When enabling TCPS on the listener you notice the following error when starting the listener:
LSNRCTL for 64-bit Windows: Version 19.0.0.0.0 - Production on 25-AUG-2023 12:44:15
Copyright (c) 1991, 2020, Oracle. All rights reserved.
Connecting to (DESCRIPTION=(ADDRESS=(PROTOCOL=TCPS)(HOST=MyOracleServer)(PORT=2484)))
ORA-28864: SSL connection closed gracefully
TNS-12560: TNS:protocol adapter error
TNS-00542: SSL Handshake failed
64-bit Windows Error: 28864: Unknown error
Connecting to (DESCRIPTION=(ADDRESS=(PROTOCOL=IPC)(KEY=protect)))
STATUS of the LISTENER
------------------------
Alias LISTENER
Version TNSLSNR for 64-bit Windows: Version 19.0.0.0.0 - Production
Start Date 25-AUG-2023 12:44:02
Uptime 0 days 0 hr. 0 min. 13 sec
Trace Level support
Security ON: Local OS Authentication
SNMP OFF
Listener Parameter File C:\Oracle\Product\19.3.0.0\db_1\network\admin\listener.ora
Listener Log File C:\oracle\diag\tnslsnr\Oracle16\listener\alert\log.xml
Listener Trace File C:\oracle\diag\tnslsnr\Oracle16\listener\trace\ora_2396_6372.trc
Listening Endpoints Summary...
(DESCRIPTION=(ADDRESS=(PROTOCOL=tcps)(HOST=MyOracleServer)(PORT=2484)))
(DESCRIPTION=(ADDRESS=(PROTOCOL=ipc)(PIPENAME=\\.\pipe\protectipc)))
Services Summary...
Service "CLRExtProc" has 1 instance(s).
Instance "CLRExtProc", status UNKNOWN, has 1 handler(s) for this service...
The command completed successfully
Release : 19
This can be caused by lack of permissions on the wallet files. So when you create a wallet and certs using orapki utility, by default it looks like it disables inheritance after creating the files under the wallet directory. The user which is used to run the listener service in services.msc needs to have full permissions over this directory.
Fix permissions or enable inheritance on all files under the wallet folder.