Let me explain what is happening:

* Database: Oracle 19c
* Apex: 19.1.0.00.15
* ORDS standalone is 19.1.0.r0921545

I did the tasks to configure an Apex Social Sign In to Microsoft AAD without almost any issue:

* I created the authentication method in Apex.
* I register my application and get the web credentials in Azure.
* I created a wallet in my database with the root CA Microsoft certificates and configured the instance settings to usee that wallet.
* My wallet in the database server contains the property auto\_login to avoid using passwords.
* I created the ACEs entries to allow connection to the login.microsoftonline.com in the port 443
* Although it is not important for the purpose of the question itself and the error that is producing, just comment that I configured the wallet settings in the internal workspace in order to provide access to the wallet to the apex applications.

For some weeks the process was working fine, I was having a perfect Single Sing on mechanism for all my apex applications in the different workspaces. However, since some days ago, I am getting always the same error:

**ORA-29024: Certificate validation failure**

After some digging I realise that someone has configured a PROXY for outgoing traffic. Before even trying in Apex, I tried in SQL using APEX\_WEB\_SERVICE

Request with proxy settings to login.microsoftonline.com

```
select apex_web_service.make_rest_request(
    p_url         => 'https://login.microsoftonline.com',
    p_http_method => 'GET',
    p_wallet_path => 'file:/home/oracle/wallet',
    p_wallet_pwd => 'MyPassword' ,
    p_proxy_override => 'http://myproxy:myport'
  7  ) from dual;
ERROR:
ORA-29273: HTTP request failed
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1035
ORA-29024: Certificate validation failure
ORA-06512: at "SYS.UTL_HTTP", line 380
ORA-06512: at "SYS.UTL_HTTP", line 1148
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 934
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1580
ORA-06512: at "APEX_190100.WWV_FLOW_WEBSERVICES_API", line 408
ORA-06512: at line 1

```

Request without proxy settings, just to see if I can get there

```
SQL> select apex_web_service.make_rest_request(
  2      p_url         => 'https://login.microsoftonline.com',
  3      p_http_method => 'GET',
  4      p_wallet_path => 'file:/home/oracle/wallet'
  5* ) from dual
SQL> /
ERROR:
ORA-29273: HTTP request failed
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1035
ORA-29024: Certificate validation failure
ORA-06512: at "SYS.UTL_HTTP", line 380
ORA-06512: at "SYS.UTL_HTTP", line 1148
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 934
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1580
ORA-06512: at "APEX_190100.WWV_FLOW_WEBSERVICES_API", line 408
ORA-06512: at line 1

```

Request to google using Proxy settings

```
select apex_web_service.make_rest_request(
    p_url         => 'https://google.com',
    p_http_method => 'GET',
    p_wallet_path => 'file:/home/oracle/wallet',
    p_wallet_pwd => 'MyPassword' ,
  6      p_proxy_override => 'http://myproxy:myport'
  7  ) from dual ;
ERROR:
ORA-29273: HTTP request failed
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1035
ORA-29024: Certificate validation failure
ORA-06512: at "SYS.UTL_HTTP", line 380
ORA-06512: at "SYS.UTL_HTTP", line 1148
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 934
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1580
ORA-06512: at "APEX_190100.WWV_FLOW_WEBSERVICES_API", line 408
ORA-06512: at line 1

```

Request to google without proxy settings

```
SQL> select apex_web_service.make_rest_request(
  2      p_url         => 'https://google.com',
  3      p_http_method => 'GET',
  4      p_wallet_path => 'file:/home/oracle/wallet'
  5* ) from dual
SQL> /
ERROR:
ORA-29273: HTTP request failed
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1035
ORA-12535: TNS:operation timed out
ORA-06512: at "SYS.UTL_HTTP", line 380
ORA-06512: at "SYS.UTL_HTTP", line 1148
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 934
ORA-06512: at "APEX_190100.WWV_FLOW_WEB_SERVICES", line 1580
ORA-06512: at "APEX_190100.WWV_FLOW_WEBSERVICES_API", line 408
ORA-06512: at line 1

```

My questions are the following:

* It is a network problem or a proxy issue regarding inbound/outbound
traffic ? I can reach Microsoft but not Google in the port 443 when I don't specify proxy.
* Why am I getting invalid certificate when it has nothing to do with
the certificates ?
* How can I setup my APEX to use authentication on Azure or any other
provider for that matter when I have a proxy in the middle ?
* As I use ORDS standalone, am I allow to keep using it or I need a
reverse proxy with Tomcat ?

I tried to configure the ACE to use HTTP\_PROXY in the ports by running

```
begin
  sys.dbms_network_acl_admin.append_host_ace(
    host        => 'myproxyserver'
   ,lower_port  => 8080
   ,upper_port  => 8080
   ,ace         => xs$ace_type(
      privilege_list     => xs$name_list('http_proxy')
     ,granted            => true
     ,principal_name     => 'MY_PRINCIPAL'
     ,principal_type     => XS_ACL.PTYPE_DB
    )
  );
end;
/

```

Even I grant to the ACE privileges over the wallet

```
SET SERVEROUTPUT ON
BEGIN
  DBMS_NETWORK_ACL_ADMIN.APPEND_WALLET_ACE
  (
    WALLET_PATH => 'file:/home/oracle/wallet',
    ACE => XS$ACE_TYPE(
                        PRIVILEGE_LIST => XS$NAME_LIST('use_passwords','use_client_certificates'),
                        PRINCIPAL_NAME => 'MY_PRINCIPAL',
                        PRINCIPAL_TYPE => XS_ACL.PTYPE_DB
                      )
  );
EXCEPTION WHEN OTHERS THEN
  DBMS_OUTPUT.PUT_LINE('Error while configuring ACL for wallet: '|| SQLERRM);
END;
/

```

but I am still getting the same error all over.

Any help would be appreciated!
Thank you
['https://Stackoverflow.com/questions/62851314', 'https://Stackoverflow.com', 'https://Stackoverflow.com/users/13755538/']
I had issue like this, it seems Oracle SSL library has some bugs. Finally I implemented some Java Source for OJVM, please read my answer here: <https://stackoverflow.com/a/60152830/11272044>
In my understanding,you will need to do following(in addition to what you did) :

1. login to Apex as administrator
2. From settings, go to 'Wallet'
3. Add Wallet path(absolute path with prefix 'file://' and password you used for creating wallet

Now, your problem should be solved.