diff --git a/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/KeyLocationResolver.java b/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/KeyLocationResolver.java
index adea6859..6922bbed 100644
--- a/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/KeyLocationResolver.java
+++ b/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/KeyLocationResolver.java
@@ -16,6 +16,7 @@
  */
 package io.smallrye.jwt.auth.principal;
 
+import java.io.IOException;
 import java.security.Key;
 import java.security.PublicKey;
 import java.security.cert.X509Certificate;
@@ -26,6 +27,7 @@
 import org.jose4j.jws.JsonWebSignature;
 import org.jose4j.jwx.JsonWebStructure;
 import org.jose4j.keys.resolvers.VerificationKeyResolver;
+import org.jose4j.lang.JoseException;
 import org.jose4j.lang.UnresolvableKeyException;
 
 import io.smallrye.jwt.KeyFormat;
@@ -63,6 +65,14 @@ public Key resolveKey(JsonWebSignature jws, List<JsonWebStructure> nestingContex
         Key theKey = tryAsVerificationJwk(jws);
 
         if (theKey == null) {
+            try {
+                if (httpsJwks != null && httpsJwks.getJsonWebKeys() != null && jws != null
+                        && jws.getKeyIdHeaderValue() != null) {
+                    throw PrincipalMessages.msg.unmatchedTokenKidException();
+                }
+            } catch (JoseException | IOException e) {
+                // ignore, if JWK is unavailable this was logged previously
+            }
             reportUnresolvableKeyException(authContextInfo.getPublicKeyContent(), authContextInfo.getPublicKeyLocation());
         }
         return theKey;
diff --git a/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/PrincipalMessages.java b/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/PrincipalMessages.java
index 57944558..a75c74b5 100644
--- a/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/PrincipalMessages.java
+++ b/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/PrincipalMessages.java
@@ -80,4 +80,8 @@ interface PrincipalMessages {
 
     @Message(id = 7020, value = "Required key identifier is null")
     UnresolvableKeyException nullKeyIdentifier();
+
+    @Message(id = 7021, value = "JWK set does not contain provided token 'kid'")
+    UnmatchedTokenKidException unmatchedTokenKidException();
+
 }
\ No newline at end of file
diff --git a/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/UnmatchedTokenKidException.java b/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/UnmatchedTokenKidException.java
new file mode 100644
index 00000000..49c14117
--- /dev/null
+++ b/implementation/jwt-auth/src/main/java/io/smallrye/jwt/auth/principal/UnmatchedTokenKidException.java
@@ -0,0 +1,31 @@
+/*
+ *   Copyright 2022 Red Hat, Inc, and individual contributors.
+ *
+ *   Licensed under the Apache License, Version 2.0 (the "License");
+ *   you may not use this file except in compliance with the License.
+ *   You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ *   Unless required by applicable law or agreed to in writing, software
+ *   distributed under the License is distributed on an "AS IS" BASIS,
+ *   WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ *   See the License for the specific language governing permissions and
+ *   limitations under the License.
+ */
+package io.smallrye.jwt.auth.principal;
+
+import org.jose4j.lang.UnresolvableKeyException;
+
+public class UnmatchedTokenKidException extends UnresolvableKeyException {
+
+    private static final long serialVersionUID = 1L;
+
+    public UnmatchedTokenKidException(String message) {
+        super(message);
+    }
+
+    public UnmatchedTokenKidException(String message, Throwable cause) {
+        super(message, cause);
+    }
+}
diff --git a/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/JWTHttpAuthenticationMechanism.java b/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/JWTHttpAuthenticationMechanism.java
index a5e8afda..3f0de763 100644
--- a/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/JWTHttpAuthenticationMechanism.java
+++ b/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/JWTHttpAuthenticationMechanism.java
@@ -41,6 +41,7 @@
 import io.smallrye.jwt.auth.principal.JWTAuthContextInfo;
 import io.smallrye.jwt.auth.principal.JWTParser;
 import io.smallrye.jwt.auth.principal.ParseException;
+import io.smallrye.jwt.auth.principal.UnmatchedTokenKidException;
 
 /**
  * A JAX-RS HttpAuthenticationMechanism prototype
@@ -97,7 +98,10 @@ public AuthenticationStatus validateRequest(HttpServletRequest request,
                 MechanismLogging.log.success();
                 return httpMessageContext.notifyContainerAboutLogin(jwtPrincipal, groups);
             } catch (ParseException e) {
-                if (e.getCause() instanceof UnresolvableKeyException) {
+                if (e.getCause() instanceof UnmatchedTokenKidException) {
+                    MechanismLogging.log.kidNotInJWkSet();
+                    return httpMessageContext.responseUnauthorized();
+                } else if (e.getCause() instanceof UnresolvableKeyException) {
                     MechanismLogging.log.noUsableKey();
                     return reportInternalError(httpMessageContext);
                 } else {
@@ -158,4 +162,4 @@ protected String getCookieValue(String cookieName) {
             return null;
         }
     }
-}
\ No newline at end of file
+}
diff --git a/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/MechanismLogging.java b/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/MechanismLogging.java
index 9927179a..40d7bf72 100644
--- a/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/MechanismLogging.java
+++ b/implementation/jwt-http-mechanism/src/main/java/io/smallrye/jwt/auth/mechanism/MechanismLogging.java
@@ -26,4 +26,8 @@ interface MechanismLogging extends BasicLogger {
     @LogMessage(level = Logger.Level.DEBUG)
     @Message(id = 11003, value = "Failed to resolve the key. Either corrupt or unavailable.")
     void noUsableKey();
+
+    @LogMessage(level = Logger.Level.DEBUG)
+    @Message(id = 11004, value = "JWK set does not contain provided token 'kid'")
+    void kidNotInJWkSet();
 }