diff --git a/config/crd/patches/validation_in_linodeclustertemplates.yaml b/config/crd/patches/validation_in_linodeclustertemplates.yaml
index 579ae5542..b3b7b49bd 100644
--- a/config/crd/patches/validation_in_linodeclustertemplates.yaml
+++ b/config/crd/patches/validation_in_linodeclustertemplates.yaml
@@ -6,4 +6,7 @@
       type: string
       x-kubernetes-validations:
       - rule: 3 <= size(self) && size(self) <= 26
-        message: linode nodebalancer labels must be between 3..32 characters
+        message: >
+          custom validation:
+          template: must be between 3..26 characters,
+          linode nodebalancer: labels must be between 3..32 characters
diff --git a/config/crd/patches/validation_in_linodemachinetemplates.yaml b/config/crd/patches/validation_in_linodemachinetemplates.yaml
index 518d79602..817d30677 100644
--- a/config/crd/patches/validation_in_linodemachinetemplates.yaml
+++ b/config/crd/patches/validation_in_linodemachinetemplates.yaml
@@ -6,12 +6,22 @@
       type: string
       x-kubernetes-validations:
       - rule: 3 <= size(self) && size(self) <= 58
-        message: linode instance labels must be between 3..64 characters
-      # TODO: Combine these into one regex to validate ALL constraints on Linode instance labels at once?
-      # https://www.linode.com/docs/api/linode-instances/#linode-create
-      - rule: self.contains('^[a-z0-9](.*[a-z0-9])*$')
-        message: linode instance labels must begin and end with an alphanumeric character
-      - rule: self.contains('^[-_.[:alnum:]]*$')
-        message: linode instance labels may only consist of alphanumeric characters, hyphens (-), underscores (_) or periods (.)
+        message: >
+          custom validation:
+          template: must be between 3..58 characters,
+          linode instance: labels must be between 3..64 characters
+      - rule: self.matches('^[[:alnum:]]([-_.[:alnum:]]+[[:alnum:]])*$')
+        message: >
+          custom validation:
+          linode instance: labels:
+          must begin and end with an alphanumeric character,
+          may only consist of alphanumeric characters, hyphens (-), underscores (_) or periods (.),
+          cannot have two hyphens (--), underscores (__) or periods (..) in a row,
+          regex used for validation is: '^[[:alnum:]]([-_.[:alnum:]]+[[:alnum:]])*$',
+          see: https://www.linode.com/docs/api/linode-instances/#linode-create
+      # TODO: Consider combining this into the regex above to minimize time complexity
+      # See: https://github.com/google/cel-spec/blob/master/doc/langdef.md#time-complexity
       - rule: "!(self.contains('--') || self.contains('__') || self.contains('..'))"
-        message: linode instance labels cannot have two hyphens (--), underscores (__) or periods (..) in a row
+        message: >
+          custom validation:
+          linode instance: labels cannot have two hyphens (--), underscores (__) or periods (..) in a row