+        LOG.info("\tLooking for SAM CLI managed stack: Not found.")
         stack = _create_stack(cloudformation_client)  # exceptions are not captured from subcommands
     # Sanity check for non-none stack? Sanity check for tag?
     tags = stack["Tags"]
@@ -69,6 +69,7 @@ def _create_or_get_stack(cloudformation_client):
 
 
 def _create_stack(cloudformation_client):
+    LOG.info("\tCreating SAM CLI managed stack...")
     change_set_name = "InitialCreation"
     change_set_resp = cloudformation_client.create_change_set(
         StackName=SAM_CLI_STACK_NAME,
@@ -78,7 +79,7 @@ def _create_stack(cloudformation_client):
         ChangeSetName=change_set_name,  # this must be unique for the stack, but we only create so that's fine
     )
     stack_id = change_set_resp["StackId"]
-    LOG.info("\tWaiting for managed stack change set to create.")
+    LOG.info("\tWaiting for managed stack change set to be created.")
     change_waiter = cloudformation_client.get_waiter("change_set_create_complete")
     change_waiter.wait(
         ChangeSetName=change_set_name, StackName=SAM_CLI_STACK_NAME, WaiterConfig={"Delay": 15, "MaxAttempts": 60}
@@ -87,9 +88,9 @@ def _create_stack(cloudformation_client):
     LOG.info("\tWaiting for managed stack to be created.")
     stack_waiter = cloudformation_client.get_waiter("stack_create_complete")
     stack_waiter.wait(StackName=stack_id, WaiterConfig={"Delay": 15, "MaxAttempts": 60})
-    LOG.info("\tManaged SAM CLI stack creation complete.")
     ds_resp = cloudformation_client.describe_stacks(StackName=SAM_CLI_STACK_NAME)
     stacks = ds_resp["Stacks"]
+    LOG.info("\tSuccessfully created SAM CLI managed stack!")
     return stacks[0]
 
 
diff --git a/tests/unit/commands/init/test_cli.py b/tests/unit/commands/init/test_cli.py
index 3c7a9b1274..90088f19b8 100644
--- a/tests/unit/commands/init/test_cli.py
+++ b/tests/unit/commands/init/test_cli.py
@@ -133,12 +133,14 @@ def test_init_cli_interactive_multiple_dep_mgrs(self, generate_project_patch, sd
         # 2: gradle as the dependency manager
         # test-project: response to name
         # N: Don't clone/update the source repo
+        # 1: first app template
         user_input = """
 1
 5
 2
 test-project
 N
+1
         """
         runner = CliRunner()
         result = runner.invoke(init_cmd, input=user_input)