diff --git a/cli/cmd/bootstrap-tenant-config-repo/bootstrap-tenant-config-repo.go b/cli/cmd/bootstrap-tenant-config-repo/bootstrap-tenant-config-repo.go
index 06460469..d6f34257 100644
--- a/cli/cmd/bootstrap-tenant-config-repo/bootstrap-tenant-config-repo.go
+++ b/cli/cmd/bootstrap-tenant-config-repo/bootstrap-tenant-config-repo.go
@@ -218,7 +218,7 @@ pipeline to receive an initial +/-1 Verified vote.`,
 						getAnsibleIncludeRole("remove-zuul-sshkey"),
 					},
 					"run_once": true,
-					"when":     "ansible_connection != 'kubectl'",
+					"when":     "ansible_connection == 'kubectl'",
 				},
 				{
 					"import_role": map[string]string{
diff --git a/doc/reference/CHANGELOG.md b/doc/reference/CHANGELOG.md
index 2e0bc964..ae01e45a 100644
--- a/doc/reference/CHANGELOG.md
+++ b/doc/reference/CHANGELOG.md
@@ -8,6 +8,9 @@ All notable changes to this project will be documented in this file.
 ### Removed
 ### Changed
 ### Fixed
+
+SF bootstrap-tenant command - fix the base pre-run playbook for container based job (wrong condition check)
+
 ### Security
 
 ## [v0.0.43] - 2024-09-20