diff --git a/internal/constants/constants.go b/internal/constants/constants.go
index f6f5e334..9abab1db 100644
--- a/internal/constants/constants.go
+++ b/internal/constants/constants.go
@@ -11,6 +11,7 @@ const (
 	// prompt constants
 
 	MaxPnameLength     = 16
+	MaxOnameLength     = 39
 	RegexValidation    = "regex"
 	FunctionValidation = "function"
 	ZeroReleaseURL     = "https://github.com/commitdev/zero/releases"
diff --git a/internal/init/init.go b/internal/init/init.go
index a0ddfc11..04520e49 100644
--- a/internal/init/init.go
+++ b/internal/init/init.go
@@ -130,12 +130,12 @@ func getProjectPrompts(projectName string, modules map[string]moduleconfig.Modul
 		"GithubRootOrg": {
 			Parameter: moduleconfig.Parameter{
 				Field:   "GithubRootOrg",
-				Label:   "What's the root of the github org to create repositories in?",
+				Label:   "What's the root of the github organization that will own these repositories?",
 				Info:    "This should be github.com/<your-organization-name>",
 				Default: "github.com/",
 			},
-			Condition: KeyMatchCondition("ShouldPushRepositories", "y"),
-			Validate:  NoValidation,
+			Condition: NoCondition,
+			Validate:  ValidateOrganizationName,
 		},
 	}
 
diff --git a/internal/init/prompts.go b/internal/init/prompts.go
index fc33e0a8..b2c88078 100644
--- a/internal/init/prompts.go
+++ b/internal/init/prompts.go
@@ -105,6 +105,21 @@ func ValidateProjectName(input string) error {
 	return nil
 }
 
+// ValidateOrganizationName validates Organization Name field user input.
+func ValidateOrganizationName(input string) error {
+	// the first 62 char out of base64 and -
+	var organizationName = strings.TrimLeft(input, "github.com/")
+	var oName = regexp.MustCompile(`^[A-Za-z0-9-]{1,39}$`)
+	// error if char len is greater than 39
+	if len(organizationName) > constants.MaxOnameLength {
+		return errors.New("Invalid, Organization Name: (cannot exceed a max length of 39)")
+	}
+	if !oName.MatchString(organizationName) {
+		return errors.New("Invalid, Organization Name: (can only contain alphanumeric chars & '-')")
+	}
+	return nil
+}
+
 const infoBoxHeight = 4
 
 var currentLine int = infoBoxHeight