diff --git a/CHANGELOG/CHANGELOG-1.30.md b/CHANGELOG/CHANGELOG-1.30.md
index b269ada4bab..c87cfd0d87f 100644
--- a/CHANGELOG/CHANGELOG-1.30.md
+++ b/CHANGELOG/CHANGELOG-1.30.md
@@ -1584,7 +1584,7 @@ name | architectures
    ([#123344](https://github.com/kubernetes/kubernetes/pull/123344), [@nilekhc](https://github.com/nilekhc))
 - When configuring a JWT authenticator:
   
-  If `username.expression` used 'claims.email', then 'claims.email_verified' must have been used in `username.expression` or `extra[*].valueExpression` or `claimValidationRules[*].expression`. An example claim validation rule expression that matches the validation automatically applied when `username.claim` is set to 'email' is 'claims.?email_verified.orValue(true)'.
+  If `username.expression` used 'claims.email', then 'claims.email_verified' must have been used in `username.expression` or `extra[*].valueExpression` or `claimValidationRules[*].expression`. An example claim validation rule expression that matches the validation automatically applied when `username.claim` is set to 'email' is 'claims.?email_verified.orValue(true) == true'.
    ([#123737](https://github.com/kubernetes/kubernetes/pull/123737), [@enj](https://github.com/enj))
 - `readOnly` volumes now support recursive read-only mounts for kernel versions >= 5.12."
    ([#123180](https://github.com/kubernetes/kubernetes/pull/123180), [@AkihiroSuda](https://github.com/AkihiroSuda))
@@ -2416,7 +2416,7 @@ name | architectures
   If username.expression uses 'claims.email', then 'claims.email_verified' must be used in
   username.expression or extra[*].valueExpression or claimValidationRules[*].expression.
   An example claim validation rule expression that matches the validation automatically
-  applied when username.claim is set to 'email' is 'claims.?email_verified.orValue(true)'. ([#123737](https://github.com/kubernetes/kubernetes/pull/123737), [@enj](https://github.com/enj)) [SIG API Machinery and Auth]
+  applied when username.claim is set to 'email' is 'claims.?email_verified.orValue(true) == true'. ([#123737](https://github.com/kubernetes/kubernetes/pull/123737), [@enj](https://github.com/enj)) [SIG API Machinery and Auth]
 
 ### Feature
 
diff --git a/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1alpha1/types.go b/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1alpha1/types.go
index dee2c115a15..0a50799c26e 100644
--- a/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1alpha1/types.go
+++ b/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1alpha1/types.go
@@ -352,7 +352,9 @@ type ClaimMappings struct {
 	// If username.expression uses 'claims.email', then 'claims.email_verified' must be used in
 	// username.expression or extra[*].valueExpression or claimValidationRules[*].expression.
 	// An example claim validation rule expression that matches the validation automatically
-	// applied when username.claim is set to 'email' is 'claims.?email_verified.orValue(true)'.
+	// applied when username.claim is set to 'email' is 'claims.?email_verified.orValue(true) == true'. By explicitly comparing
+	// the value to true, we let type-checking see the result will be a boolean, and to make sure a non-boolean email_verified
+	// claim will be caught at runtime.
 	//
 	// In the flag based approach, the --oidc-username-claim and --oidc-username-prefix are optional. If --oidc-username-claim is not set,
 	// the default value is "sub". For the authentication config, there is no defaulting for claim or prefix. The claim and prefix must be set explicitly.
diff --git a/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1beta1/types.go b/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1beta1/types.go
index a0e13593b3b..72fe602b95d 100644
--- a/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1beta1/types.go
+++ b/staging/src/k8s.io/apiserver/pkg/apis/apiserver/v1beta1/types.go
@@ -323,7 +323,9 @@ type ClaimMappings struct {
 	// If username.expression uses 'claims.email', then 'claims.email_verified' must be used in
 	// username.expression or extra[*].valueExpression or claimValidationRules[*].expression.
 	// An example claim validation rule expression that matches the validation automatically
-	// applied when username.claim is set to 'email' is 'claims.?email_verified.orValue(true)'.
+	// applied when username.claim is set to 'email' is 'claims.?email_verified.orValue(true) == true'. By explicitly comparing
+	// the value to true, we let type-checking see the result will be a boolean, and to make sure a non-boolean email_verified
+	// claim will be caught at runtime.
 	//
 	// In the flag based approach, the --oidc-username-claim and --oidc-username-prefix are optional. If --oidc-username-claim is not set,
 	// the default value is "sub". For the authentication config, there is no defaulting for claim or prefix. The claim and prefix must be set explicitly.
diff --git a/staging/src/k8s.io/apiserver/pkg/apis/apiserver/validation/validation_test.go b/staging/src/k8s.io/apiserver/pkg/apis/apiserver/validation/validation_test.go
index 2e39d375f1c..6d761b59318 100644
--- a/staging/src/k8s.io/apiserver/pkg/apis/apiserver/validation/validation_test.go
+++ b/staging/src/k8s.io/apiserver/pkg/apis/apiserver/validation/validation_test.go
@@ -585,6 +585,61 @@ func TestValidateAuthenticationConfiguration(t *testing.T) {
 			},
 			want: "",
 		},
+		{
+			name: "valid authentication configuration that uses verified email via claim validation rule",
+			in: &api.AuthenticationConfiguration{
+				JWT: []api.JWTAuthenticator{
+					{
+						Issuer: api.Issuer{
+							URL:       "https://issuer-url",
+							Audiences: []string{"audience"},
+						},
+						ClaimValidationRules: []api.ClaimValidationRule{
+							{
+								// By explicitly comparing the value to true, we let type-checking see the result will be
+								// a boolean, and to make sure a non-boolean email_verified claim will be caught at runtime.
+								Expression: `claims.?email_verified.orValue(true) == true`,
+							},
+						},
+						// allow email claim only when email_verified is present and true
+						ClaimMappings: api.ClaimMappings{
+							Username: api.PrefixedClaimOrExpression{
+								Expression: `{claims.?email: "panda"}`,
+							},
+						},
+					},
+				},
+			},
+			want: "",
+		},
+		{
+			name: "valid authentication configuration that uses verified email via claim validation rule incorrectly",
+			in: &api.AuthenticationConfiguration{
+				JWT: []api.JWTAuthenticator{
+					{
+						Issuer: api.Issuer{
+							URL:       "https://issuer-url",
+							Audiences: []string{"audience"},
+						},
+						ClaimValidationRules: []api.ClaimValidationRule{
+							{
+								// This expression was previously documented in the godoc for the JWT authenticator
+								// and was incorrect. It was changed to the above expression in the previous test case.
+								// Testing the old expression here to confirm it fails validation.
+								Expression: `claims.?email_verified.orValue(true)`,
+							},
+						},
+						// allow email claim only when email_verified is present and true
+						ClaimMappings: api.ClaimMappings{
+							Username: api.PrefixedClaimOrExpression{
+								Expression: `{claims.?email: "panda"}`,
+							},
+						},
+					},
+				},
+			},
+			want: `[jwt[0].claimValidationRules[0].expression: Invalid value: "claims.?email_verified.orValue(true)": must evaluate to bool, jwt[0].claimMappings.username.expression: Invalid value: "{claims.?email: \"panda\"}": claims.email_verified must be used in claimMappings.username.expression or claimMappings.extra[*].valueExpression or claimValidationRules[*].expression when claims.email is used in claimMappings.username.expression]`,
+		},
 		{
 			name: "valid authentication configuration",
 			in: &api.AuthenticationConfiguration{