diff --git a/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthenticationProviderUtils.java b/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthenticationProviderUtils.java
index 97bc402f4..99224cd73 100644
--- a/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthenticationProviderUtils.java
+++ b/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthenticationProviderUtils.java
@@ -17,6 +17,7 @@
 
 import org.springframework.security.authentication.AuthenticationProvider;
 import org.springframework.security.core.Authentication;
+import org.springframework.security.oauth2.core.OAuth2AccessToken;
 import org.springframework.security.oauth2.core.OAuth2AuthenticationException;
 import org.springframework.security.oauth2.core.OAuth2ErrorCodes;
 import org.springframework.security.oauth2.core.OAuth2RefreshToken;
@@ -55,6 +56,25 @@ static <T extends OAuth2Token> OAuth2Authorization invalidate(
 						(metadata) ->
 								metadata.put(OAuth2Authorization.Token.INVALIDATED_METADATA_NAME, true));
 
+		if (OAuth2AuthorizationCode.class.isAssignableFrom(token.getClass())) {
+			OAuth2Authorization.Token<OAuth2AccessToken> accessToken = authorization.getAccessToken();
+			if (accessToken != null && !accessToken.isInvalidated()) {
+				authorizationBuilder.token(
+						accessToken.getToken(),
+						(metadata) ->
+								metadata.put(OAuth2Authorization.Token.INVALIDATED_METADATA_NAME, true));
+			}
+
+			OAuth2Authorization.Token<OAuth2RefreshToken> refreshToken = authorization.getRefreshToken();
+			if (refreshToken != null && !refreshToken.isInvalidated()) {
+				authorizationBuilder.token(
+						refreshToken.getToken(),
+						(metadata) ->
+								metadata.put(OAuth2Authorization.Token.INVALIDATED_METADATA_NAME, true));
+			}
+
+		}
+
 		if (OAuth2RefreshToken.class.isAssignableFrom(token.getClass())) {
 			authorizationBuilder.token(
 					authorization.getAccessToken().getToken(),
diff --git a/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProvider.java b/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProvider.java
index cb8fb9021..51c8af241 100644
--- a/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProvider.java
+++ b/oauth2-authorization-server/src/main/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProvider.java
@@ -149,6 +149,13 @@ public Authentication authenticate(Authentication authentication) throws Authent
 		}
 
 		if (!authorizationCode.isActive()) {
+			if (authorizationCode.isInvalidated()) {
+				authorization = OAuth2AuthenticationProviderUtils.invalidate(authorization, authorizationCode.getToken());
+				this.authorizationService.save(authorization);
+				if (this.logger.isWarnEnabled()) {
+					this.logger.warn(LogMessage.format("Invalidated authorization tokens previously issued based on the authorization code"));
+				}
+			}
 			throw new OAuth2AuthenticationException(OAuth2ErrorCodes.INVALID_GRANT);
 		}
 
@@ -169,7 +176,12 @@ public Authentication authenticate(Authentication authentication) throws Authent
 				.authorizationGrant(authorizationCodeAuthentication);
 		// @formatter:on
 
-		OAuth2Authorization.Builder authorizationBuilder = OAuth2Authorization.from(authorization);
+		// @formatter:off
+		OAuth2Authorization.Builder authorizationBuilder = OAuth2Authorization.from(authorization)
+				// Invalidate the authorization code as it can only be used once
+				.token(authorizationCode.getToken(), metadata ->
+						metadata.put(OAuth2Authorization.Token.INVALIDATED_METADATA_NAME, true));
+		// @formatter:on
 
 		// ----- Access token -----
 		OAuth2TokenContext tokenContext = tokenContextBuilder.tokenType(OAuth2TokenType.ACCESS_TOKEN).build();
@@ -250,9 +262,6 @@ public Authentication authenticate(Authentication authentication) throws Authent
 
 		authorization = authorizationBuilder.build();
 
-		// Invalidate the authorization code as it can only be used once
-		authorization = OAuth2AuthenticationProviderUtils.invalidate(authorization, authorizationCode.getToken());
-
 		this.authorizationService.save(authorization);
 
 		if (this.logger.isTraceEnabled()) {
@@ -305,5 +314,4 @@ private SessionInformation getSessionInformation(Authentication principal) {
 		}
 		return sessionInformation;
 	}
-
 }
diff --git a/oauth2-authorization-server/src/test/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProviderTests.java b/oauth2-authorization-server/src/test/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProviderTests.java
index d0bc3613e..9e82fd53a 100644
--- a/oauth2-authorization-server/src/test/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProviderTests.java
+++ b/oauth2-authorization-server/src/test/java/org/springframework/security/oauth2/server/authorization/authentication/OAuth2AuthorizationCodeAuthenticationProviderTests.java
@@ -271,6 +271,12 @@ public void authenticateWhenInvalidatedCodeThenThrowOAuth2AuthenticationExceptio
 				.extracting(ex -> ((OAuth2AuthenticationException) ex).getError())
 				.extracting("errorCode")
 				.isEqualTo(OAuth2ErrorCodes.INVALID_GRANT);
+
+		ArgumentCaptor<OAuth2Authorization> authorizationCaptor = ArgumentCaptor.forClass(OAuth2Authorization.class);
+		verify(this.authorizationService).save(authorizationCaptor.capture());
+		OAuth2Authorization updatedAuthorization = authorizationCaptor.getValue();
+		assertThat(updatedAuthorization.getAccessToken().isInvalidated()).isTrue();
+		assertThat(updatedAuthorization.getRefreshToken().isInvalidated()).isTrue();
 	}
 
 	// gh-290