diff --git a/config/crd/patches/validation_in_linodeclusters.yaml b/config/crd/patches/validation_in_linodeclusters.yaml
index 6ec423dca..d0c66017c 100644
--- a/config/crd/patches/validation_in_linodeclusters.yaml
+++ b/config/crd/patches/validation_in_linodeclusters.yaml
@@ -6,4 +6,4 @@
       type: string
       x-kubernetes-validations:
       - rule: 3 <= size(self) && size(self) <= 32
-        message: linode nodebalancer labels must be between 3..32 characters
+        message: "custom validation: linode nodebalancer: labels must be between 3..32 characters"
diff --git a/config/crd/patches/validation_in_linodemachines.yaml b/config/crd/patches/validation_in_linodemachines.yaml
index a2f008594..c5a27e154 100644
--- a/config/crd/patches/validation_in_linodemachines.yaml
+++ b/config/crd/patches/validation_in_linodemachines.yaml
@@ -7,11 +7,15 @@
       x-kubernetes-validations:
       - rule: 3 <= size(self) && size(self) <= 64
         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-z].*[a-z]$')
-        message: linode instance labels must begin and end with an alphanumeric character
-      - rule: self.contains('^[-_.a-z0-9]$')
-        message: linode instance labels may only consist of alphanumeric characters, hyphens (-), underscores (_) or periods (.)
+      - 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: We need to combine this into one regex 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"
diff --git a/config/crd/patches/validation_in_linodevpcs.yaml b/config/crd/patches/validation_in_linodevpcs.yaml
index d190af7b0..116b831c0 100644
--- a/config/crd/patches/validation_in_linodevpcs.yaml
+++ b/config/crd/patches/validation_in_linodevpcs.yaml
@@ -7,9 +7,14 @@
       x-kubernetes-validations:
       - rule: 1 <= size(self) && size(self) <= 64
         message: vpc labels must be between 3..64 characters
-      # TODO: Combine these into one regex to validate ALL constraints on VPC labels at once?
-      # https://www.linode.com/docs/api/vpcs/#vpc-create
-      - rule: self.matches('^[-a-z0-9]$')
-        message: vpc labels can only contain ASCII letters, numbers, and hyphens (-)
+      - rule: self.matches('^[-[:alnum:]]+$')
+        message: >
+          custom validation: linode vpc: labels:
+          can only contain ASCII letters, numbers, and hyphens (-),
+          cannot have two consecutive hyphens (--);
+          regex used for validation is: '^[-[:alnum:]]+$',
+          see: https://www.linode.com/docs/api/vpcs/#vpc-create
+      # TODO: We need to combine this into one regex to minimize time complexity 🥺
+      # See: https://github.com/google/cel-spec/blob/master/doc/langdef.md#time-complexity
       - rule: "!self.contains('--')"
-        message: vpc labels cannot have two consecutive hyphens (--)
+        message: "custom validation: linode vpc: labels cannot have two consecutive hyphens (--)"