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If the server uses a self-signed certificate (or a certificate signed by an unknown CA), you will need to explicitly import server's certificate into the Java's trust keystore. (See instructions.) By default, the trust keystore is called cacerts and it resides in C:\Program Files\JIRA Client\jre\lib\security\cacerts. With the same method you used for setting the three properties described above, it's possible to specify a different location for cacerts: you need to set javax.net.ssl.trustStore property to </path/to/your/cacerts>, and, if the password is not default (changeit), set javax.net.ssl.trustStorePassword property.